Beach Town Smackdown: Anna Maria Island Vs. Siesta Key

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As the temperature heads south, so do tourists. And when it comes to sunny retreats, nowhere offers as many options as Florida. Two communities, just 23 miles apart on the Gulf of Mexico, top many travelers’ bucket lists: Anna Maria Island, which ranks third among Trip Advisor’s “Top 10 Islands in the U.S.” list for 2014, and Siesta Key, which sits at number three on the list of best beaches.

Anna Maria Island: Old Florida Charm

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Illustration by Sarah Lawrence

Your first stop: Anna Maria Donuts. Try to not salivate while watching the staff bake vanilla cake doughnuts, then dress them with your choice of icing—vanilla, chocolate, caramel, maple, powdered sugar or cinnamon—and one of 14 toppings, including coconut, crushed Oreos and bacon. These treats are worth their calories in gold, so make sure you squeeze in a visit by 1 p.m., as the shop keeps limited hours.

While you digest, take a stroll down Pine Street, where you’ll find the Anna Maria Historical Society Museum and Old City Jail, an open-air facility built in 1927 to house drunks, which left it to the mosquitoes to discourage repeat offenders. This street teems with shops—none of which hawk the kitsch ubiquitous in rowdier beach towns (read: no air-brush bikini tees here). Instead, you could snag an Acacia swimsuit and Hayden Reis tote at Pink & Navy, a Sazerac-scented candle at Bella By the Sea, a Flora Bella caftan at Shiny Fish Emporium and a Lilly Pulitzer cocktail dress at The Island Cabana.

Your appetite revived, you now have the difficult task of picking where and what to eat for lunch. There’s no shortage of places with beachy ambience. Two restaurants, The Rod and Reel and The City Pier Restaurant, sit atop Tampa Bay, while others, including The Waterfront, offer views of it. The island’s restaurateurs pride themselves on serving the daily catches of local fishermen, so give credence to specials when deciding between the grouper and mahi-mahi.

If fish is not your flavor, the island has two famous burger joints: Skinny’s Place and Duffy’s Tavern. A lease dispute in 2002 left Skinny’s with the beach shack that had been Duffy’s since 1958—Duffy’s relocated to a refurbished body shop—and locals subsequently took sides. However, many burger aficionados remain neutral and will just say that both places serve exceptionally thick and juicy patties starting at five dollars, and both accept cash only.

To get up close and personal with this seven-mile-long barrier island (and to mitigate the effects of breakfast and lunch), pick up a bike from Beach Bums. You may notice the dearth of mega mansions, high rises and sleek resorts popular just a few miles south on Longboat Key and in Sarasota. Anna Maria Island’s aesthetic leans toward Old Florida charm with cottages, bungalows, Cracker farmhouses and homes built on stilts. Many of these places are rental properties that fill up quickly with snowbirds from January to Easter and families in the summer.

For a picturesque finish to the day, nothing tops The Sandbar. Though the restaurant claims to have “the freshest seafood on the island,” it’s not the conch fritters or salmon pate (good as they may be) that drive diners here in flocks, but the unparalleled setting for sunset. Refurbished in 2012, The Sandbar, which abuts the Gulf, features an open-air dining room that extends right onto the beach. Every evening, waiters ask guests to predict (down to the seconds) when twilight officially starts, and the winner receives a bottle of bubbly. But most agree that simply seeing the fiery sky is a more than adequate consolation prize.

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