2 Best Sights in The Florida Keys, Florida

This was one of the first of the Upper Keys to be permanently settled. Early homesteaders were so successful at growing pineapples in the rocky soil that, at one time, the island yielded the country's largest annual crop. However, foreign competition and the hurricane of 1935 killed the industry. Today, life centers on fishing and tourism, and the island is filled with everything from bait shops and charter boats to eclectic galleries and fusion restaurants.

Originally two islets, this area was first inhabited by Native Americans, who left behind a few traces of their dwellings, and then by farmers and fishermen who built their homes here in the mid-1800s. Henry Flagler bought the land from homesteaders in 1908 for his Florida East Coast Railway, filling in the inlet between what were then called the Umbrella Keys. Today, this is where you'll find Theater of the Sea, the famous Holiday Isle (now Postcard Inn), and Windley Key Fossil Reef Geological State Park.