Written by Heather Burke
October 2021

Whether you’re a boater, beach bum or history buff, you will find Anna Maria Island an amiable oasis. This beautiful barrier island stretches almost eight miles, with Tampa Bay and St. Pete to the north and Longboat Key to the south. It’s shored by the Gulf of Mexico and by two bridges on the Intracoastal side from mainland Bradenton.

Pine Ave's Outdoor Jail - destinations - marinalife
Pine Ave’s Outdoor Jail | Wikimedia Commons

Anna Maria has been a captivating vacation spot for more than a century, casual and relaxed with an Old Florida feel. The island ebbs and flows with flocks of visitors and the continual tidal surf. You can imagine vacationers arriving in 1912 by steamship to Anna Maria’s City Pier (long before bridges) bound for the beach in Edwardian swimsuits.

Today’s beach goers come in boats, cars and trolleys to the expanse of white sand and turquoise surf. They swim and sunbathe, then seek refreshment at cool Bahamian beach bars and cafes, savoring crab and shrimp dishes often accompanied by Caribbean music and fiery sunsets fading into the Gulf.

Anna Maria offers more than surf and sand. Steps away from the beachy resort scene, discover Anna Maria City’s quaint downtown Pine Avenue, first established in the 1880s. Coastal boutiques and charming cottages extend all the way to the historic 1911 Pier where local fisherman drop lines daily. Don’t miss Pine Ave’s hilarious outdoor jail and fascinating (free) Anna Maria Island Historical Society full of memorabilia.

Farther down-island, Bridge Street in the Bradenton Beach section is enchanting with Key-West style inns, seafood restaurants and lively tiki bars like Bridge Tenders. Cortez Village across the ICW and bay is a real flashback, one of Florida’s most historic working fishing harbors.

Kayak or paddleboard around tranquil Spoonbill Bay’s lush maze of mangroves and spot pelicans and docile dolphins along the way, or boat out to Passage Key National Wildlife Refuge to observe dolphin, manatee and rays in Tampa Bay and off the shores of Anna Maria Sound.


Bradenton Beach Marina
The marina is located off the ICW at Marker 49, south of the Cortez Bridge. One mile to Longboat Pass, boaters have easy access south to the Gulf of Mexico. Overnight slips are available for vessels up to 60 feet, with laundry, fuel, on-site marine service, Wi-Fi and more. It’s a short walk to the beach and historic Bridge Street for shopping and dining. Dolphin tours and the Anna Maria Princess leave from this marina.

Anna Maria Island Pelican - destination - marinalife
Anna Maria Island Pelican | pxhere.com

Safe Harbor Pier 77
Just off Anna Maria Island on Perico Island by the Manatee Avenue Bridge is Safe Harbor Pier at The Compass. This new marina has transient space for boats up to 50 feet fuel, a ships store and laundry. The less-busy, protected harbor offers draw bridge-free access to the Gulf. Yacht guests can access the Caribbean inspired Compass Hotel for a fee ($20 pp). Take the free shuttle or Monkey Bus to beaches and dining. SUP, kayak or bike from the resort.

Waterline Villas & Marina
This resort has modern slips for boats up to 45 feet, and charters and tour boats dock here, too. Stay at this Marriott Autograph hotel (Holmes Beach does not allow overnight sleeping aboard) to enjoy the waterfront pool, amenities and nearby beach. The free trolley takes you to beach bars, shops and restaurants.


The Sandbar
This is the perfect beach bar to relax and dine on delicious food with your toes in the sand, drink in hand, and spectacular views of the Gulf. Try the succulent crab stuffed shrimp, wow! The menu is loaded with island-vibe cocktails, delicious fish, fresh salads, and many good eats.

anna maria pool - destination - marinalife
Courtesy of Greg Burke

Tide Tables at Marker 48
For the area’s best fish tacos, go to Tide Tables just over the bridge to the fishing village, Cortez. Sip a beer or wine on the docks while you wait for a coveted table with an amazing view of the ICW.

Beach Bistro
Beach Bistro is the exception to all the casual dining on Anna Maria. This romantic restaurant is fancy and fabulous, serving a multi-course prix-fixe menu, a tradition for over three decades. Make reservations well in advance, request outside dining on the beach or the elegant inside, and prepare for a culinary experience.

Ginny’s & Jane E’s Café & Coastal Store
This morning hot spot serves amazing (huge) fresh baked cinnamon rolls inside a shabby chic beach gift shop, formerly a humble grocery store. At first bite you understand why folks line up here for breakfast goodies — egg sandwiches, bagels and avocado toast — before heading to the beach across the street.