6. Boca Grande, Florida


The Gulf Barrier Islands off Florida's southwest coast define laidback lifestyle: Think Hemingway's Key West before the neon, noise and nonstop partying. Boca Grande on Gasparilla Island lacks traffic lights and chain stores, but it does have a century-old lighthouse, banyan tree-lined streets, and a converted railway station shopping complex showcasing local art. Land-based activities include hiking and biking along the former train tracks, or if you want to hit the water you can island-hop from Captiva to Cabbage Key (it's one

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