Top Things to See & Do on Anna Maria Island
Anna Maria Island is known for its Old Florida vibe, where folks come to unwind for a few days and sometimes end up staying permanently because of its friendly, unhurried atmosphere.
Background
The Island was first settled in the mid-19th century by Tampa Mayor Madison Post. He named the 7-mile long strip of land for his wife Maria and his sister-in-law Anna.
One of the original island residents instrumental in developing the town’s layout in the late 1800s was also the genius who came up with the recipe for the Fig Newton.
If you choose to fly, the nearest airport is the Sarasota Bradenton International Airport, about a half-hour drive away.
Parking on the Island is limited. Arrive early in the day to snag a good spot where parking is allowed. One of the biggest pieces of advice I can give you - pay attention to signage on residential streets to know where you can and can’t park, especially if you’re spending a few hours at one of the beaches.
Visitors rent bikes, golf carts or use the free trolley to get around the Island. When it comes to bikes, there are several companies that offer a variety of bike styles at differing prices.
The beaches on Anna Maria are some of the most picturesque you’ll find in the state of Florida. And with strict rules preventing high-rises from springing up on the Island, there’s very little obstructing those perfect views. Below is a list of the seven beaches you’ll find on Anna Maria.
* Holmes Beach
* Manatee Beach
* Beach at Bean Point
* Cortez Beach
* Coquina Beach
* Bradenton Beach
* Bayfront Park Beach
Now that you have some background, it’s time to dive a little deeper into the top things to see and do on Anna Maria Island.
Anna Maria Historical Society
402 Pine Ave, Anna Maria, FL 34216
Monday-Friday 10am - 1pm.
Closed Saturday and Sunday.
Closed the month of September.
Free admission. Donations welcome.
The Anna Maria Historical Society is the best place to start your exploration of the Island.
Inside the museum, you’ll learn eccentric tidbits about the area from historic photographs, artifacts and local historians themselves.
On the grounds outside is the Belle Haven Cottage which served as a fish packing plant, bait shop and rental house before it fell into Tampa Bay in the 1920s. Pulled from the waters, it functioned as a family home on the island for decades before being rescued from demolition and moved to the museum.
Also on property is the Island’s most famous photo-op. It’s the Old City Jail that was constructed in 1927 to detain local troublemakers and the rowdies who had a little too much to drink at the local roadhouse. The building caught fire in the 1940s, leaving it with no roof, no window bars and no door. The landmark once was featured in Ripley’s Believe it or Not.
Anna Maria City Pier
100 N Bay Blvd, Anna Maria, FL 34216
The original Anna Maria City Pier stood at this location more than a century and extended hundreds of feet into the turquoise waters of Tampa Bay. When it was first constructed, the pier was for boat traffic for folks from St. Petersburg arriving by steamship.
After years of abuse from tropical storms, Hurricane Irma in 2017 put the original out of commission for good.
A shiny new 678-foot pier has taken the place of the old one. Admission onto the pier is free with parking available along South Bay Boulevard. There’s also a trolley stop in the parking lot.
At the end of the wooden walkway you’ll find a small place where you can grab something to drink and relax on the benches while enjoying the tranquil waters.
On clear days, you can even see the Sunshine Skyway Bridge that connects St. Petersburg to the north with Bradenton and Sarasota to the south.
Bring your fishing pole to catch your own dinner. Fishermen love this place.
Rod and Reel Pier
875 N Shore Dr, Anna Maria, FL 34216
The Rod and Reel Pier has been serving up a little bit of Old Florida since 1947. Enjoy casual dining for the whole family from the two-story, newly renovated restaurant at the end of the pier or enjoy a drink at the bar where many locals hang out.
The restaurant is open for breakfast, lunch and dinner.
Historic Bridge Street Pier
200 Bridge St, Bradenton Beach, FL 34217
The Historic Bridge Street Pier in Bradenton Beach is a former bridge that back in the early days functioned as the only means to access the Island.
Anna Maria Oyster Bar can be found here, and along the street leading to the pier are plenty of shops and restaurants that will keep you busy for a couple of hours.
Bean Point Beach
793 N Shore Dr, Anna Maria, FL 34216
With so many miles of shoreline, just keep driving west toward the Gulf and you’re going to find a beach you’ll love.
But our favorite beach is a little more secluded at the northern tip of the Island.
It’s known as Bean Point, named for George Emerson Bean, the first permanent resident of Anna Maria Island. It was here where Bean’s original homestead was located.
The main entrance to the beach is at the intersection of North Bay Boulevard and North Shore Drive. But we usually take a canopied walkway between two houses just a street to the south.
If you drive a vehicle, be prepared to make a few passes through the neighborhood before landing a spot. Parking regulations are strictly enforced. Pay attention to the signs and only park in designated areas with your tires off the asphalt. If you don’t follow the rules, you’ll have a nasty surprise to take back home along with that nice tan.
Walking out onto the beach for the first time is like finding heaven on earth.
The sand here is so white and pristine that if you didn’t know better, you’d swear you found a place in Florida where it actually snowed.
If you’re looking to take in the perfect beach sunset with unobstructed views, Bean Point is the place and that is why it is the best beach on Anna Maria.
Pine Avenue
Every town needs a main street and here in Anna Maria, that main street is Pine Avenue. In addition to the Historic Society that’s located on Pine, you’ll find an abundance of gift shops, clothing boutiques, art galleries, restaurants, and plenty of spots to tempt your sweet tooth.
We enjoy popping into the Shiny Fish Emporium with its whimsical selection of gifts. This is a great stop for the kids because they sit down and paint their own sand dollar and take it home as a souvenir.
Another place where you’re sure to find a unique piece of the Island to remember your stay is at Emerson’s Studio Store. Owned by former Cincinnati Post cartoonist Emerson Quillin, his gallery is fun and offbeat, guaranteed to bring a smile to faces young and old.
Pineapple Marketplace is a one-stop shop for collectors, treasure-seekers, and anyone who loves a good find. It’s a locally-owned co-op with over 30 different vendors.
Two Scoops
101 N Bay Blvd, Anna Maria, FL 34216
Two Scoops offers 32 flavors of homemade ice cream with some “no sugar” options available. The ice cream is so good here you will not want to stop at just two scoops. They also serve up sandwiches and breakfast items.
Pizza Social
308 Pine Ave, Anna Maria, FL 34216
No hyperbole intended when I say we might have found our new favorite pizza joint. Located next to the Shiny Fish Emporium is Pizza Social.
I’m a sucker for those tiny slices of pepperoni that have a bold flavor and crisp up when they’re baked. They’re called Old World Pepperoni, or Cup and Char, and they serve them on their pies here at Pizza Social.
The dough and pizza base are made from scratch and cooked in their imported Italian oven.
Ginny's & Jane E's Cafe and Gift Store
9807 Gulf Dr, Anna Maria, FL 34216
The most important meal of the day can also be the most fun when you go to Ginny’s & Jane E’s Cafe first thing in the morning.
Housed inside a former IGA supermarket, the space is one of the most eclectic you’ll find. Meander through the coastal store, a unique collection of local art and unusual home furnishings.
Toward the back is the cafe with its mismatched tables and chairs, some big enough for a family - others tucked away in a quiet corner.
Open for breakfast and lunch, they’re known for their decadent cinnamon rolls.
The Doctor's Office
5312 Holmes Blvd. #B, Holmes Beach, FL 34217
No vacation on the Island is complete without a trip to The Doctor’s Office. This appointment-only craft cocktail bar occupies a 50’s retro building where generations of Islanders received medical care.
The bar commits to its medical theme with drink names like “Painkiller” and “Preferred Remedy,” customers always referred to as patients, and every order written as a prescription.
There’s also doctor-approved bar fare on the menu from soups and salads to sandwiches and cheese plates.
This place is just what the doctor ordered for an authentic Island nightcap.