Key West is closer to Cuba than it is to Miami, and this shines through in its culture and cuisine. Make your way to the iconic Southernmost Point marker that marks 90 miles to Cuba. First-time visitors shouldn’t miss the home of one of Key West’s most celebrated residents—the Ernest Hemingway Home and Museum. Just a short jaunt away in the Old Town, the house looks exactly how it did when the writer resided in the Conch Republic, and descendants of his six-toed cat Snowball still roam the grounds. Nights don’t kick off until Sunset Celebration at Mallory Square, so be sure to arrive early and take part in the festivities before the show begins. You'll be in for a picturesque sunset that is definitely photo-worthy.