Fun Things to Do on Anna Maria Island, Florida

Beaches in Sarasota, Florida

Fun Things to Do on Anna Maria Island

Since visiting Sarasota for many years and now living here, we have started spending more time exploring nearby spots and revisiting our favorites such as Anna Maria Island. In this Florida travel guide, we’ll cover a number of things to do on Anna Maria Island, places to eat, and of course, the best beaches. But first… a bit of history!

Anna Maria Island received its name from Madison Post, a former mayor of Tampa who decided to name the island after his sister-in-law Anna and his wife Maria. But before Anna Maria Island was named it was originally native land belonging to the Tocobaga, Seminole, and Calusa tribes until around 1539 when Spanish explorers including Hernando de Soto began to colonize the area.

Although many people had visited and stayed on the island temporarily, George Emerson Bean became the first permanent resident in 1892. He set up his home on what is known today as Bean Point and lived there until he passed in 1898. After his death, his son George Wilhelm Bean partnered with Charles Roser to further develop the island. Together they created the Anna Maria Beach Company which paved the path for new residents on the island.

Interesting fact, Roser was also credited as the creator of the Fig Newton which made him most of his fortune that he used to invest in Florida real estate. 

As they continued to develop the island, more and more people flocked to the area, especially after the first bridge was built in 1922 that connected Anna Maria Island to the mainland of Florida. Today, Anna Maria Island is home to around 8,500 residents. The Bradenton area, which connects to Anna Maria Island, sees about 3.2 million visitors each year. Now let’s dive in on the many things to do on Anna Maria Island.

Disclaimer: This post contains affiliate links from which we may make commission from. As always, we only recommend places and products we love! In addition, we try our best to keep our articles up-to-date with current prices, locations, and hours of operation however we always recommend double-checking when planning a trip as these items can change frequently.

Where to Stay on Anna Maria Island

Because Anna Maria is relatively small there aren’t as many hotels and places to stay on Anna Maria Island as you’d find in Sarasota or Bradenton, but there are a few places that we’d recommend if you want to stay on the island.

The Waterline Marina Resort & Beach Club has luxurious two-bedroom condos with ocean views, an onsite restaurant, and a number of water spot amenities to enjoy. Another great feature is that they have bicycles available for use making it easy to get from place to place on the island.

A recent addition to Anna Maria Island is Joie Inn. Joie Inn is a small boutique hotel with four different rooms to choose from that can accommodate 2-5 people. Although small, Joie Inn comes with a number of amenities such as a heated pool, e-bikes available for use, and chairs, a wagon, towels, and an umbrella to use on the beach. In fact, Joie Inn is just one block from Holmes Beach making it very accessible!

Another option for staying on Anna Maria Island is renting a home or condo through VRBO or Airbnb. Here’s the thing, I have mixed feelings about homeshare properties because while they can be more affordable and host more people, a lot of times, especially in touristy areas, they take away housing and drive up prices for people who live in the area full-time. However, I do love having a space to cook and feel at home for a week+ trip.

Look for more places to stay on Anna Maria Island

How to Get Around Anna Maria Island

Although we’ve driven to Anna Maria Island from Sarasota it can prove pretty challenging especially in peak season because of traffic and lack of parking. Here are some alternate ways to enjoy the island that are low-cost or completely free!

Anna Maria Island Free Trolley

Typically the trolley starts at 6am from both ends of the loop and runs in 20-minute intervals until 9pm and then every 30 minutes until 10:30pm. The 35 northbound and southbound trolley stops are located every 2-4 blocks on the island so you should never be far from one at any given time. Although you can find the timetables and stops on the MCAT site, the easiest way to check the trolley schedule and stops is to download the myStop app.

In addition to the Island Trolley, there is also a newer trolley called the Beach ConneXion Shuttle which runs every 20 minutes from December-April each year from 10am-6pm and stops at beach access points. Like the island trolley, you can find information about Beach ConneXion Shuttle schedules and stops on the myStop app. 

Biking Around Anna Maria Island

Another way to enjoy the sights at Anna Maria Island is to rent a bike. Anna Maria Island is extremely accessible by bicycle and there are a lot of paved biking paths you can ride on in nearby Bradenton and Sarasota if you want to go for a longer ride. 

Rent A Golf Cart

If you are staying on the island you might also consider renting a golf cart for the duration of your stay. Not only is this an easy way to get around the island, it’s also perfectly acceptable on many parts of the island. 

READ MORE: Things to Do in Sarasota, Florida

Things to Do on Anna Maria Island

Despite its size, Anna Maria Island boasts a number of unique things to do and it’s a great place to visit for a day trip from Sarasota or Bradenton or you could spend a week there if you’re someone who wants to just relax. Here are our favorite things to do on Anna Maria Island.

Visit Bayfront Park

Bayfront Park is located on the northernmost point of Anna Maria Island and has a number of amenities perfect for gatherings for friends and families. There are picnic tables, charcoal grills, restrooms and showers, and a playground available for public use. 

In addition, there are some areas of beach access as well! While we haven’t spent a lot of time at Bayfront Park when it’s just the two of us, it’s great for gatherings with friends, families, and especially families with kids because of the playground. 

In addition, Bayfront Park is a great picnic spot and is a well-known fishing spot that’s great for younger anglers or those who want to do more leisurely fishing. 

Location: 316 N Bay Blvd, Anna Maria // MAP

Check-out the Public Beaches on Anna Maria Island

Beaches in Sarasota, Florida

Anna Maria Island has some of the prettiest beaches in the Sarasota area with ample amenities and easy access via the free trolley system on Anna Maria Island. 

  • Bean Point Beach is located at the very tippy top of Anna Maria Island and has beautiful white sand and epic sunsets. // MAP
  • Coquina Beach is by far one of our most favorite beaches in Manatee and Sarasota Counties that I honestly hesitate to tell you about it. It is located towards the south of the island and has a number of amenities like sand volleyball, concessions, and ample parking (currently under construction to create better spaces). // MAP
  • Manatee Beach is located in the center of the island and like the others has pretty white sand beaches and many family-friendly amenities // MAP

Go Shopping on Pine Avenue

Containers of olive oil at Olive Oil Outpost on Anna Maria Island

Pine Avenue is probably the most popular spot on Anna Maria Island because of its abundance of local stores and restaurants and proximity to other popular things to do on Anna Maria Island. Pine Avenue is also within walking distance from Bayfront Park and the Anna Maria Island City Pier making it more accessible without driving. 

Here are a few stores to check out on Pine Avenue:

  • Olive Oil Outpost is a gourmet grocery store that has olive oil, balsamic vinegars, cheeses, and other items. They even have free olive oil and balsamic tastings.
  • Anna Maria General Store: This is a great shop to grab some items for a picnic at Bayfront Park.
  • Shiny Fish Emporium is a cute 1950’s beachy themed store that has an array of items to peruse including confections, crafts, toys, and home goods. 

Location: Pine Avenue, Anna Maria // MAP

Stop By the Anna Maria City Jail & Historical Museum

Outside of the old jail at Anna Maria Island

Also on Pine Avenue, you’ll find the Anna Maria Historical Society Museum, which is located in the old island ice house. This museum offers a glimpse of the history of Anna Maria Island and the first homesteaders, George Emerson Bean and Charles Roser, famous for their creation of the Fig Newton.

While today the next-door Anna Maria City Jail is a fun photo spot it was built in 1927 and was once used to detain local troublemakers. The jail was originally built without windows and filled quickly with mosquitos making the conditions at the jail less than optimal and the fear of that keeping crime at bay. The jail was used until 1940 when a fire broke out and burned part of the jail but the concrete structure remains today with quirky slogans painted on the front.

If you’re interested in learning more about the history of Anna Maria Island, definitely don’t miss this small museum.

Location: 402 Pine Ave, Anna Maria // MAP
Hours: January-March: 10am-4pm, April-December 10am-1pm

Book A Kayak, Canoe, or Water Sport Rental

Kayaking in Sarasota

There are a number of great kayaking spots to enjoy in the Anna Maria Island area including mangrove tunnels, Tampa Bay, or a nearby nature preserve. If you haven’t kayaked in this area or ever kayaked before I recommend trying a guided tour which will provide you with information about the area as well as show you a leisurely route to take. However, if you aren’t a novice kayaker or you want to rent a kayak to take your own route many rental companies will provide you with maps for routes to take or you can find some on apps like Strava or AllTrails. 

Here are a few rental companies for kayaks, canoes, and other water sport activities:

  • Lazy Turtle Beach Rentals: Bicycle rentals, beach rentals, surf/bodyboard rentals, kayaks and canoes, kayak tours, fishing gear, and scooters. // MAP
  • Beach Bum Recreational Rentals: Kayak rentals and tours, paddleboards, beach rentals, bicycle rentals, and golf cart rentals. // MAP
  • Kayak Jacks: Kayak rentals and tours. // MAP

Take A Walk Down the Anna Maria Island Pier

View of the Anna Maria Island Pier

When the Anna Maria Island Pier first opened it was used to bring daytrippers that came by steam boat from St. Petersburg and the mainland of Florida, keep in mind this was before there were bridges to the island. While there isn’t that much to do here, you can stroll down the pier while eating an ice cream cone, go fishing, grab dinner at the Rod & Reel Pier restaurant, gaze at the water and wildlife, or watch the sunset! Personally I love walking down the pier because the water is so pretty to look at.

Location: 875 N Shore Dr, Anna Maria // MAP

Enjoy A Leisurely Walk Around Leffis Key Preserve

Entrance to Leffis Key Preserve on Anna Maria Island

Since Florida is a mostly flat state, and by mostly I mean the highest point of elevation is 345 feet, all of the hikes are relatively easy. Leffis Key Preserve is a small preserve with shelly trails and boardwalks that is great for any time of the day. One unique feature of Leffis Key is the 26-foot hill that is centered in the preserve. From the top, you can enjoy a beautiful 360-degree view of the Gulf of Mexico and Sarasota Bay.

Location: Near 1427 Gulf Dr S, Bradenton Beach // MAP

Grab An Ice Cream Cone at Two Scoops

Two scoops of ice cream from Island Scoops in Anna Maria Island

I like to consider myself an ice cream connoisseur. I mean I have written about the many flavors of ice cream I’ve had in Japan and I also tend to write about my favorite ice cream shops in every city I’ve lived in, including this one about my favorite ice cream in the Sarasota area. Two Scoops is a classic ice cream shop that has all of the classic favorite scoop ice cream flavors plus some Floridian flavors like gator tracks, toasted coconut, and orange pineapple. I recommend grabbing a cone of your flavor of choice and taking a walk down the Anna Maria Island Pier.

Location: 101 N Bay Blvd, Anna Maria // MAP

Get A Drink at The Doctor’s Office

Cocktails from The Doctor's Office on Anna Maria Island

It’s time to fill your prescriptionat The Doctor’s Office! Well, your liquid prescription that is. While at first, you might think that this is just a bar with a quirky name it’s actually called the Doctor’s Office because the space this swanky cocktail bar resides was formerly a doctor’s clinic. All of the cocktails we’ve had here are absolute perfection and they also have a number of small bites and light entrees to choose from if you want something to go with your drink. 

TIP: Because it is a small place, reservations are highly encouraged and at times required. 

Location: 5312 Holmes Blvd. #B, Holmes Beach // MAP

READ MORE: Things to Do in Bradenton, Florida

Places to Eat on Anna Maria Island

The Donut Experiment

Donuts from The Donut Experiment Anna Maria Island near Sarasota, FL

The Donut Experiment has been one of my favorite stops on Anna Maria Island since it first opened. There’s nothing quite like getting a hot, cake donut with the icing and topping of your choice – which is exactly what you can do at the Donut Experiment! My personal favorites are chocolate with coconut and strawberry with Fruity Pebbles.

Location: 210c Pine Ave, Anna Maria // MAP

The Ugly Grouper

If you’re a fan or grouper or want to try grouper for the first time then I recommend visiting The Ugly Grouper which, as the name suggests, specializes in grouper menu items. This casual restaurant is located towards the south side of the island and has such a fun vibe! There is live music and outdoor games to be enjoyed every day.

Of course, I can’t talk about the food here without making some suggestions for grouper menu items. Of course, you can go classic with the grouper sandwich but if you want to try something a bit different I suggest trying the grouper reuben or the grouper tacos which are both superb.

Location: // MAP

The Cheesecake Cutie

Peanut Butter Dream cheesecake from The Cheesecake Cutie on Anna Maria Island - Sarasota desserts

The Cheesecake Cutie is located on nearby Anna Maria Island but it’s definitely worth a visit. Jennifer, the owner, brought her mother’s cheesecake recipes from New Jersey to honor her memory and first started by selling them to friends and family while they encouraged her to open her own shop which she did in 2019.

While Jennifer makes regular size cheesecakes my favorite is ordering the cuties which are mini cheesecakes the size of a cupcake! Our favorite flavors so far have been Peanut Butter Dream, Chocolate Raspberry, and Blueberry-Lemon.

In addition to their sweet mini cheesecakes, they also have a full menu for breakfast and lunch. 

Location: 3324 E Bay Dr, Holmes Beach // MAP
Hours: Monday-Saturday 7:30am-4pm, closed Sunday

The Sandbar Restaurant

Blackened fish tacos at The Sandbar Restaurant - Anna Maria Island, Florida | Sarasota Dining | Sarasota | Florida

The Sandbar Restaurant is an Anna Maria Island favorite. Not only do they have great food, but they are also located on the beach so you can easily leave the beach to dine here for a casual lunch and in the evenings, it’s a great date night spot.

I recommend visiting for lunch or timing your dinner around sunset because of their nightly sunset competition where if you happen to guess the correct time for sunset you can win a bottle of champagne! 

One of my favorite menu items to get at The Sandbar Restaurant is their fish tacos which feature a seasonal fresh fish (or you can upgrade to grouper year-round) ​​with a number of veggies with rice and black beans.

Location: 100 Spring Ave, Anna Maria // MAP

Rod and Reel Pier

Another Anna Maria Island staple is the Rod and Reel Pier which has been around since 1947. Rod and Reel is an affordable restaurant that is perfect for lunch or dinner and enjoy the sunset right by the gulf. Some menu favorites include the oyster po’boy and seafood dinner which has grouper, scallops, and shrimp.

Location: 875 N Shore Dr, Anna Maria // MAP

The Chateau Anna Maria 

If you’re looking for something that is a bit more upscale on Anna Maria Island then consider making a reservation at Chateau Anna Maria. I have yet to eat here but it’s been recommended to me enough that I have it on my list to visit soon. One thing that stands out to me is the expansive menu that caters to a wide variety of food preferences and dietary restrictions.

Location: 5325 Marina Dr Main Floor, Holmes Beach // MAP

I hope you enjoy these unique things to do on Anna Maria Island!

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