sailboat rental anna maria island

Welcome aboard Zig Zag Your Sailboat Charter

Cruise aboard our 30' catalina yacht.

Sailing in Tampa Bay, from Anna Maria Island, Florida

Experience The Joy Of Sailing

Enjoy a sailboat cruise on the beautiful emerald green waters of Tampa Bay and the Gulf of Mexico, just minutes from Bradenton, Florida. Take a turn at the helm or just relax and watch the dolphins play. Your cruise with Spice Sailing Charters will be the highlight of your vacation.

Other services available include sailing lessons and memorials for your loved ones with At Sea Burials.

Witness Our Glorious Tampa Bay Sunsets

Charter a sunset cruise aboard, Zig Zag, a comfortable and spacious 30 foot sailboat. Bring some wine and cheese, and be prepared to take home spectacular memories and awesome photos of your sailing experience off the coast of Anna Maria Island.

Sail With Captain Ed Hartung

• U.S.C.G. Licensed and charter captain since 1988
• 100 Ton Masters License from the United States Coast Guard
• Cruises and races to Mexico, Cuba and the Virgin Islands
• Over 25 years of sailboat chartering experience in Tampa Bay and the Gulf of Mexico
• His sailing experience has included local and long distance yacht deliveries
• Sailboat charters serving Anna Maria Island, Holmes Beach, Longboat Key, Bradenton, Sarasota, Palmetto, Ellenton, in the Tampa Bay area

"Ed Hartung is one of The Finest, most safety conscious sailors, I have ever sailed with."    Tom Newmann

"Ed is a very skilled and experienced sailboat charter captain. But more importantly, he will go well out of his way to ensure that all his passengers have a wonderful time aboard Zig Zag."    Jay Winters

Checkout Learn Sailing Fun and Easy ($9. 95 )

• Become an Anchor Captain
• List Your Boat

Basic Information

Anna Maria Island Yacht Rental

Yacht rental anna maria island | boat rentals and yacht charters in anna maria island, thank you for making anchor the #1 yacht rental company in anna maria island, anna maria island yacht rentals .

Welcome to Anna Maria Island, FL, home to some of the most beautiful beaches on the west coast of Florida! Anchor has a beautiful fleet of boats and yachts available for rent or charter on Anna Maria Island. Anna Maria Island is the perfect yacht charter destination, with intracoastal waterways to view mansions, sandbars for swimming and water activities, and a large selection of boats and yacht charters to choose from. Whether you're celebrating a bachelor or bachelorette party, birthday, or just hangin' with your crew, Anchor is the top rated yacht rental company in Anna Maria Island. 

Day Charters

Anna Maria Island has plenty to offer for a perfect yacht charter. We offer 4 hour rentals, 6 hour rentals, and full-day rentals. We also offer multi-day trips if you want to visit destinations like Fort Myers , Cape Coral , South Seas, Marco Island, and Florida Keys. Day charters are an affordable way for you and your crew to rent a private yacht with Captain and Crew included. Also included in the price of your charter is local cruising fuel, cleaning fees, service fees & taxes, and even some gratuity on most charter listings. Most of our boats have a 13 guest max, not including the Captain and Crew. So grab 12 of your best friends and head out for a Anna Maria Island yacht charter with Anchor!

Find the perfect yacht rental in Anna Maria Island

Anchor has hundreds of boats and yachts available for rent with a Captain. You can shop and browse boats and filter by date, location (using the map), size, budget, and much more. Book a boat or yacht with confidence with our transparent and all-inclusive pricing. Never worry about hidden fees or additional costs, unless you want to add provisions to your charter. Finding the perfect yacht charter in Anna Maria Island is super easy with Anchor.

Boat rentals and yacht charters to Egmont Key

Egmont Key is a popular boating destination with beautifully clear / turquoise water. Egmont Key is located just south of St. Pete, FL and just north of Anna Maria Island , so if your boat or yacht is departing from Anna Maria Island, you can book a 4 hour trip, or save money with the discounted full-day (8 hour) yacht charter options. 

Boat rentals and yacht charters to Jewfish Key

Jewfish Key is a popular 38 acre island located near Sarasota and Anna Maria Island. This exquisite island oasis is one of the most popular destinations on the west coast of Florida. The sandbar at the western part of the island is excellent for relaxing and exploring for sea creatures. The water is clear with a turquoise hue.  Jewfish Key is a local favorite anchoring location for yacht charters to get in the water, swim, play, and have a lunch on the aft deck.

Weather in Anna Maria Island

Always keep in mind the weather when planning your yacht rental experience. Anna Maria Island is an ideal location for a yacht charter, either while on vacation or “staycation” because of the wonderful weather patterns. Located just above the tropical divide, the winters range in the 70°s and summers in the 90°s, there's no wrong time to visit. While it may rain frequently in Anna Maria Island, the storms are almost always scattered and very short in duration, often times only lasting a few minutes and then the sun is shining again. If you're traveling to Anna Maria Island in the cooler months of the year, be sure to pack some layers to wear while on your boating trip, especially if you plan to go yachting in the evening. If you're traveling during the summer months, remember to stay hydrated and take some extra precautions when it comes to sun care.

When planning to rent a yacht in Anna Maria Island, your Captain will keep an eye on the weather patterns. The Captain will warn you of any weather that could cause your yacht charter to be cancelled, rescheduled, or departure time pushed back. Safety is always our top priority.

Other popular yacht charter destinations near Anna Maria Island

Anna Maria Island is located on the west coast of Florida and is nestled near several other wonderful boating and yachting destinations, so if you can't find the boat rental or yacht charter you're looking for in Anna Maria Island, check out these other amazing locations. Sarasota and St. Petersburg, FL are the nearest yachting destinations. Tampa Bay has 75 boats and yachts available and is about 1 hour north of Anna Maria Island.   Ft. Myers and Cape Coral are about an 1-1.5 hour drive south and located below the tropical divide for warmer weather in the winter months.

How much does it cost to rent a yacht in Anna Maria Island?

The average cost to rent a yacht in anna maria island is $2200.00 (usd).

Average cost of a 4 hour yacht rental = $2200.00*

Average cost of a 6 hour yacht rental = $2900.00*

Average cost of a 8 yacht rental = $3300.00*

*The average cost of a yacht charter or yacht rental can differ based on the size of the boat and the year the boat was manufactured. Newer boats are more expensive, but they are cleaner and offer nicer amenities. And bigger boats are typically more expensive, but they offer often more space, amenities, crew, and overall experience. 

Welcome to Bimini Bay Sailing Lessons

Small sailboat sailing school.

I sold my last sailboat in July, 2023. I will still give occasional lessons for individuals who own their own small powerboat or sailboat.

Have a new Keelboat or Powerboat? I give small keelboat and small motorboat lessons on your boat, covering such topics as docking, backing up, pivot turns, and more as I share local knowledge of our waterways...

Bimini Bay is a beautiful, sheltered body of water nestled inside Anna Maria Island. It is the perfect, safe place to learn to sail -- and we often see dolphins! Bimini Bay Sailing is just minutes from Holmes Beach, Longboat Key, and Bradenton, snuggled between Tampa Bay and the Gulf of Mexico. During the last part of your saling lesson we usually sail just off the shore of Anna Maria Island into Tampa Bay, with a clear view of the Sunshine Skyway, Egmont Key and the Anna Maria Pier.

Take Sailing Lessons on the very stable WindRider 17 Trimaran, with a quiet electric motor for uncertain breezes. Or at your location on your own small dinghy sailboat or keelboat. I also offer powerboat docking lessons on your own boat.

Learn how to use a mainsheet, jib sheets, and a furling line. learn how to tack, jibe, and how to rig a sailboat. learn your basic points of sail. students usually sail at least half of the time on their own..

If you already know how to sail and you want to rent a Trimaran, for your safety and pleasure, I will still do a skills and safety review. Then I'll go out with you as your coach/guide, on the same sailboat, but you will do almost all of the sailing. This is to make your experience as safe and pleasant as possible.

Captain Floyd Jay Winters , an instructor for Bimini Bay Sailing since 2012, has taken over the helm of the Anna Maria Island small sailing school. (He is fully vaccinated.) To schedule a sailing lesson, you can reach Coach Jay Winters at 941.730.2719 or click on the [ Contact ] link.

I encourage a follow up session to refine your skills and have to opportunity to get more sailing time on your own. Parents or spouses are welcome to watch the sailing class and take photos of their kids or spouse as they learn to sail. Click the [ Lessons ] link for more information on what is covered.

Click the [ Photos ] link to see beautiful photos of Sunfish at Bimini Bay Sailing School.

A Father and Son Tacking a Sunfish (29 seconds)

For the past 11 years, Bimini Bay Sailing has offered a sailing summer camp through the Anna Maria Island Community Center. And once again this past June 2022, fourteen young sailors had the opportunity to safely experience the excitement of their first exposure to sailing during our mini sailing camps at Bimini Bay.

Receive sailing lessons at our small sailing school or just refresh your sailing skills in beautiful Bimini Bay. The magical waters around Anna Maria Island are warm, clear, and uncrowded.

Arial Map 1    Arial Map 2

Bimini Bay Sailing, Anna Maria Island , Florida

Anna Maria Island's best boat rental, fishing charters and Island excursions!

Boat Rentals

The shady lady.

The SHADY LADY Seats 8 people

- 4 hours • 6 hours • Full day and Weekly

Call for discounts 

- Starting @ $450.00 

The Big "B"

The Big "B" Seats up to 12 people

- 4 Hours • 6 hours • Full day and Weekly 

- Call for discounts

- Starting @ $450.00

Captained Excurions

Join us for an unforgettable adventure to Beer Can Island, Passage Key and Egmont Key, where our experienced captains will guide you through the best spots to explore.

Beer Can Island , Experience the ultimate adventure on our charter to Beer Can Island! Discover stunning beaches and diverse wildlife while fishing for snook, redfish, and trout. Savor a cold drink and witness the breathtaking Gulf of Mexico sunset for an unforgettable experience.

Passage Key boasts stunning white sand and crystal-clear waters, making it a must-visit destination for beach lovers and boaters. Visitors can spot a variety of wildlife, including sea turtles and manatees, while also enjoying fishing in the surrounding waters. The refuge plays a vital role in maintaining the health of the Gulf of Mexico ecosystem.

Egmont Key is a must-visit destination, with its historical landmarks, including the Egmont Key Lighthouse and Fort Dade, which offer a glimpse into the rich history of this small island. As a protected wildlife refuge, Egmont Key is also home to a diverse array of wildlife, including sea turtles, dolphins, manatees, and over 200 species of birds. - 4 hours • 6 hours • Full day with Captain

- Staring at $650.00

Looking to take your boating experience to 

This boat is perfect for those looking for a relaxing day with the family, an exciting excursion swimming with dolphins and manatees, or a customized experience tailored to your interests and preferences. With this boat, you'll be able to discover hidden beaches and sandbars, witness the wonder of dolphin pods, and visit the best restaurants and bars on the water. Don't settle for a slow and cramped boat ride, upgrade to the Axopar Suntop for the ultimate luxury powerboat experience. Book your trip today and make memories that will last a lifetime! If you have any questions please message me and I will be more than happy to answer them.  

-4 Hours • 6 hours • Full day with Captain

- Starting at $600.00

Fishing Charters

Half day fishing charters.

We offer inshore fishing trips for  Bradenton, Anna Maria Island and Palmetto, Florida. On our morning trips we will be fishing for snook, redfish, tarpon, trout, snapper, cobia, flounder, and many more inshore species that live in the Tampa Bay area. We offer two 4 hour time slots.  Let Captain Jon get you on those fish, so you can get them on your grill!!!

Dinner and Drinks

Boozy brunch excursion ~ seasonal ~ sundays only.

NEW FOR 2023 ~ Introducing the Boozy Brunch Boat Rental Package! 

Start your morning off right with a relaxing boat ride to a waterfront restaurant where you'll enjoy a delicious brunch with bottomless mimosas. Our package includes the boat rental, captain, and brunch reservation, so all you have to do is show up and enjoy. It's the perfect way to spend a lazy Sunday with friends or family. Don't miss out on this unforgettable brunch experience on the water!

Seasonal Feb through April • Sept through Nov.

Call to book May through Aug. 

Availability will be granted if no other bookings

- 3.5 Hours with Captain starts at 10am finishes at 1:30pm

Captained Bar Hoppin' By Boat

Looking for a fun boating experience with a touch of local charm? Our Bar Hoppin' By Boat package with captain is the perfect choice. Cruise along the water with a knowledgeable and experienced captain while enjoying a bottle of fine wine or beer while we make our way to dockside bars in AMI and the Manatee River.

With our expertly curated selection of restaurants and local watering holes, you're sure to have an unforgettable day on the water. Book now to experience the ultimate in luxury boating.

- Staring at $625

Meet our Captains

Captain adrien.

As a kid, I grew up fishing and boating on the Chesapeake Bay. It was there I spent many summers and I fell in love with boating. After moving to North Carolina, my love for boating only grew. But it was here in Florida I decided to turn my passion into my career. That is when our company Castaway was born. 

Captain Jon

 Hi my name is Capt Jon. I am a Georgia native but have been operating as a captain for the last 9 years in Tampa bay. I have plenty fishing knowledge as a charter captain. I am a people person and love my job as a captain. Let’s get out there and have a memorable day! 

We aim to please!

We offer a host of services and custom sand bar and island excursions.  Our add on service will make your experience a memorable one.  From our floating Lilly pads to our custom in house charcuterie will keep you coming back.

Get in Touch!

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Send us a message with any comments, questions, or scheduling concerns. We will get back to you soon!

Castaway Boat Rentals and Charter

941-405-3421

Copyright © 2023 Castaway Boat Rentals- All Rights Reserved.

• Privacy Policy
• Terms and Conditions

This website uses cookies.

We use cookies to analyze website traffic and optimize your website experience. By accepting our use of cookies, your data will be aggregated with all other user data.

• Like Us On Facebook
• Leave Us a Google Review
• Follow Us On Instagram

5 Star Rated Service!

(941) 504-5100

• [email protected]

Boat & Jet Ski Rentals Anna Maria Island

Serving  Boat Rentals in Anna Maria Island , and  Jet Ski Rentals in Anna Maria Island

Rent From Seaside Island Adventures today to start you adventure on the water!

About Seaside Island Adventures

Seaside Island Adventures is a professional boat and jet ski rental company in Anna Maria Island. Our company strives to always provide a fun and safe boating experience to each of our clients. Boat rentals in Anna Maria Island are a great way for people to view the island different islands, keys, and sand bars! Jet ski rentals in Anna Maria Island give you the opportunity to do the same thing as the boat, and/or you can rent it for an hour or two, to experience the fun of being on a jet ski. Give us a call today to book your adventure!

To book your boat and/or jet ski rental, please give us a call at: (941) 504-5100

Available Boat & Jet Ski Rentals

Seaside Island Adventures provides a variety of options for jet ski and boat rentals.

We have several boats for rent in Anna Maria Island, such as Tahoe T18 and a Trophy T22cc.

When in comes to jet skis, we thrive in having the best jet ski rentals in Anna Maria Island . We have the newest jet ski for rent on the island!

23' Trophy Center Console

• 4 hours $400 
• Half day $490
• Full day $550
• 2 days $1,050
• 3 days $1,550
• 4 days $1,950
• 5 days $2,250
• 6 days $2,500
• 7 days $2,700

Ready to book a boat rental in Anna Maria Island ? Click the button below to book a reservation or call us directly at: (941) 504-5100

2022 Tahoe T18 Boat

• Half day $350
• Full day $490
• 2 days $900
• 3 days $1300
• 4 days $1650
• 5 days $1950
• 6 days $2200
• 7 days $2300

Ready to get on the water?  Click the button below to book an Anna Maria island boat rental . or call us directly at: (941) 504-5100

2024 Seadoo GTI 130 SE

Jet Ski Rental Prices: (Up to 6 Jet skis)

• 1 hour $120
• 2 hours $220
• 3 hours $305
• 4 hours $390
• 6 hours $575
• 8 hours $650

Jet Skis will given full tank of gas during rental. Also, high end life jackets will be provided during rental.

Minimum 15% gratuity for any and all jet ski rentals.

Up to two riders per jet ski.

Ready to book a jet ski rental in Anna Maria Island ? Click the button below to book a reservation or call us directly at: (941) 504-5100

• 1 hour $240
• 2 hours $440
• 3 hours $610
• 4 hours $780
• 6 hours $1150
• 8 hours $1300

Ready to book an Anna Maria Island jet ski rental ? Click the button below to book a reservation or call us directly at: (941) 504-5100

Don't Have a License?

Boaters looking to rent a boat or a PWC (Personal Watercraft) in the state of Florida that were born in or after 1988, and who do not have a Boaters Safety Card (also generally referred to as a Lifetime Boating License), are required by law to take the Boaters Licensing Test to receive a Florida Temporary Boating Certificate. Your Temporary Certificate is valid for 90 days after completing the Boaters Test.

Boaters license are needed for all boat rentals and jet ski rental in Anna Maria Island.

Photo Gallery

Contact Seaside Island Adventures

• Tel: (941) 504-5100
• Hours: Always Open

Quicklinks:

• Call Us Today: (941) 504-5100
• Like Us On Facebook!
• Find Us on Google!
• Follow Us On Instagram!
• Privacy Policy |
• Website Accessibility Policy |
• Sitemap.xml

+1-833-779-2248

Anna Maria Island

Whether you are looking to relax, explore the bay, search for dolphins or take a dip at a sandbar, ULTRA-YACHT Charters are the perfect get away. Each charter is fully customizable to begin and end when you'd like, with multiple convenient pick-up locations.

Learn more about our charters and fleet below.

Captain & Fuel Included

All ULTRA-YACHT Charters are captained by a USCG licensed captain who will host you and operate the boat while you and your guests relax and enjoy. 

From Towels to Sunscreen on Board

Leave your worries at the dock. All ULTRA-YACHT charters are stocked with towels, sunscreen, and safety provisions. 

You Choose Your Adventure

The Sarasota Bay area offers plenty of things to do! From relaxing on sandbars to exploring islands to looking for dolphins, tell us what you'd like to do and our captains will take you there.

Relax and Enjoy the Luxuries of ULTRA-YACHT

Champagne and drinks included. Passengers are more than welcome to bring your own food or drink onboard as well, or let us take you to one the many wonderful seaside restaurants we enjoy. 

Sarasota Bay and nearby waters offer plenty of things to do! From relaxing on sandbars to exploring islands to looking for dolphins, tell us what you'd like to do and our captains will take you there.

About Anna Maria Island

Visiting Anna Maria Island and looking for things to do and places to go? Here are some our favorites!

Seafari Eco Tour From $499

Experience Florida by water on our Private Seafari Boat Tour. Enjoy a gorgeous sunset, cruise beside a pod of dolphins, learn about Florida’s sea life and other local treasures, or simply relax with a glass of champagne.

Each tour can accommodate up to 6 guests for a two hour excursion.

Gold Charter From $799

27' Formula Luxury Performance Bowrider

Ideal for open air fun in the sun. Enjoy our Bimini Top and Bluetooth Stereo with complimentary Dasani Water, Perrier, Champagne and Michelob ULTRA Beer for responsible adults.

Platinum Charter From $999

31' - 34' Sea Ray or Formula Luxury Cruiser

Outdoor fun with the added comforts of an inside cabin complete with a full bathroom, TV, refrigerator, sitting area and Bluetooth Stereo. Enjoy complimentary Dasani Water, Perrier, Champagne and Michelob ULTRA Beer for responsible adults.

Diamond Charter From $1999

44' Leopard Luxury Catamaran

All of the comforts of home including a full kitchen, three bedrooms, three bathrooms and plenty of air-conditioned space to enjoy your time on the water with friends and family. Plenty of outdoor entertaining areas to enjoy complimentary Dasani Water, Perrier, Champagne and Michelob ULTRA Beer for responsible adults.

For groups of more than 6, please contact us!

Check Availability

View a Video

Catering Options

Customize Your Cruise

Dolphin watching, an evening on the water sunset cruise, spend a night on the water, multi-day get-a-way.

Find the best Anna Maria Island boat rentals

• Boat Rentals
• • Florida Boat Rentals
• • Anna Maria Island

• Experiences
• Top locations

Boat Rentals in Anna Maria Island, FL

Rent a boat.

Click to Reserve on Boatsetter

Click to go to our rentals site

Boat rentals in anna maria island: a vacationer’s guide to sugar sand adventures.

Anna Maria Island, nestled off the coast of Florida, offers a picturesque escape for those in search of sun, surf, and sand. While the island presents various explorative avenues, opting for a boat rental in Anna Maria Island, especially with Sugar Sand Adventures, is an unmatched experience every vacationer should consider.

Why Choose our Boat Rentals in Anna Maria Island?

• Freedom to Explore: Renting a boat offers direct access to the calm blue waters that cradle Anna Maria Island. Set your own itinerary, uncovering secluded spots missed by most visitors.
• Diverse Marine Life: The surrounding waters brim with life. From dolphins that might race alongside your boat to the graceful sea turtles, every trip has the potential to become a mini marine safari.
• Breathtaking Sunsets: The sunsets of Anna Maria Island are legendary. Imagine the beauty of the sun’s descent over the horizon, best witnessed from the gentle waves on your very own boat.

Sugar Sand Adventures: The Premium Choice

Among the many boat rentals in Anna Maria Island, Sugar Sand Adventures stands out. They boast a pristine, well-maintained 2022 Tahoe Tritoon equipped with a powerful 150 horsepower motor. This modern marvel ensures a swift, stable, and secure journey across the waters.

Features of the Tahoe Tritoon:

• Performance: With its 150 horsepower motor, this boat ensures you can swiftly navigate through the waters, allowing more exploration in less time.
• Comfort: The 2022 Tahoe Tritoon isn’t just about power. Its design emphasizes passenger comfort, ensuring your time on the water is relaxing and enjoyable.
• Safety: Sugar Sand Adventures prioritizes your safety. The Tahoe Tritoon is meticulously maintained, ensuring every trip is secure.

Choosing the Right Boat Rental Service

When weighing boat rental options in Anna Maria Island, consider:

• Type & Make of Boat: Sugar Sand Adventures’ 2022 Tahoe Tritoon is a testament to the luxury and performance you should expect.
• Rental Duration: Whether it’s a few hours, a day, or more, always ensure you’re getting value for your time.
• Safety Protocols: Apart from the boat’s condition, check if life vests and safety guidelines are provided.
• Customer Feedback: Reviews offer invaluable insight. Previous customers of Sugar Sand Adventures often highlight their positive experiences, setting them apart.

Tips for an Unforgettable Boat Trip

• Carry Essentials: Water, sunscreen, snacks, a hat, and your camera should be on your list. Even in warm weather, a light jacket for the cooler sea breeze is a good idea.
• Be Eco-Conscious: Anna Maria Island’s ecosystem is delicate. Avoid littering and always keep a respectful distance from wildlife.
• Stay Informed: If you’re piloting, know the local navigation norms. The island’s surrounding waters contain sensitive areas, like seagrass beds, that must be preserved.

In Conclusion

Anna Maria Island, with its tranquil setting, is best explored from the water. And with Sugar Sand Adventures’ 2022 Tahoe Tritoon, you’re not just renting a boat; you’re guaranteeing an upscale, memorable experience. As you plan your next visit, make boat exploration with Sugar Sand Adventures a top priority and witness Anna Maria Island in its full glory.

Anna Maria Island Boat Charters

Book a day on the waters surrounding Anna Maria Island 

This page may contain affiliate links. That means if you click and buy using the link below, we may make a commission at no cost to you.

Please see my full disclosure policy for more details.

Book a Luxury Boat Charter on Anna Maria Island

Enhance your stay on Anna Maria Island by indulging in an unforgettable luxury boat charter experience. Whether you’re looking to explore the pristine waters, enjoy a sunset cruise, or spend a day fishing, our preferred providers offer a variety of options to suit your needs.

Holmes Beach, FL Luxury Charter Boat

Welcome aboard our Catamaran: the Jacqueline Noelle!

Take a cruise around the beautiful waters of Anna Maria Island. Our cruises are customizable to your interests. Your friends and family can enjoy sandbar hopping, swimming, snorkeling, or floating in pristine waters or just simply cruising the inter-coastal water way watching for dolphins, manatees, tropical birds, and other local wildlife. We offer 4-hour charters, departing at 9am and 2pm daily.

Break free from the crowds and let Jacqueline Noelle show you the best spots that Anna Maria has to offer such as Egmont Key, Passage Key, and JewFish Key to name a few. We can stop to have lunch at some of our local favorites on the water or you are more than welcome to bring your own.

Our Catamaran is conveniently docked behind the Waterline Resort in Holmes Beach on Anna Maria Island.

St. Pete FL – Luxury Charter Boat

Discover Endless Horizons with Well Played Charters in the captivating waters of St. Pete, Florida! Embark on an unforgettable journey where every moment is filled with excitement and relaxation.

Anchor at pristine beaches and dive into crystal-clear waters for a refreshing swim or snorkel. Witness breathtaking sunsets over the horizon, painting the sky in hues of orange and pink.

Whether you’re seeking adventure or simply craving a peaceful retreat, Well Played Charters has something for everyone. Book your voyage today and make memories to last a lifetime on the sparkling waters of St. Pete, FL! 

Themed Cruises:

• Sunset Cruise
• Booze Cruise
• Bachelorette Parties
• Birthday Celebrations
• Burial at Sea

Every trip is carefully designed to accommodate a range of tastes, ensuring unforgettable experiences amid stunning scenery.

Set off on an unforgettable adventure with one of AMI Rentals’ curated providers. Our private dolphin tours departing from the docks in Bradenton Beach offer an exceptional opportunity to witness these magnificent creatures up close.

Experience the enchantment of watching playful dolphins dancing in their natural habitat. Led by experienced guides aboard the Anna Maria Explorer, these daytime or sunset tours offer an unparalleled opportunity to witness these majestic creatures up close, creating cherished memories that will stay with you long after the tour.

Dolphin tours here in the bays of Anna Maria Island and Sarasota Bay are unlike any other in the world. Our Atlantic Bottlenose Dolphins are non-migratory, which means they stay here year-round and for life. On our dolphin tours, you will get to learn about these amazing creatures, our special island, the historic Cortez Fishing Village, and all the unique wildlife of the area.

Private tours take place daily with max boat capacity from 1 – 33 people.  

Locally owned and operated golf cart rentals on Anna Maria Island, Florida.

Member of Anna Maria Island Chamber of Commerce since 2022.

Quick Links

• Rentals & Pricing

Useful Links

• Blog - Meet Me on AMI
• Sunset Cruises
• Dolphin Tours
• Boat Rentals
• Fishing Charters
• Parasailing
• Baby Equipment Rentals

Legal Stuff

• Terms & Conditions
• Privacy Policy
• Disclosure Policy
• Disclaimer Policy

© 2024 AMI Rentals | All rights reserved | Site by JMAN designs

• Anna Maria Island, Florida
• Siesta Key, Florida
• Lido Key, Florida
• The Florida Keys
• South Sarasota, Florida
• Florida’s Space Coast
• Anna Maria Island Accommodations
• Anna Maria Vacations
• Exclusive AMI Collection
• Siesta Key Luxury Rental Properties
• Lido Key Vacations
• Tropical Sands Accommodations
• Bali Hai Beach Resort
• Anna Maria Island Inn
• Anna Maria Beach Resort
• Casey Key Resorts
• Coconut Cay Resort Marina
• Tropical Breeze Resort
• Melbourne Beach Resort
• Restaurants
• Experiences

Property Management

• Meet the Team
• Preferred Partners

Vacation Homes

Boutique hotels, restaurants & nighlife, exclusive experiences.

23' Pontoon Boat

Cypress Cay Tritoon

23' Starcraft SVX 231

23' Trophy Center Console

23' Bayliner Bowrider

20' Bayliner DX2000

22' Bayliner Deckboat DX2000

"Wonderful company to work with on rentals, I’ve stayed with them twice and will be back again next week!! Great communication, they have accommodated for me to get into my house prior to the regular check-in time on one situation, and have accommodated for me to check in really late as well, both with no issues whatsoever!! Well I’ll be back and stay with them, yep.. in a few days!"

"Our experience with AMI locals was great! They were very responsive and made sure we had everything we needed at the house, we hope to be back soon."

"I have rented through AMI locals 6 times. I have always been pleased with the property and with the service. We have mailed packages to their office for pick up. They have hand delivered a toaster the same day to replace a broken one. They make sure even the stupid small things don't impact your trip. Rent and relax with these people."

"We booked with AMI and had a spectacular week at Holmes beach. The house was great and enough space for my family of 5 and my dog. Everything clean and ready to enjoy. The beach just a few steps away and a wonderful pool to cool off. We will be back on the next vacation. Thank you for an unforgettable memories!!!!"

"The home we rented from AMI Locals was amazing. Check-in was easy and on time. Communication was great. I will definitely be renting one of these incredible homes again."

"Been with AMI Accommodations many times and the service is great. Just enjoyed another great vacations at Casolare, clean, comfortable and well fitted out. AMI response is great and check out super easy – would recommend."

"Anna Maria island accommodations made our first trip to AMI an incredible experience.  From start to finish they were beyond helpful and accommodating.  They gave us tips and suggestions along the way and made our stay a memorable one.  Thank you! We will be sure to visit again and use you again!"

Jennifer B.P.

"We stayed twice with Anna Maria Accommodations, just returning from our recent trip. The property was absolutely gorgeous and AMI is beautiful! We have used many vacation management companies in the past and I must say the folks at Anna Maria Accommodations are one of the best if not the best company we have ever used. They are so incredibly responsive during your stay and do everything to ensure you have the best rental experience. Thank you to the staff, you truly are amazing! We thank you and you have gained a returning client."

"AMI Accommodations homes are always well designed, nicely decorated and great vacation homes! Highly recommend"

"This is the 4th time we’ve stayed with AMI Accomodations and we always feel right at home! This current rental was just perfect for our family of three!"

"Absolutely wonderful company, we had a fantastic experience and they were always helping and responding to any questions or concerns in a very timely manner. Would highly recommend to anyone looking to stay at AMI, We will be a customer for life."

"Rental was amazing and the agency was very accommodating. Will definitely go back!"

"We had THE best experience booking & staying with Anna Maria Vacations. The website was easy to use, a representative called me a few days prior to our stay to go over some helpful details about the property, and they were in contact via text throughout our stay. There were 2 times I needed to text their concierge line and they responded super fast, and for the heating related question they had someone out in about an hour. Fantastic customer service and very very friendly!"

"Great vacation rental agency!"

"This is the 3rd time I've used them and they have given great service each time!!!"

Sunshine Living Boat Rental

Boat & jet ski rentals in anna maria island and fort myers, fl, life is better on a boat.

At Sunshine Living Rental, our goal is to make boating and Jet Skiing more accessible and affordable. Whether you’re looking for a Jet Ski rental on Anna Maria Island or a Sunshine boat rental, you’ve come to the right place. Explore ALL of Anna Maria Island and Fort Myers with us!

• Most Popular
• Tags 3 Passengers

Jetski Rentals

Enjoy beautiful Anna Maria Island and Palma Sola Bay in style with a 1-person or 2-person Jet Ski Rental! Select your hourly or half day rental and book online.

• Tags Up to 13 Passengers

Beautiful Cypress Cay Tritoon on Anna Maria Island

Enjoy the water in style! 4, 6 and 8 Hour Rentals as well as multi-day rentals available with dock or slip for the boat. Book online!

• Tags Up to 12 Passengers

23′ Starcraft SVX 231

Enjoy Anna Maria Island in style with our fantastic Starcraft 231 SVX Powerboat! It’s perfect for bigger groups that want to explore the area or hanging at a sandbar. Book online!

MORE GREAT SUNSHINE BOAT RENTALS!

Bayliner 22' dx2200 deck boat.

The new DX2200 22′ deck boat features a sleek exterior and is complete with hull sculpting and stylish shear lines while the interior is loaded with all the comforts of home.

• Tags Up to 10 Passengers

Trophy T22 Center Console

Enjoy boating around Holmes Beach, Florida and rent our Trophy Center Console for up to 10 people! Explore the sand bar, fish or just anchor and relax. Book your Sunshine boat rental online today!

• Tags Up to 9 Passengers

23′ Bayliner VR6

Enjoy a full or a half day cruising around Holmes Beach, Florida in our Bowrider boat rentals! They’re perfect to explore, swim, tube and more. Book online!

Big Grey 22’ Bayliner Deck Boat

• Tags Up to 8 Passengers
• Map Marker Fort Myers

Fort Myers 20′ 2022 Bayliner DX2000

Enjoy our beautiful new deck boat that seats up to eight people. It’s perfect for a family to lounge, fish, swim or experience a sunset cruise in Fort Myers.

WHY CHOOSE SUNSHINE LIVING BOAT RENTAL?

Sunshine Living Boat Rental is a family-owned, local business with the best prices on Anna Marie Island! We’re also proud to offer flexible hours for you to enjoy a sunset or cruise on one of our boat rentals around to the local sandbars on your own schedule. Our meeting location for all rentals is at the Kingfish Boat Ramp , located right next to the Annie Marie Island Bridge for easy access. Rent a Bowrider , Deck Boat , Pontoon boat or a Jet Ski today. Simply book your next Sunshine Jet Ski rental or boat rental online now!

ALL RENTALS FULLY INSURED

Flexible rental times, the best itinerary advice, see why people lover our sunshine boat rentals.

My family and I rented a 2022 Bayliner DX2000. What a great and smooth rental. Pick up at the docks was convenient! Martin gave excellent overview of the boat and some amazing places to go. We thoroughly enjoyed it and will be back to rent again! Highly recommended!!

We are a family of 5, so we rented 2 jetskis. We had a terrific and amazing experience. Pat was very helpful and friendly. We will definitely use them again on future trips and highly recommend them. Best rental experience and customer service we've had in a long time.

Sunshine living boat rentals are definitely a go to place for renting a boat for your adventure. Right on time for delivery and pickup. Great boat, clean and gave great instructions on all the items. Had a great day. If your ever in Anna Maria island, this is the place to rent a boat.

Exceptional service, exceptional location and they simply treated us like family. All the guys smiled and were respectful. I not only will recommend them to ALL my real estate clients but also rent jet skis again soon! Thank you for giving my son the best 25th birthday ever! You and your team totally rock!

We use cookies to improve your browsing experience.

And dolphins make us happy. Find out more about our cookies policy here .

The Best Boat Rentals in Anna Maria Island

Browse, book, and get out onto the water with local captains and boat owners., our favorite boat rentals in anna maria island.

4.9 (710 reviews)

• Boat Rentals

the United States

Anna Maria Island

Amazing 2017 Sportsman 232 Open Center Console

Captained 25' Regency Tritoon with Fuel Included

BEAUTIFUL Bennington TRITOON 150 HP Holmes Beach , Anna Maria Fishing Series

BOOK TODAY! 21ft SeaDoo Switch Sport. Fun w/family and friends.

Big Grey, our Gorgeous 23' Bayliner Deck Boat with sports tower!

Best Tahoe T18 Boat Rental In Anna Maria Island

24' Tritoon Bennington with new 175 Hp Suzuki Outboard for rent in Holmes Beach!

Captained, Anna Maria sandbars from Jewfish to clothing optional Passage Key

Bentley Pontoon Rental in Holmes Beach, Florida

Bennington Tritoon -Fishing option-Holmes Beach on Anna Maria Island

Fun and Adventure Await on a Brand-New Switch Sport!

Snorkeling, Sandbar Island Hopping, Manatees & Dolphins Tours

Suggested searches, types of boats popular in anna maria island.

Perfect for casual cruising, sandbar stops, swimming, and parties

₽5,120-₽46,070

• Fishing Charters

Let a captain do the driving while you do the fishing

₽5,300-₽69,450

Fishing Boats

Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts

₽5,300-₽73,510

Explore local waters with a boat rental dedicated to sightseeing and exploration

₽5,740-₽52,510

From mid-size to mega yachts, these luxury boats are great for groups and celebrations

₽55,160-₽106,520

Fast, fun, and easy to operate, these are a guaranteed good time on the water

₽8,380-₽42,360

Who says you need a motor to have fun on the water?

Set sail with these traditional wind-powered boats

All the comforts of home out on the water, for multi-day boat trips

Top Boat Rental Locations Near Anna Maria Island

Saint Petersburg , Florida

268 listings

Tampa Bay , Florida

231 listings

Treasure Island , Florida

142 listings

Madeira Beach , Florida

66 listings

Tierra Verde , Florida

63 listings

Sarasota , Florida

61 listings

Most Popular Pontoon Rentals in Anna Maria Island

LUXURIOUS AND SPACIOUS PARTY BOAT - BRAND NEW TRITOON

2021 New Cypress Cay 23ft Tritoon Boat for Rent in Holmes Beach!!

24' Tritoon Bennington with new 175 Hp Suzuki motor for rent in Bradenton

2021 Cypress Cay tritoon, seats up to 13ppl

Most popular fishing charters in anna maria island.

Luxury Bennington Tritoon 150HP fishing series Sx21

Nearshore Fishing Trip with Captain Alex in Bradenton

Cruise in style with this beautiful Center Console boat

"Dryft" Viking 44 Open Yacht for Charter in Anna Maria, Florida

Most popular fishing boat rentals in anna maria island.

Beautiful 25 foot Tritoon in Anna Maria, Fl available to book now

Bayliner Trophy T22 Center Console Rental in Holmes Beach, Florida

Islands, Dolphins, Sandbars and more! 6 passengers plus captain!(Fuel included)

Inshore Fishing Trip for 4 anglers in Bradenton with Captain Alex

Recent reviews in anna maria island.

This boat was exactly as listed and performed extremely well. Perfect for fishing or just enjoying the day on the water. Fit with lots of cup holders and fishing rod holders. Was perfect for our day out on the water. Will be renting again.

This 23’ bayliner is perfect for cruising the waters around here. Pick up and drop off were very simple and the boat handles the water very well. We were able to cruise along the beach down to Sarasota with no issues . Will defiantly rent again!

Truly awesome day on the water with Shawn. Great communication. Easy directions for where to meet him. Impeccable boat that was so comfortable. Cooler with ice. Comfy floats. And great recommendations for our itinerary. Definitely booking with him again next year!

Beautiful Deck Boat to Explore, Swim, Tube and more in AMI!

Meghan and her team did an awesome job! The boat was just as advertised and we had 0 issues. The gentleman that met us at the dock was very helpful with launching the boating and helping us with a small personal issue on the water. Overall great experience!

The whole rental experience was pleasant. Rich was on time with the boat at the dock he was direct with his instructions even though I have plenty of experience navigating FL waterways. The boat was clean ran well and was equipped with everything we needed! Thanks again would highly recommend.

Everything from the boat to the itinerary to Captain Shawn himself were more perfect than you could possibly imagine! He had the perfect day planned based on what we said we were looking for and he hit every mark. He made sure the kids had a day to remember and the adults got to relax! He even made sure we always had a drink in hand from the cooler we stuffed full of drinks and snacks. I cannot say enough wonderful things about Captain Shawn. He’s part of the family now and we’ll never book with anyone else. Thank you for the perfect day on the water! ❤️

Top Boat Rental Locations in the United States

Miami , Florida

933 listings

Miami Beach , Florida

439 listings

Tampa , Florida

447 listings

Los Angeles , California

405 listings

Chicago , Illinois

281 listings

Hollywood , Florida

276 listings

How To Book on Getmyboat

Find the right listing for you and your crew, with options for boat types, group size, captained or self-charter, and lots more.

Inquire & Book

Found one you like? Send a rental inquiry with your preferred trip details, and you’ll receive an offer from your captain to book.

Coordinate a pick-up place and time, meet your boat captain, and get out onto the water!

Dive into Our Journal

August 01, 2023

10 Boating Adventures of a Lifetime

Read Article

November 23, 2022

Eco-Friendly Tips for Boating Sustainably

October 03, 2022

Getmyboat's Guides to the World of Boating

April 14, 2022

The Best Meals & Snacks for a Boat Day

December 11, 2020

Tips for Boating with your Dog - Getmyboat

December 29, 2019

How to Rent a Boat with Getmyboat

Frequently asked questions.

From $70/hour. Anna Maria Island is an affordable Florida destination for a boat rental, with pontoons and small powerboats starting as cheap as $70/hour but costing about $100/hour on average. You can find larger luxury yachts for as low as $250/hour in Anna Maria Island.

With the Getmyboat app! Getmyboat is Anna Maria Island’s #1 boat rental provider, with over 50 options for rent or charter. Filter by boat type, price, and other details to find the perfect boat rental in Anna Maria Island. It’s easy, and you can do it right on your phone or on the Getmyboat website.

Yes! Anna Maria Island offers great sportfishing, pier fishing, and river fishing on the Manatee River. Book a fishing charter in Anna Maria Island and catch world-class Grouper, Snapper, Cobia, Amberjack, and the two most sought-after species, Redfish and Spotted Seatrout. A charter will provide all the bait, gear, tackle, rods, and reels you need, and pricing starts at $120/hour.

Jet ski rentals in Anna Maria Island start at $90/hour, or you can find rentals that are just $400 for a full-day rental. If you plan to enjoy jet skiing over multiple days, you can ask the owner or rental company if there are multi-day discounts available for your jet ski rental in Anna Maria Island.

• About Getmyboat
• Media Inquiries
• Terms of Use
• Privacy Policy
• Cookies Policy
• Accessibility Statement
• Member Interface Agreement
• How It Works
• Mobile Apps

Experiences

• Jet Ski Rental
• Houseboat Rental
• Pontoon Rental
• Yacht Rental
• Sailboat Rental
• Bachelorette Party Boat Rental
• Party Boat Rentals
• Company News
• Experiences Guide
• Destinations
• Tips for Renters and Owners

Popular Destinations

• Lake Lanier
• Lake Travis
• Newport Beach
• Lake Norman

24/7 Live Support

• Help & FAQs
• +1 818 927 2148
• [email protected]

Real reviews from happy Getmyboaters.

4.9 out of 5! 500,000 + reviews

• EN ES FR JA PT

Your Best Choice For Watersports Rentals

We are the only jet ski and boat rental on or around anna maria island that allows you unlimited riding without a guide in the area., jet ski rentals, center console rentals, pontoon boat rentals, tritoon boat rentals, why rent with h2o watersportz, experience the thrill.

H2O Watersportz & Reel Cortez Charters have been serving the Anna Maria Island, Longboat Key, Sarasota, Bradenton and surrounding areas since 2007. H2O Watersportz has the largest selection of fishing charters, boat & jet ski tours, boat & jet ski rentals in this region of southwest Florida.

We are located in historic Cortez, FL just over the Cortez road bridge from Holmes Beach, Bradenton Beach and Anna Maria on the island.

We are the only jet ski and boat rental on or around Anna Maria Island that allows you unlimited riding without a guide in the area. Rentals can cruise all of Tampa & Sarasota bays including along the coast of the Anna Maria Island & Longboat Key without a tour guide. We offer the only around-the-island rentals in the area!

Deep Sea & Backwater Bay Fishing Trips with Reel Cortez

Private or pay per person options, our customer reviews.

GOLD WINNER 2023 & 2024 BRADENTONS BEST BOAT RENTALS!  

   Pontoon Boat Rentals for Experienced Boaters

*Dock Delivery ~ **Flexible Rental Times ~ *** Military/First Responder Discount~

Large Boating Area ~ Multi-Day Discounts

NO BOOKING FEE!

Located on beautiful Anna Maria Island

There is nothing like being out on the water on the amazing Gulf of Mexico coast.  By renting a pontoon boat, you can experience the incredible wild life and natural beauty from a different perspective.

  There is always something wonderful to discover, from breathtaking sunsets, to dolphins playing, Anhinga's birds diving underwater, walking on white sandy beaches, anchoring off near the sandbars, wading in the aqua water, collecting shells, building sandcastles, hunting for sand dollars, to just spending quality time with family and friends. 

We are a family owned business and have lived on Anna Maria Island and in the area for over 25 years and have extensive knowledge of the area.  We are here to help you have the best experience possible.

* Dock delivery charge and gas usage apply. Not available on all weekends, Season/Spring Break or Holidays.   Subject to availability & depending on dock condition and location.   ** Flexible times subject to availability.

*** military/veteran/first responder discount offered on full day rentals and can not be combined with other discounts.  may not be available during season/spring break and holidays.     , some of the amazing experiences you see while on the water.  for more see places to visit, south anna maria island at the pass, beer can island.

  From the initial contact, to returning to the dock, we only want the best experience for our clients.  Book your rental today by calling us at  941-348-3292 .  

Your Ideal Anna Maria Island Itinerary: Making the Most of Your Vacation

Are you getting ready to visit Anna Maria Island? Make the most of it by planning a few activities and places to visit. You might not see everything in one weekend, but you’ll enjoy some of the best spots on the island. Here’s a 3-day Anna Maria Island itinerary you can try.

3-Day Anna Maria Island Itinerary

Day 1: exploring the north end.

Start your visit by deciding how you’ll get around. Renting a bike or a golf cart from one of the local rental shops is a great option. After you’ve settled into your accommodation—whether it’s a cozy rental or a pet-friendly spot—it’s time to explore.

Grab brunch or lunch at Ginny’s & Jane E’s Cafe . It’s a fun place with a laid-back vibe and good food. Afterward, head to Bean Point Beach. It’s quiet and perfect for just soaking up the sun. Check out the Anna Maria Island Historical Society Museum nearby if you’re into history.

As the day ends, walk along the Anna Maria City Pier . The sunset here is worth the wait. For dinner, try The Waterfront Restaurant . You’ll enjoy a good meal while taking in the view.

Day 2: Discovering the Heart of the Island

Kick off your day with breakfast at The Donut Experiment . You get to customize your donuts, making it a tasty start to the day.

Later in the morning, you have great options for getting out on the water. If you’re into something more relaxed, a guided kayak or paddleboard tour will let you explore the island’s wildlife up close.

If you’re up for a bit more adventure, consider taking a boat excursion to Egmont Key . This small island is great for hiking, snorkeling, and even exploring a historic fort. It’s a more active way to spend your morning and offers a different view of the area.

For lunch, head to The Sandbar Restaurant . The food is fresh, and you can’t beat the beachfront setting. After lunch, explore Pine Avenue. It’s a great spot for shopping and checking out local art.

Wrap up your day with dinner at Beach Bistro . It’s on the pricier side, but the experience is worth it.

Day 3: Adventure and Farewell

Start your last day with breakfast at Anna Maria Island Beach Cafe . Enjoy your meal right on the beach. Other early morning spots include La Crêperie and The Cheesecake Cutie & Cafe .

Spend your morning exploring more of the island. Coquina Beach is a good spot for a swim or some snorkeling.

For lunch, stop by Tide Tables Restaurant and Marina . The seafood is fresh, and the views are great.

Use your last few hours on the island to relax at the beach near where you’re staying. Let the day wind down with a final dinner. Depending on where you are, you have some good options. If you’re in Anna Maria City, try The Porch Restaurant . In Holmes Beach, The Feast Restaurant is a good option. Anna Maria Oyster Bar on the Pier is a solid choice if you’re in Bradenton Beach. Just be ready to wait for a table.

This 3-day itinerary covers some of the best of Anna Maria Island. Whether relaxing on the beach, enjoying local food, or getting out on the water, there’s something here for everyone. While you won’t see it all in one trip, you’ll leave with great memories.

Book Your Ideal Vacation Rental!

Do you need a vacation rental on Anna Maria Island? Check out the selection from Anna Maria Life Vacation Rentals . We have a range of options that will make your stay even better.

Thanks for visiting!

Popular Posts

Bradenton Beach Regulations

Trolley Stop Locations

WaterPlay USA

Start Your Vacation Now

recent posts

Anna Maria Island Bayfest 2024: Dates, Activities, and Highlights

Beaches Around Anna Maria Vacation Rentals

Browse categories.

• About the Island
• Aquariums, Museums & Zoos
• Around the Island
• Arts, Culture & Theatre
• Audiologists
• Boat Rentals | Charters
• Bradenton Beach
• Chiropractors
• Dental & Medical
• Eco-Tours | Tours
• Equipment Rental
• Fishing & Dolphin Watching
• Grooming & Pet Sitting
• Holmes Beach
• Island History
• Kid Friendly
• Local Links
• Local Services
• Nature & Wildlife
• Optometrists
• Organizations
• Paddleboarding
• Parasailing
• Pediatricians
• Pet Friendly
• Photographers
• Podiatrists
• Property Walkthrough
• Rental Management
• Restaurants
• Rules & Regulations
• Salons & Spas
• Sports & Recreation
• Spring Vacation
• Theme Parks
• Things to Do
• Transportation
• Uncategorized
• Veterinarians
• Water Sports

• Family holidays

• Dreaming of Sunset with Oliver’s Travels
• Best Cities in Europe for Remote Working 
• 10 Wow-Factor Homes For Your 2024 Reunion Holiday
• Our Top Tour De France Luxury Villas 2023
• The Most Popular Travel-Inspired Interior Trends
• The Best Places to Take a Workation – UK and Abroad
• Oliver’s Vampire Weekender – Only the Undead Should Apply!
• www.oliverstravels.com
• Smart Travel
• Places To Stay
• Travel Guides

Top 10 Things to Do in Anna Maria Island, Florida

Nestled along Florida ‘s Gulf Coast, Anna Maria Island is a hidden gem that offers the perfect blend of natural beauty, old Florida charm, and laid-back vibes. Whether you’re planning a family vacation, a romantic getaway, or a solo adventure, this seven-mile stretch of paradise has something for everyone. Here are the top 10 things to do in Anna Maria Island to make the most of your visit.

1. Relax on the Beaches

Anna Maria Island is home to some of the most pristine beaches in Florida. The powdery white sand and turquoise waters create an idyllic setting for sunbathing, swimming, and beachcombing. Head to Coquina Beach for family-friendly amenities like picnic areas and playgrounds, or visit Bean Point for a more secluded, tranquil experience. No matter which beach you choose, you’re guaranteed a stunning view of the Gulf of Mexico.

2. Explore the Island by Bike or Golf Cart

One of the best ways to explore Anna Maria Island is by bike or golf cart. The island is only seven miles long, making it easy to traverse. Many local shops offer rentals, and you’ll find designated bike paths throughout the area. As you ride, you’ll discover charming neighbourhoods, scenic views, and hidden gems like local boutiques and cafes.

3. Visit the Historic Anna Maria City Pier

The Anna Maria City Pier , originally built in 1911, is a must-visit spot on the island. It offers spectacular views of Tampa Bay and is a great place for fishing. Whether you’re an experienced angler or just looking to relax, you can rent fishing gear on-site. The pier also hosts a restaurant where you can enjoy fresh seafood while taking in the panoramic views.

4. Kayak or Paddleboard in the Mangroves

For a unique way to experience Anna Maria Island’s natural beauty, rent a kayak or paddleboard and explore the surrounding mangroves and waterways. The calm, shallow waters are perfect for beginners, and you’ll likely encounter local wildlife such as dolphins, manatees, and various bird species. Robinson Preserve and Bimini Bay are popular spots for these activities.

5. Shop at Pine Avenue

Pine Avenue, often referred to as the “Greenest Little Main Street in America,” is the heart of Anna Maria Island. This charming street is lined with locally owned boutiques, art galleries, and speciality shops. Whether you’re looking for a unique souvenir, handmade jewellery, or coastal home decor, you’ll find it here. Don’t forget to stop by one of the local bakeries or cafes for a treat.

6. Dine at Waterfront Restaurants

Anna Maria Island boasts a variety of waterfront dining options that cater to all tastes. From casual beachside cafes to upscale restaurants, you’ll enjoy fresh, local seafood while watching the sunset over the Gulf. The Sandbar Restaurant is a popular choice for its toes-in-the-sand dining experience, while The Waterfront Restaurant offers a more refined atmosphere with stunning views of the bay.

7. Take a Sunset Cruise

One of the most unforgettable experiences on Anna Maria Island is a sunset cruise. Several local companies offer boat tours that take you out on the Gulf of Mexico, where you can watch the sun dip below the horizon in a blaze of colour. Many cruises also include the chance to spot dolphins and other marine life. It’s a perfect way to end a day on the island.

8. Visit the Anna Maria Island Historical Museum

To learn more about the island’s rich history, pay a visit to the Anna Maria Island Historical Museum . Housed in an old icehouse, the museum features exhibits on the island’s early settlers, its fishing heritage, and the development of the island over the years. The museum also offers walking tours that highlight historic sites and landmarks.

9. Explore Egmont Key State Park

Just a short boat ride from Anna Maria Island, Egmont Key State Park is a pristine natural sanctuary that’s worth the trip. The park is home to historic ruins, a working lighthouse, and a variety of wildlife. You can spend the day exploring the island’s trails, snorkelling in the crystal-clear waters, or simply relaxing on its unspoiled beaches.

10. Attend Local Events and Festivals

Anna Maria Island hosts a variety of events and festivals throughout the year that celebrate its culture and community spirit. The Anna Maria Island Art League hosts annual art festivals showcasing local artists, while the Food and Wine on Pine event offers a taste of the island’s culinary scene. Check the local event calendar during your visit to see what’s happening.

Whether you’re drawn to the island’s beautiful beaches, historic charm, or outdoor adventures, there are things to do in Anna Maria Island for every visitor. With its relaxed pace of life and breathtaking scenery, it’s no wonder this slice of paradise has become a favourite destination for travellers from around the world. So, pack your bags, put on your sunscreen, and get ready to discover all the incredible things to do on Anna Maria Island, Florida.

That’s our roundup of the best things to do in Anna Maria Island – what will you do first? Check out our gorgeous homes for rent in Anna Maria Island and see what else we have in Florida too. Make sure to explore the whole portfolio of homes around the world on Oliver’s Travels and contact our friendly concierge team to learn about all the fabulous extra services we can book for you!

Leave a Reply Cancel Reply

Your email address will not be published.

Our Reservation Specialists are available 9 AM-Midnight EST, 7 days a week

• Name * First
• Sign Up For Email Updates
• Comments This field is for validation purposes and should be left unchanged.

Anna Maria Island Villa Rentals

Book our anna maria island villa rentals below.

Compare Properties

--> --> = 2"> Compare Now = 2" ng-click="clearCompare()" ng-bind="'Clear Compare list'">

Unable to find any listings.

Property Inquiry

Luxury and comfort, privacy and exclusivity, personalized experience, home-like amenities, proximity to the beach, family and group-friendly, seabreeze vacation: your premier choice, extensive selection of properties, local expertise and personalized service, quality and comfort, convenient booking process, commitment to guest satisfaction, planning your stay on anna maria island.

• Book in Advance: Anna Maria Island is a popular destination, and villa rentals can fill up quickly, especially during peak seasons. To secure the best property and rates, it’s advisable to book your villa well in advance.
• Consider Your Preferences: Think about your preferences and requirements when selecting a villa rental. Consider factors such as proximity to the beach, the size of the property, and the amenities you desire. SeaBreeze Vacation can help you find a villa that meets your specific needs.
• Plan Activities: While relaxing in your villa with a private hot tub is a highlight, Anna Maria Island offers a range of activities and attractions to explore. Plan your itinerary to include beach outings, dining at local restaurants, and visiting popular spots such as the Anna Maria Island Pier and the Robinson Preserve.
• Pack Accordingly: Florida’s weather can vary, so be sure to pack accordingly for your trip. Lightweight, breathable clothing is ideal for warm weather, while a light jacket may be useful for cooler evenings.

Book Your Anna Maria Island Villa

DOT repairs hole, reopens AMI Bridge overnight

Temporary injunction against kayak tours denied

Prize-winning print

Cortez boat rescues spark scrutiny of on-the-water rentals

Island news brings us together

Subscribe for unlimited digital access to the news that matters to your community.

#AMITOGETHER

by Robert Anderson | Be the first to comment

A short-term rental business operating out of Cortez is under scrutiny after multiple rescues of customers raised safety concerns.

U.S. Coast Guard Sector St. Pete confirmed Aug. 27 that over eight months it responded to eight distress calls from people renting vessels from a company known as EbbandFlow Marina LLC.

According to the EbbandFlow Facebook page, the company, owned by Brittany Bull, offers short-term rentals aboard a fleet of sailboats anchored in an area referred to as Sailors Park in the waters of Sarasota Bay near Cortez.

Recent reports suggest the company’s operations may not be as easygoing as the locale where customers are vacationing.

“Coast Guard Station Cortez has had to go out and rescue people from the vessels that are outside of Station Cortez,” public information officer Santiago Gomez told The Islander in an Aug. 29 interview. “We have had to rescue people off of them.”

Santiago also said this was not the only issue the Coast Guard has had with Bull this year.

“U.S. Coast Guard Sector St. Pete is currently investigating a possible violation of a captain of the port order that Brittany Bull was involved in,” Gomez said. He did not elaborate on the open investigation.

One of Bull’s short-term rental tenants, Harry Hibler of Ohio, said he and his wife, Tatyana, made arrangements in January to stay aboard one of the vessels at Sailors Park.

“We booked a week on a sailboat in Sarasota, Florida,” Hibler wrote to The Islander in an Aug. 30 email. “We paid the full amount in advance.”

Hibler said he and his wife drove from Ohio to Florida and arrived at the location at the correct time but no one was there to greet them and take them to a boat.

“I called and texted the host who said she would meet us there,” Hibler said, referring to Bull. “She said that she had to be out of town for an unexpected event. She said someone else would take us out in the water to the boat later. We waited an hour and a half. It was getting dark. My wife was feeling unsafe.”

Hibler said after waiting several hours they never made it out to the vessel and left the area, opting to travel to Orlando and stay in a hotel.

“We found this business through Airbnb,” he said referring to Bull’s rental. “However, when I contacted the host thru Airbnb she asked me to phone her and pay by credit card over the phone. When that did not work, she asked me to pay through PayPal. I did not realize that this transaction was taking place outside of Airbnb. When I reported the situation to Airbnb, they told me that they could not help me because the transaction had not gone through them. When the host requested that I pay through PayPal she insisted that I use the ‘friends and family’ option.”

Hibler later learned that the “friends and family” option on PayPal offers no buyer protection, making a dispute of the charges almost impossible.

Hibler said he reported the incident to the Ohio Attorney General’s office, the Federal Bureau of Investigation and the Manatee County Sheriff’s Office.

He said the matter is under investigation.

Meanwhile, local captains and business owners who operate in the vicinity of Bull’s vessels, located a few hundred yards from Coast Guard Station Cortez, 4530 124th St. Court W., also are voicing concerns.

Karen Bell, owner of AP Bell Fish & Co. and Star Fish Co. in Cortez, said she contacted the MCSO to prevent Bull from using her business docks to pick up guests and ferry them to the vessels.

“I had her trespassed from the Starfish, Fullford, A.P. Bell and Florida Institute for Saltwater Heritage docks,” Bell said.

Once on the vessels, some people have been left without a way back to shore, Bell added.

“We kept finding these people who couldn’t get back off the boat and so they’d be screaming to our fishermen, asking could someone come help them?” she said.

Capt. Katie Tupin, who runs Captain Katie Scarlet Boat Tours out of Cortez, said she and her mother, Capt. Kathe Fannon, also a tour boat operator, have seen several Coast Guard rescues.

“I’ve seen the Coast Guard out there at least five times,” Tupin said Aug. 29. “Mom has helped at least two individual people back to the dock.”

She said many of the boats in Bull’s fleet were once sunken or derelict vessels that Bull salvaged and cleaned up.

However, many of them still are not seaworthy, said Tupin.

Bradenton Beach police Officer Eric Hill, who heads the city’s derelict vessel removal program, spoke with The Islander Aug. 29 and said law enforcement agencies are scrutinizing Bull’s vessels.

While Hill abides Bradenton Beach’s jurisdiction across the Intracoastal Waterway, he said during interagency meetings, Bull’s business has been discussed.

“We’re all looking at her for the simple fact that she’s doing stuff that’s not lawful,” he said.

Hill recounted observing Bull tow a vessel out of Cortez to a sand flat in the ICW east of the Coquina North Boat Ramp, just outside BBPD’s marine patrol jurisdiction.

When Hill confronted Bull about dumping the vessel she said the boat was hers but that it would not come back as registered to her name. She said she would remove the vessel in a few weeks.

Hill said he informed the MCSO as to the boat’s location and owner for further investigation.

Typically, derelict and abandoned vessel issues are handled by the Florida Fish and Wildlife Conservation Commission, which works in conjunction with county and municipal law enforcement agencies to remove them.

Florida law defines “derelict vessels” as those left in a wrecked, junked or substantially dismantled condition on public waters. Vessels can become derelict due to neglect, abandonment or because of a natural disaster.

The vessels, whether sinking, aground or lacking vital operational systems, create hazards in the waterways.

Derelict vessels pose risks to boaters, wildlife and natural resources.

The Islander reached out to Bull by email Aug. 29 and by phone Aug. 30 but as of Islander press time Sept. 2 there was no reply.

The Islander reached out the FWC for information related to EbbFlow’s operation in Sarasota Bay but as of Islander press time Sept. 2 there was no reply.

More from The Islander

Leave a Reply Cancel reply

You must be logged in to post a comment.

The Anna Maria Islander 315 58th St., Suite J, Holmes Beach FL 34217

Phone: (941) 778-7978 Fax: (941) 778-9392

For general information: [email protected]

Site design & maintained by Wayne Ansell

Islander News

• Classifieds
• Place a Classified Ad
• Real Estate

Other Links

Subscribe to news alerts.

Email address:

Sign up to receive FREE email alerts when we update our site with news and classfieds.

Social Media