Anna Maria Island may be one of the most unpretentious places left on the planet. No one’s consulting their schedule via smartphone or looking at the logo on your shirt. They’re too busy with more important things – like eating grouper sandwiches at funky little beach bars, kayaking with dolphins in Palma Sola Bay, fishing from an old wooden pier or watching the sky turn 10 shades of spectacular as the sun settles into the Gulf of Mexico. Life is simple here, and good – and even if you come for only a few days, you come away feeling better for that.

The Landscape
It’s more seascape than landscape, actually. Anna Maria Island is only two miles at its widest, much narrower in most places. No matter where you are on the island, you’re literally a minute or two from the bay or the beach. Geologically, topographically and temperamentally, it’s just what you’d expect from a tiny little island along Florida’s coastline: low-lying, sandy and chock full of casual, coastal charm.

The Accommodations
One thing that truly sets Anna Maria Island apart from other Florida beach destinations is the fact that corporate America seems to somehow have missed this little gem. In fact, there are no hotel chains on the island. Instead, you’ll find quaint, tropically colored cottages; small, charming inns; and friendly little mom ‘n’ pops.

The Locals
About 1,800 people live on Anna Maria Island, many of them seasonally. It’s a mix of retirees and snowbirds, along with the folks who contribute to the locally owned cafés, lodging properties, ice cream shops and nature tour businesses that make this place an amazing flashback to a more relaxed day and age. Island residents are a casual lot: If anyone here owns a tie, it’s for weddings and funerals. The locals know that they’re lucky to live on the island, and they’re happy you want to share the experience.

The Dress Code
Anna Maria Island’s dress code is decidedly come-as-you-are. For most residents and visitors, that means swimsuits, shorts, T-shirts and flip-flops. If you want to dress up for dinner out, bring a sundress, or shorts and a polo. Or don’t. That’s the beauty of the place.

The Weather
Anna Maria Island’s weather is nothing short of glorious. Bring a light sweatshirt in winter. In summer, cool off with those seaside breezes.

Average highs/lows by season:
Spring – 82°F/60°F
Summer – 90°F/71°F
Fall – 84°F/64°F
Winter – 73°F/51°F

The Transportation
Did you know Anna Maria Island offers FREE trolley service? Click here to see its route and schedule.