fb-pixel Skip to main content

ANNA MARIA ISLAND, Fla. - “Can you get arrested in Florida if you drive half-naked,’’ I asked. “Better not risk it, the way our luck is going,’’ Pam replied.

The airline had misplaced our luggage, so I was still wearing the Boston winter uniform of Uggs and fleece. The air conditioning in our (cheapo) rental car was spewing hot, funky fumes. Not to mention, we were lost. Sweaty and crabby, we stopped at a convenience store for a blast of cold air and a couple of diet sodas. The guy at the counter calmly directed us to our lodgings. “I’m gonna sweeten up this day for you,’’ he added, tossing a handful of chocolate candies into the paper bag with our beverages. “No charge. Enjoy,’’ he said.



Prepare yourself for a shock: People really are this friendly on Anna Maria Island, a 7.5-mile stretch of sand, surf, and old-fashioned charm. That weird elation you are experiencing is not a sugar buzz, it’s from the people who make random conversation with you, allow you to merge into traffic (with a friendly wave, no less), and dole out free candy kisses when you need them. These people really do exist, and they are right here, enjoying the good life on Anna Maria, one of the Gulf Islands off the coast of Bradenton in southwest Florida.

Even by Sunshine State standards, Anna Maria is one mellow joint. There is exactly one high-rise building here, which somehow sneaked past the town planners, but otherwise, three stories is the limit. Fast-food franchises are few. Mom-and-pop-type motels and cottage colonies rule. Stores sell such vacation necessities as inflatable alligators and purple Slurpees. “This island is 40 years behind the times,’’ resident Linda Haack told us. “It’s like the rest of Florida used to be, just beaches, palm trees, and pelicans.’’


True. Once you’ve crossed the drawbridge from Bradenton to Anna Maria, you feel the decades fall away. And stress? What stress? Within minutes of squishing our toes in the sand, we were seduced by the slo-mo rhythm of this easygoing island.

Hit the beach

As any sun-starved, winter-weary New Englander knows: It’s all about the beach. Luxuriously wide, and fringed by sea oats and Australian pines, Anna Maria’s crushed-coral beach is as soft as powdered sugar. Plus, the sand is so white, “I thought it was snow when we rolled into town in January,’’ said Michigan transplant Mary Ostrander. (She went back to her home state just once - to sell her house.) The topaz-blue waters of the Gulf of Mexico provide a dazzling contrast. All island beaches are open to the public. Manatee Beach is the busiest, with lifeguards, restrooms, volleyball, a beach shop, and the Café on the Beach, where everyone goes for pancakes in-the-rough. “Eating pancakes in your swimsuit, what could be better?’’ said Jackie Blank of Roanoke, Va., digging into a buttery stack. Coquina Beach, named for the tiny coquina shells strewn on the sand, has barbecue grills, making it a popular spot for a DIY dinner.

Celebrate local color

Watching the sky turns shades of sherbet over silvery surf is a cause for celebration here. Just don’t expect a wild, Key West scene with body painting and fire juggling. This is Anna Maria, after all. On our first night, we hit the Sand Bar, an open-air haunt where a local singer provided a fitting soundtrack - Jimmy Buffett cover songs - and couples strolled along the beach hand-in-hand. Another night, we made the sunset scene at the Bridge Street Bistro, where they toast the setting sun with a drink called the Green Flash, and everybody sings “You Are My Sunshine’’ without a hint of irony.


Strictly by accident, while looking for a place called Beer Can Island, we discovered a great walk: the Coquina Baywalk at Leffis Key. A rustic footbridge and boardwalk traverse tidal lagoons and shallows rich with birdlife (it’s one of the spots along the Great Florida Birding Trail). A closer look reveals a medley of sea creatures such as blue and fiddler crabs, whelks, and ruffled, snail-like mollusks called ragged sea hares.

On the advice of a family of Canadian tourists, we took the Island Trolley to 101-year-old Anna Maria City Pier, where anglers of all ages go to test their luck. Turns out they don’t rent fishing gear there - you need to go to nearby Beach Bums for rentals, and we were too lazy to do that - but we hung out long enough to hear about the ones that got away. “I swear it was a tigertail shark,’’ a tween boy told us, as we stepped over a wriggling mass of footlong fish. “Huge. Almost pulled me into the water before it got away,’’ he said.

Adventures on the water


We’re not really fisher-folk, but we do love some kayaking. And this island offers lots to explore, including lush little pockets of Old Florida in the nooks and crannies of the Intracoastal Waterway and Palma Sola and Sarasota bays. The man who knows it best is Shawn Duytschaver of Native Rentals/Native Sports, a sixth-generation islander who runs guided kayak tours to nature-rich outposts in Perico Bayou and Robinson Preserve. Lying just beyond Palma Sola Bay, Robinson Preserve is a primeval zone of crystalline pools, mangrove forests, oyster bars, and grass flats. We followed Shawn in our kayak, ever so quietly, hoping to encounter some of the wildlife that live in this 500-acre estuary - bottlenose dolphins, manatees, white ibises, brown pelicans, and roseate spoonbills among them. We didn’t see a manatee, but we did spot a pair of nesting bald eagles.

Dutyschaver is also the go-to guy if you want to try stand-up paddling (SUP), the marriage of surfing and kayaking. “It’s like walking on water, and it allows you to explore some of the most beautiful, unseen places around the island,’’ he told us. And so, this is how the days go on an Anna Maria Island vacation: lounging on the beach, body surfing in the waves, paddling a kayak, napping in a hammock, maybe beach-hopping by bicycle. As for shopping, well . . . there are a couple of gift shops on the north end of Anna Maria, but for real temptation, you have to go off-island. A short drive south toward Sarasota (via tony Longboat Key) leads to St. Armands Circle, a luxe loop of boutiques and galleries reminiscent of Nantucket.


Dining out was a happy surprise. Who knew this tiny islet would have some of the best fine dining in the state? We splurged on great meals at the widely-acclaimed Beach Bistro, and at Euphemia Haye, on Longboat Key, but the island’s casual, cheaper restaurants won us over, too. We loved the humongous fruit parfaits at Gulf Drive Café (where overeager seagulls hover, waiting to snatch unguarded french fries).

For dessert, we ate a few of those chocolate candies as we walked the beach. Life is all about the simple pleasures on Anna Maria Island.

If you go...

Where to stay

Rates are for February-April.

Harrington House 5626 Gulf Drive North Holmes Beach



The only bed-and-breakfast inn on the island is also one of the most highly-rated in the state. No children under age 12. Rooms $208-$359 (beach houses are more).

Bungalow Beach Resort 2000 Gulf Drive North Bradenton Beach



Renovated 1930s cottages on the beach. Rates $199-$379.

Tortuga Inn 1325 Gulf Drive North Bradenton Beach



This well-maintained resort offers 55 hotel rooms (with mini-kitchens), apartments, and suites (with full kitchens). Rates $180-$445.

Where to eat

Beach Bistro 6600 Gulf Drive, Holmes Beach


Award-winning, high-end dining on the beach; six-course tasting menu $100.
Euphemia Haye 5540 Gulf of Mexico Drive Longboat Key



Chef-owner Ray Arpke works his magic in a historic cottage. Favorites include Shrimp Taj Mahal (jumbo shrimp in curry sauce) $34, and crisp roasted duckling with bread stuffing and fruit sauce $38.50.

Gulf Drive Café 900 Gulf Drive Bradenton Beach



They serve breakfast all day here, in huge portions. Try the fruit parfait, a giant goblet of yogurt, fresh fruit, granola, and honey $7.29, or café hotcakes and three eggs $5.99.
Mr. Bones BBQ 3007 Gulf Drive, Holmes Beach



A rarity that serves barbecued ribs and vegetarian Indian food. Most everything on the menu is $15 or under.

Diane Bair and Pamela Wright can be reached at bairwright@ earthlink.net.