Things to Do on Anna Maria Island, Florida: Experience Old Florida Charm on the Gulf Coast

Anna Maria Island is a small, eleven kilometre long island on Florida’s Gulf Coast filled with exciting things to do. It’s an incredible beach destination filled with opportunities to relax, get out on the water and enjoy its delicious restaurant and bar scene.

With each trip I take to Florida, I’m surprised by how diverse and varied it is. From Jacksonville to Miami, each part of the state has its own unique history and culture. The region of Bradenton and Anna Maria Island has been especially important to my family for generations, so this return trip to Anna Maria Island felt like a homecoming in a lot of ways.

It was fun to bring Chris to a place that was so special to me in my childhood, and experience it in a whole new light on our couples’ getaway. Anna Maria Island exudes that slow-paced, Old Florida charm that feels more difficult to find with each passing year. The beaches are warm and inviting, the preferred methods of transportation are golf carts and bikes, and there are plenty of afternoons spent with a good book or enjoying a happy hour with friends here. And we can’t forget how magical the sunsets are, too.

We loved our couples’ getaway to Anna Maria Island, and whether you’re planning for a romantic getaway or a family or friends’ getaway, you’ll find that so much of this island can be enjoyed by any type of traveller. Let me help you plan for the best trip here!

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How to Get to Anna Maria & How to Get Around

If you’re coming from further away, the closest airport to the island is Tampa International Airport. From here, it’s about an hour and a half to drive. Renting a car is a great option if you want to visit more places in and around the Tampa Bay and Bradenton areas during your trip, but you don’t actually need a car if you plan on spending most of your time on Anna Maria Island.

Without a car, you can arrange for a shuttle from Tampa International Airport to the island—check with your hotel to see about the best options for your trip. Once you’re on the island, the Island Trolley is a free shuttle that runs the length of Anna Maria Island every twenty minutes or so. This is such a convenient way to get around the island, since the island itself is long and narrow, so it’s easy to walk from each of the shuttle stops to your destination.

You can also arrange for bike or golf cart rentals to get around the island, if you’re looking for something between walking and getting a shuttle, but still looking for something other than a car. Visiting without a car on the island is a great alternative, since there can be traffic leaving and coming onto the island at different times of day, so this is a nice way to not have to worry.

The Anna Maria Island Ferry is another great alternative to using a car, which connects Anna Maria Island to Downtown Bradenton. We used the ferry to get to Bradenton on the day we explored downtown, which was a nice way to get out on the water and see the island, Palma Sola Bay and the Manatee River from the water.

Stay at an Independently Owned Hotel, Like Silver Surf Beach Resort

There are some pretty incredible accommodations on Anna Maria Island that will feel like your home away from home. Silver Surf Beach Resort is one of those places. It’s independently owned with its own private beach directly across the street. The staff is friendly, there’s a pool on the property, and a grab-and-go breakfast is available to all guests during your stay.

Chris and I loved waking up and having a coffee on the porch before we decided what we were going to get up to each day. I loved how the rooms have ample storage and closet space, plus several of the rooms can sleep up to four guests thanks to their pull-out couches, which makes this the perfect set-up for a family or friends’ getaway.

Silver Surf even has communal BBQs and a picnic area near the beach, and a full-sized fridge and kitchenette in their rooms, making it the perfect place to feel like you’ve got your own private apartment right on the island. There’s also an Island Trolley stop right outside of the hotel, easily connecting you to any part of the island during your stay.

If Silver Surf is sold out during the time of your visit, there are many other accommodations on the island. You can feel free to use this map to help you find the best one for your trip.

Things to Do on Anna Maria Island, Florida

Anna Maria Island is, first and foremost, a beach destination. With over 11km of beach stretching along its west-facing coast on the Gulf of Mexico, you can enjoy long, sunny days by the water during so much of your trip. If you stay at a hotel like Silver Surf with a private beach, the access to umbrellas and sun chairs makes beach days an absolute breeze, and you’ll be thankful for a little reprieve under those umbrellas on the sunniest of days!

Well known beaches on the island include Holmes Beach, Bradenton Beach and Anna Maria Island Beach. One of my personal favourite spots is Coquina Beach near the south of the island, but you really can’t go wrong when so much of the island is beach-focused.

Of course, if you’re looking for other amazing things to do on the island, there is no shortage of fun things to get up to!

Take a Tour with Anna Maria Island Dolphin Tours

We absolutely loved our tour with Anna Maria Island Dolphin Tours. They run all sorts of tours, but we took a Sunset Dolphin Tour and it was quite possibly one of the most memorable experiences on our trip. Not only was our guide, Chris, so knowledgeable about the local dolphin population and their routines, but it was clear that being from the area he had a serious passion for being on these tours and experiencing the connection with marine life right alongside his guests.

We ended up seeing two dolphins who were likely a mother and her child, and Chris expertly stayed a safe and responsible distance from them. He had a feeling that if he started to speed up a little, they might decide to ride our wave—and that’s exactly what they did! It was honestly a magical experience, and I can safely say I’ve never been trailed by a pair of dolphins for that long. It was a good feeling to know that they decided to join in, too—Chris was very firm on letting the dolphins take the lead, which should always be the case on wildlife tours.

We wrapped up the tour watching the sunset over the Gulf of Mexico. This was a fantastic way to feel more connected to the island from the water, and if you’re looking to take a memorable tour during your trip, I’d highly recommend booking this one.

Learn a Little About the Island and Region’s History

In its earliest histories and for the longest stretch of time, the island now known as Anna Maria belonged to the Indigenous Manasota peoples. They practiced what is known as Safety Harbor Culture, where burial mounds filled with ceramics made up the centre of their societies. For a more in-depth look at this history, The Bishop Museum of Science and Nature in Downtown Bradenton is an excellent place to visit.

Spanish expeditions began to pass through the area by the 1500s, and by the 1800s the first Europeans began to settle on Anna Maria Island. Up until the early 1920s, the island was inaccessible by car, but once bridges were built it significantly increased tourism and the number of inhabitants on the island.

Today, historic Pine Avenue has some of the oldest buildings that still remain on the island, including The Island Players theatre at Gulf Drive and Pine Ave. It’s worth walking along this street not only to go shopping, but to visit some of its historic buildings. Don’t forget to stop in at the Anna Maria Island Historical Society while you’re in the area, too.

Historic Bridge Street is another great area to walk around and get a sense for some of the “Old Florida” buildings on the island.

Take a Long Walk

anna maria island things to do — Chris and I walking on beautifully protected boardwalks on Coquina Beach

On a breezy, sunny day there’s nothing I love more than to stretch my legs and take a break from lying on the beach for a long walk. You could really walk more or less the whole length of the island along the beach if you’d like, but if you prefer paved or flat walking areas, you can walk along the shoulder of the island’s main road, Gulf Drive. Walking around the island early on in your trip is a great way to scope out cute shops, restaurants and cafes that you might want to visit during your time on the island.

I’m happy to say that I felt like the cars were considerate of pedestrians walking along the road on the island, including stopping to let us cross. There are also some nice stretches of protected boardwalks and walking paths separated from the road closer to Coquina Beach.

InDulge in the Restaurant and Bar Scene

Whether you’re spending your whole trip on AMI, or you plan on venturing to some nearby spots, there are some truly wonderful places to go for a nice lunch or dinner in the area.

One of Chris’s and my absolute favourites was The Doctor’s Office. It’s located close to Keyes Marina, more or less in the middle of the island near Holmes Boulevard and Gulf Drive. Owned by a Nova Scotian and located in what used to be an actual doctor’s office here on the island, this restaurant serves up incredible cocktails and dishes with a serious commitment to the doctor bit. Relics of the original doctor’s office like weight scales and model skeletons decorate parts of this quirky, upscale bar, and all visitors are served a “wellness shot” on arrival—doctor’s orders!

On top of a truly hilarious commitment to the bit at The Doctor’s Office, it’s hard to say whether the cocktails or the dinner menu items stand out the most—there really isn’t a weak link here. I’d recommend sitting at the bar for a fun date night to watch all of the expertly crafted cocktails come together. Chris and I loved our respective Old Fashioned and Mai Tai, and their World’s Best Smoked Salmon and Lobstercargots make for incredible starters. Keep an eye out for their daily specials, too.

Sandbar Seafood + Spirits is another great place to head for drinks, a date night or an evening out with a larger group on AMI. I’d recommend arriving before sundown, so you can watch sunset from their patio over Anna Maria Island Beach and the Gulf of Mexico. Their bar serves up all sorts of mixed drinks, wine and beer, and they have chairs and corn hole toss set up on the beach and if you’re looking for a good place to park yourself as you wait for your table. Their classic pub fare and seafood menu offers something everyone in your party will be happy with.

If you plan on venturing outside of Anna Maria Island, here are a few more places I’d highly recommend checking out:

Taverna Toscana: This incredible restaurant is located in downtown Bradenton and serves up Italian dishes with a Florida flare. Expect a warm and inviting ambiance, a fantastic wine selection and absolute perfection from the beginning to the end of your meal.
Oak & Stone: This is a great place to come for lunch or a beer tasting in downtown Bradenton. With 50 rotating craft beers available to try on their self-serve tap wall, it’s a memorable place to come for a beer lover.
Shore LBK: This open- air restaurant just south of AMI on Longboat Key serves up delicious cocktails in a wonderfully relaxing and elevated environment. Their Key West shrimp and Scallop Risotto are fan favourites.

Get Out on the Water

Getting out on the water is a fun way to see the island. On top of the Dolphin Tour mentioned above, you can take the Gulf Islands Ferry from Bridge Street to Downtown Bradenton, which offers great views of Palma Sola Bay and the areas east of the island—keep an eye out for dolphins as you go.

Anna Maria Island is also the perfect place to enjoy water sports. Right outside of Silver Surf Beach Resort there is an outpost for rentals like sailboats and stand up paddle boards, and from our private beach we could see groups taking a parasailing tour on the Gulf shore.

Hit the Shops of Pine Avenue

If you love to shop or just enjoy popping into stores during your travels, there are a few spots on the island that are great to do this, but Pine Avenue is a favourite. On top of being an historic centre of the island, there are some wonderful cafes, shops and restaurants to stop in at here.

Start at North Shore Cafe. It’s a great place to grab a coffee or a sweet treat for early in the day. You can sit on their beautiful back patio area overlooking the lagoon—don’t forget to snap a photo of their vibrant “Anna Maria” mural—or pop into their shop for unique beach accessories and t-shirts.

From there, continue east all the way down to the AMI City Pier. There are plenty of wonderful shops, restaurants and boutiques to stop at on this stretch of the island, and you’ll be hard pressed to not walk away with something special. Anna Maria General Store, Shiny Fish Emporium and The Island Cabana are all worth popping into. Unfortunately, recent hurricanes took out the AMI City Pier boardwalk, but you can still walk to the edge of the water to take a look at the pier from the island.

If you’re looking for another nice place to walk around and do a little shopping, Historic Bridge Street is a good place to come. There are a few restaurants and bars in the area with live music throughout the week, and the Fudge Factory is a favourite place to come for fudge and ice cream.

Catch a Sunset

Anna Maria Island is famous for its sunsets, and with west-facing beaches running practically the whole stretch of the island, it’s no wonder why. Bean Point is the northernmost part of the island, and a favorite for sunsets because of its clear views over the Gulf of Mexico. We also loved watching the sunset from Anna Maria Island Beach, and were even surprised to find intricate sand castles created by local artist Pete the Sandman scattered along the beach. They looked amazing as the daylight turned to night.

But of course, no matter where you are along the Gulf of Mexico, you’ll catch a view of a beautiful sunset. As much as the location matters when it comes to sunset views, it’s really the people you’re able to spent sunset with that make the views all the more memorable for long after your trip comes to an end.

Don’t Forget to Visit Nearby Bradenton!

As much as there is to do on AMI, it’s definitely worth heading over to nearby Bradenton for a half- or full day trip. I’d highly recommend taking the Gulf Islands Ferry from the Historic Bridge Street Pier to Downtown Bradenton’s Riverwalk. It runs Wednesdays to Sundays, and is an excellent way to leave the car behind and get out on the water.

While you’re in Bradenton, walk along the Riverwalk before stopping for lunch at Oak & Stone on the water. On a sunny day without much wind, the views from their rooftop space are beautiful. Afterwards, you can spend some time walking along historic 12th Street and head over to The Bishop Museum of Science and Nature. Dinner at Taverna Toscana after a day well spent in Bradenton is a must.

If you have a vehicle, or if you’re looking to a do a little more while you’re in town, the Robinson Preserve is a beautiful place to go for a walk on one of their trails or take a kayaking tour. Bradenton is also the home base for the Pittsburgh Pirates’ Spring Training in the Grapefruit League. The season runs from late February to late March each year.

I’d like to thank Bradenton Gulf Island Tourism for hosting Chris and I as media during this trip. All opinions expressed are completely my own.

Bri Mitchell

Bri Mitchell is a travel writer and content creator from Toronto, Ontario. She loves to highlight all things nature, food, wellness, sustainability and adventure in her work. Bri writes and shares her travel experiences from across Canada, the United States and around the world on Instagram and TikTok (@brimitchelltravels), and in her articles for travelingmitch, Ultimate Ontario, and We Explore Canada.