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Beat the cold and drive to Key West

The beach on the southside of Key West, bar & grill in the distance
The beach on the southside of Key West, bar & grill in the distance
Michael Guadagno

Possibly the most unique city in the country, Key West is a Caribbean island you can drive to. The drive through the Florida Keys is one of the most scenic in the world. Visitors routinely take photos from their car or make periodic stops along the way because every view is worthy of a postcard. TripAdvisor.com calls the Overseas Highway, “A drive for your bucket list.” Key West boasts good weather year round, so driving conditions are usually great.

Peak season starts after Christmas when the snowbirds start to migrate south for the winter, but there is plenty to do throughout the year. The island is only three miles wide and six miles long and it’s jam packed with sightseeing activity. Most walking tours include Ernest Hemingway’s home and White House South, which was President Truman’s favorite vacation locale, but Presidents Eisenhower, Kennedy, Carter and Clinton also vacationed there.

Duval Street alone makes for a great walking tour because the avenue is replete with unique restaurants, bars, shops and entertainment. At the north end of Duval there is where you'll find the world famous Sloppy Joe's Bar & Grill. Plus there's a bustling shopping district, a fantastic aquarium that is partially indoors and partially outdoors, and the Mel Fisher Shipwreck Museum which houses gold bullion and artifacts recovered from two Spanish galleons that sank in a storm way back in 1622.

If relaxing at a seaside bar or patio deck is your idea of a great vacation, there are plenty of great spots for that as well, and several beautiful beaches for those who want their toes in the sand. Yoga on the beach is another popular way to unwind. Popular day trips include snorkeling, scuba diving, and deep-sea fishing.

There’s no shortage of great restaurants or tropical drinks. Check out Conch Republic, The Sunset Grill (where you literally can watch the sun set), or Two Friend’s Bar & Grill. Two Friends claims to make the best Pina Coladas in the world. Maybe it’s time to find out if that’s true.