Maybe it’s the Hemingway connection, but I’ve always been fascinated with Florida’s Key West, an offbeat and slightly mysterious beach town in a state that, frankly, has not otherwise earned a spot in my list of top 10 favorite states. But man, I would love to just hop on a flight to Miami, rent a car, and take a leisurely three hour drive to Key West for a few days of sun and relaxation.
After checking in to the Historic Inn at Simonton Court (its renovated cottages were once workers’ quarters for an old cigar factory!), I’d fill my days with stand up paddle-boarding, airboat rides in the Everglades, biking around Old Town, visits to the Hemingway and Audubon houses, and of course, alternately lounging by the pool and the beach. Meal time would certainly mean fresh seafood, but I’m perhaps most excited to try brunch at Blue Heaven. Mmm, sautéed Key West shrimp over grits with Vermont white cheddar cheese, scallions and bakery fresh toast!? Yes please!
Keep in mind: As the southernmost city in the continental U.S., Key West is definitely subject to hurricanes, so try to avoid a trip during hurricane season (June 1 – November 30).
Bonus tip(s): If you’re looking for a great day at the beach, check out Bahia Honda State Park, about an hour and 15 minute drive from Key West. You’ll find some of the best snorkeling and beachcombing in Florida, and concessions and equipment rentals are available.