Get a Taste of Old Florida at This Charming Gulf Coast Beach Town

Eat seafood at one of the oldest fishing villages on the East Coast and explore other fun things to do in Anna Maria Island.

Anna Maria Island
Anna Maria Island | Photo courtesy of Bradenton Area Visitors Bureau
Anna Maria Island | Photo courtesy of Bradenton Area Visitors Bureau
Welcome to Two Days Away, our series featuring weekend-long itineraries within a five-hour drive of your city—because sometimes we all just need a little adventure fix.

Located just 45 minutes away from St. Petersburg, Anna Maria Island is a time-warp. The barrier island on the Gulf of Mexico has strict regulations that govern its development. So, unlike nearby coastal towns that are now covered with high-rise condos, the seven-mile strip of white-sand beach here is lined by natural dunes and low-rise, retro-feeling motels and homes. It’s this old-school vibe that has been making it an increasingly popular getaway for vacationers who want to feel like they’ve actually escaped modern life.

But just because it hasn’t been built up like the rest of the state, doesn’t mean there aren’t plenty of fun things to do on Anna Maria Island. From cruising the waterways and fishing to riding horses and eating local seafood right on the beach, we’ve got several reasons to make the trip out to this old Florida paradise.

Travel time:

45 minutes from St. Petersburg, Florida
4 hours from Miami, Florida

Cortez Village
Cortez Village | Photo courtesy of Visit Bradenton Gulf Islands

If you don’t do anything else: Visit one of the oldest continually operating fishing villages in Florida

Coastal Carolinians displaced after a hurricane set up a new community at Cortez Village, a National Register of Historic Places community, back in the 19th century. The area still boasts a working commercial fishery to this day, as well as a handful of old fish houses that serve just-caught seafood from the Gulf. You can’t go wrong at any of those places, but the most popular Cortez Village restaurants have got to be Cortez Kitchen, Swordfish Grill, and Star Fish Company, all of which allow boaters to pull right up to the dock.

Just around the corner, Tide Tables boasts a similar vibe with similarly great seafood including fish tacos and a fried grouper sandwich that have made it a go-to for locals. If you want to learn more about the historic village, head over to Florida Maritime Museum, set inside the original 1912 schoolhouse.

Photo by Matt Marriott, courtesy of Bradenton Area Visitors Bureau

Fill Your Days:

The emerald green and blue waters that surround the island are definitely one of the top attractions. Unless you know how to drive a boat, the best way to explore them (while burning off those fried grouper sandwiches you should be eating) is atop a kayak or paddle board. Pick up a rental from AMI Paddleboard Adventures, Beach Bums, or another local outfitter. If you get lucky, you might come across some curious dolphins who want to come and check you out.

Florida Beach Horses
Photo courtesy of Florida Beach Horses

Not into paddling? Ride a horse through the water. There are a couple different companies that offer beach horseback riding in Anna Maria Island. Both C Ponies and Florida Beach Horses regularly schedule waterfront rides where you can actually ride out bareback into Palma Sola Bay. Never ridden a horse? No problem, these beginner-friendly excursions are open to all levels of riders.

Whether you want to spot marine mammals, hook some fish of your own, or just drink beer while watching the sunset from the boat, options abound for Anna Maria Island boat cruises. Check out Shore Thing Tiki Cruises if you’re looking for a party vibe, Anna Maria Island Dolphin Tours for some flipper action, and, if a private fishing charter is more your vibe, reach out to Jarrod McKenzie Fishing for inshore and nearshore trips guided by an actual pro.

While you’re in Cortez, consider booking a “Painting with a Fish” session with a local artist at the Florida Maritime Museum. It's a modern (cleaner, and potentially less bacteria-laden) spin on Gyotaku, an ancient Japanese method of printing fish by directly painting and pressing it onto fabric. If you just so happen to have your own freshly caught fish to print, that can probably be arranged as well.

The arts community also shows off on Pine Avenue, Anna Maria Island’s main strip of restaurants and shops. Lined by pastel-colored structures, it earned the moniker “The Greenest Little Main Street in America” for its LEED-certified buildings, crushed seashell sidewalks, and edible community garden. While those eco-friendly aspects are nice, the real draw is the commerce. Fuel up on coffee at North Shore Cafe and donuts at The Donut Experiment, before hitting up Pink & Navy for beachy clothing (and make sure to check out the pre-loved rack for deals), Island Charms for unique jewelry, and cooperative vendor space Pineapple Marketplace for locally made goods.

Sandbar Seafood & Spirits
Photo courtesy of Sandbar Seafood & Spirits

Eat, Drink and Sleep:

Restaurants and bars in Anna Maria Island

Florida is home to tens of thousands of beachside restaurants. At most of them, diners have to settle for just looking at the shore—not on this beach. Some of the best Anna Maria Island restaurants actually boast tables right in the sand. Both Sandbar Seafood & Spirits and Beach House Restaurant serve local seafood, like grouper and mahi, and produce grown on owner Ed Chiles’ nearby organic Gamble Creek Farm. Beach Bistro offers four-course, French-inspired menus with dishes like Lobstercargot (Maine lobster prepared escargot style with herbs and garlicky butter) and duck breast with cognac-pepper demi glace. Or, if you’d prefer a more private experience, Sandy Toes Luxury Beach Picnics offers fully customizable sunset picnics.

Joie Inn
Photo courtesy of Joie Inn

Hotels in Anna Maria Island

This slice of highrise-free heaven may not have as many hotel options as, say, South Beach or the Keys, but the gems you’ll find on Anna Maria Island keep the laid-back vibes going. Mello on the Beach on Manatee Beach is a brand-new lodging option with one- to three-bedroom villas complete with chic decor. It may read a bit more modern than the surrounding old-school environs, but it has all the comforts of home. The Joie Inn is another new option with apartment-style rooms and a cheery feel, while the Autograph Collection’s Waterline Villas offer a front row seat to marina life with sleek accommodations.

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Sara Ventiera is a former editor at Thrillist.