ANNA MARIA ISLAND
Drive time:1 hour from Tampa
Best for: Those who want to live like beach bums and pretend the rest of the world doesn’t exist
The Home: Renting an adorable cottage or beach house is de rigueur on Anna Maria Island, just south of Tampa. Our favorite is Limefish, from which a sandy path off the back porch leads to the shore. For a more modern sensibility, experience a week in a Frank Lloyd Wright-inspired home set on stilts high above magnificent sand dunes.
Eats: Don’t miss breakfast at Ginny's and Jane E's (annamariacafe.com) at the old IGA—a little shop with a café in the back that serves coffee and ridiculously yummy pumpkin bread. For a cool afternoon treat, indulge in homemade ice cream at Two Scoops (941.779.2422), opposite the city pier. Dinner is at the Sandbar (sandbar.groupersandwich.com), a local institution.
Explore: From Beach Bums (beachbumsami.com), rent brightly painted bicycles with baskets on the handlebars or a three-wheel Surrey bike that the whole family can ride on together with the shade of a canopy. Pop into local galleries and boutiques like Sand Dollar (myyellowshovel.com), a treasure-trove of sundresses, sandals and nautical-themed home accents. Keep biking till you reach the beaches, where you’ll find tidal pools—perfect for kids to play in—and sandbars—great for bodysurfing. A local favorite is Bean Point on the northwest tip of the island (look for the “Public Access” sign hidden behind the trees). With its wide expanse of white sand and crystal-blue water, you’ll swear you were in the Caribbean.
Don’t Miss: Find a wooden bench at the end of the Rod & Reel Pier overlooking Tampa Bay. The fishing here is great as long as you manage to catch them before the pelicans do. Stroll the weathered pier, made with engraved planks bearing names of local families who helped save the old pier in 2008. Upstairs is the Rod & Reel (941.778.1885) restaurant, which is as Old Florida as it gets. At this authentic fish shack, surrounded by schools of jumping fish and sea gulls circling overhead, the chef serves a memorable plate of fried shrimp.
Book: Pineapplefish (pineapplefish.com) offers everything from small cottages to four-bedroom beachfront homes. Seasonal rates: $1,550 to $4,500 weekly.
annamariaisland-longboatkey.com

By Vicky Hodges