Unlike the rest of the towns on this list, winter is the busiest season in Key West. Swim, sunbathe, snorkel, kayak, parasail, or scuba dive in the crystal clear waters. Key West is well known for its beautiful sunsets, consider taking a sunset cruise for a front-row seat. Make sure to visit the heart of the Conch Republic Mallory Square and try some of the great seafood food. You’ll get a taste of the Caribbean without needing a passport.