Best For
Beach-town devotees who want the works: long beach walks, cute beach boutiques, chilled-out beach cafés, funky beach bars. If you’re craving an authentic taste of island living, Anna Maria Island is the real deal. This seven-mile stretch of white sandy shores and crystal-clear water sparkles in the sun’s spotlight, yet not many know of this, shall we say, secret spot perched on the Gulf coast. The island revels in its small-town vibe, where building anything over two stories is a no-no. So expect lushly landscaped clapboard homes and quaint inns, plus a scattering of colorful beach-chic shops and eateries. And the best thing? It’s only an hour or two from St. Petersburg, Sarasota, Tampa and Orlando.
Like A Local
The ideal way to experience Anna Maria is to rent your very own beach cottage. Trust us, great options abound here. First choice is naturally a place on the water, but no matter where you land, you are certainly never far from the Gulf or Tampa Bay. Wake to a sunrise over the Intracoastal Waterway from the private deck of Casa Bella, one of many rental homes, or just bird-watch while floating on your back in the house’s infinity pool. Even indoors it’s nature-centric. You’ll feel like you can reach through the living room’s window and touch the ripples in the bay from the comfy sofa — it’s literally right there.
Go South
Anna Maria starts out as a wide maze of residential lanes in the north, tapering down to a single narrow road as you reach its southern tip, where one of the best beaches caps off the island. Coquina Beach is a gorgeous strip of easy-to-access public beach with wide, flat expanses of sand blending into quiet Gulf water. Our favorite spot is south of 13th Street, where it’s completely undeveloped. Soft, shady pines line its eastern edge, and people snorkel around its mini limestone jetties where an occasional dolphin pokes its head out of the water. Boat enthusiasts hang at the southern- most point to watch sailboats of all sorts navigate through Longboat Pass. Bradenton Beach, the south end’s hub, is where to go to feast on strawberry jam crêpes, croissants and even French toast. Parisian chef Olivier Rose makes them at the cozy Island Creperie. Take a peek at the jewelry and local artwork displayed on driftwood and dried sea grape leaves in Hive Creations. The Historic Bridge Street Pier is where pelicans harass fishermen returning from a day on the water. It’s also home to the deceivingly ramshackle but friendly Joe’s Eats and Sweets, serving deliciously fresh banana splits.
Go North
The City of Anna Maria anchors the northern end of the island. Tight sandy lanes lined with inns and eateries open up to boulevards where thick foliage obscures rows of houses. If you search hard enough, you’ll find Bean Point, the locals’ favorite beach. While Coquina Beach is super accessible on the southern end, Bean Point is a completely in-the-know secret spot tucked away at the island’s northern tip. Amid the sprawling mansions on North Shore Drive, there are a few hidden walkways. If you can find street parking, you’ll be treated to graceful dunes with clusters of yellow wildflowers and the softest white sand kissed by Caribbean-clear emerald waters. Wade out to a sandbar for a view of the pristine beach that curves around the island and disappears into the distance. Pine Avenue, with galleries, boutiques and cafes, is perfect for strolling. Among the shops at the historic Green Village, an assemblage of newly restored Old Florida cottages, is Island Cabana, where a collection of classic whitewashed pottery and vintage etchings of corals and pelicans tempt shoppers. Hop on one of the free old-fashioned trolleys heading back south. En route in Holmes Beach is the brand-new Eat Here restaurant, the casual sibling of the well-known upscale Beach Bistro. Art covers the walls, and tables overflow with plates of Cedar Key clams and Pelham frites — crispy fries with gravy — paired with Saison Athene beer from the Saint Somewhere Brewing Company in nearby Tarpon Springs.
Wrap The Day
For the ultimate sunset experience, book a table at the Bridge Street Bistro, located in the Island Time Inn. You’ll want to request one of the balcony tables facing the Gulf. The view from this third-story perch begins at palm trees blowing in the sea breeze and extends to the horizon. Hands down, the succulent Grassy Key grouper with a light, buttery lime sauce is the dish to order. Finish off your meal with the berry basket dessert. The almond-crust bowl filled with the freshest strawberries, raspberries and handmade cream is even better than the sunset. amilbk.com
More Favorite Beaches
- Siesta Key – From morning marathons to sunset cocktails, Siesta Key is a favorite gathering spot in the Sarasota area. A resident sculptor surprises with dinosaurs and castles in the sand.
sarasotafl.org - Clearwater – Watching the sun set from a gulf-front luxury suite at the Sandpearl Resort spells total indulgence in paradise.
visitstpeteclearwater.com - Cayo Costa – Take a ferry or private boat to this white ribbon of sand off Charlotte Harbor. It’s just you and the seabirds.
floridastateparks.org - Gasparilla Island – It was tarpon fishing that first put Gasparilla Island on the map. Today, its little town Boca Grande is sought out for its sparkling Gulf waters, chic boutiques and inn.
the-gasparilla-inn.com - Captiva Island – After a sunset dip in lush Gulf waters, stroll over to the island’s one-block downtown for live music and cool cocktails.
fortmyers-sanibel.com - Sanibel Island – Be sure to bring a mesh bag to Sanibel Island, the shelling capital of Florida (low tide reveals the best shells). Keep an eye out for dolphin pods just off the shore.
fortmyers-sanibel.com - Barefoot Beach – Find the quieter side of Naples with a visit to Barefoot Beach, where palm trees guard the shoreline. Half the fun is ogling opulent homes on the way to the sand.
paradisecoast.com - Marco Island – Stay at a top resort on a half-moon beach, then venture into the Everglades.
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