Anna Maria Island, Florida
There are no high-rise condos or greasy golden arches. Gulf Drive cuts down the center, and canals branch off from the interior, creating a plethora of water-accessed homes. Instead of a car, it’s more likely you’ll use your bike, kayak, or flip-flops. You know the nights are quiet when turtles choose your beach to lay their eggs.
There’s only one course on the island, the private Key Royale Club, but this is Florida after all, so there’s plenty of public and semiprivate golf to be had up to a half hour away on the mainland. Anna Maria’s vibe is decidedly more artsy paddleboard-and-cruiser bike than exclusive yacht club.
Your Main Street has: Rod and Reel Pier, for a fresh seafood-omelet breakfast and a glimpse of a dolphin or manatee out the window. The north side of the island is basically all one quaint Main Street. Go to Ginny’s and Jane E’s at the Old IGA for coffee, baked goods, home furnishings, and good company, or the Beach Bistro for the occasional dinner splurge where flip-flops are still welcome.
Your favorite place to eat could be: Sandbar Restaurant. It sits on the water’s edge, and each night patrons compete for the free bottle of Champagne given to the diner who guesses the time of sunset.
On the weekend you might: Take the complimentary trolley to a different beach each day. Residents aren’t afraid to leave the island, either, for major sporting events in Tampa and Sarasota art festivals within an hour-long drive.
Visiting Anna Maria: Stay a week: Island Garden Villas has six one- or two-bedroom villas, complete with bikes to help you blend in with locals. Rates from $775 to $1250/week; islandgardenvillas.com. Stay a month: Two-bedroom, two-bath waterfront beach cottage rental with pool and dock; vacationrentals.com (Listing ID 10950).