Off the southernmost coast of Florida sits Key West, a small island whose slogan may as well be: Come as you are. Walking down Duval Street (which is basically the Bourbon Street of Key West), you’re just as likely to see a group of older tourists in shorts and sneakers as a throng of gay men in tank tops and gold jewelry. You’ll also see everyone sipping from plastic cups, as open container laws do not apply here.
There’s no doubt that Key West is a drinking town, but it has so much more to offer: beautiful beaches, cultural and historical sites (like Ernest Hemingway’s former home), national parks, and water sports like paddleboarding, snorkeling, and windsurfing. (The temperate water means you can swim year-round.) Old Town Key West is beautiful to wander—it looks like a cross between Charleston and Savannah with its palmetto-lined streets and brightly-colored houses.
When it comes to getting to Key West, it’s choose your own adventure. Many cities offer direct flights to Key West International Airport. You can also drive by following U.S. 1 South as far as it goes, crossing the Seven Mile Bridge, which offers gorgeous views of the blue-teal waters. If you happen to be in southwest Florida, you can take a ferry from Fort Myers Beach or Marco Island—but sail at your own risk. If the water is choppy that day, you could end up sea sick for the 3.5-hour journey (this happened to my husband—sorry, sweetie!).