Every sunset is literally a party at Mallory Square, where tourists, street performers, and people who’ve stumbled over from Duval Street converge to watch the day end over the water. “My suggestion is to work your way down the seaport, get a bite to eat or drink at Turtle Kraals there, then end up in Mallory Square for the sunset celebration,” says Dennison. “Everybody who stays with us says that’s their favorite thing.” In high season it can get packed, so scope out your spot early. There’s no shortage of bars that’ll serve you a drink to go, or musicians who will entertain you until showtime.
The 169-year-old Key West Lighthouse was originally built to help ships headed to the US Naval Station, and stood as a beacon to ships along the coast of Florida for some 120 years. Interestingly, when it opened in 1848, it was helmed by one of the first women to hold that job in US history. Now it’s a historic site across from the Hemingway Museum, where you can climb the 88 steps to the top for a sweeping view of the island.