The southernmost point in the Florida Keys archipelago is a far-flung yet fun-filled island city: Key West. It has 260 days of sunshine a year, and its bright conch-style houses demonstrate a strong Cuban influence – it’s actually nearer to Havana than Miami. With a rich cultural history and photo-ready landmarks, there’s plenty to look out for. Culture Trip’s local insiders share their recommendations.
One of the island’s most popular photo opportunities states exactly what it is on its red-and-yellow marker: it’s the southernmost point of the United States. As you might expect, there’s not much to see other than a brightly painted buoy, but this landmark is almost always busy with selfie hunters. Beat the crowds by getting here at dawn – and as a bonus, you’ll snag an ultra-dramatic sunrise shot. Recommended by local insider Alli Griffiths
Key West’s main street runs the length of the island, from the Gulf of Mexico in the north to the Atlantic Ocean in the south. Although just a mile long, it’s here that you’ll find some of the best bars, restaurants and shops. You can’t leave the Florida Keys without trying key lime pie; Key West’s best is at Kermit’s Key West Key Lime Shoppe. For something to drink, one-time resident Ernest Hemingway favored absinthe, but a more palatable choice is the Hemingway daiquiri at Caroline’s Other Side, just a few steps off Duval Street. Recommended by local insider Alli Griffiths
Key West is often described as the place where the road ends, but as the number on this sign indicates, it’s also where the road begins. The photo-ready green and white sign marks the beginning of US Route 1, which runs all the way up the East Coast to Maine. To claim the coveted “I was here” shot, you can either walk up through the city center or take the hop-on, hop-off tourist trolley that can be hailed throughout the town. Recommended by local insider Alli Griffiths
This shell-pink turreted hotel oozes Victorian grandeur. It’s one of Key West’s best-known buildings, as it lies just one block away from the Southernmost Point, deeming it officially the southernmost hotel in the USA. If you’re unable to stay in one of its ornate rooms, slink off to the open-to-all poolside bar to enjoy the ambience over a sundowner or two. Recommended by local insider Alli Griffiths
Presiding over Mallory Square is this impressive red-brick building that dates back to 1891. Its intricate design stands as a testament to the wealth that poured into Key West at the turn of the 20th century, thanks to its lucrative trading routes and booming maritime industries. After brief stints as a post office and a court, today’s Custom House is a museum containing artefacts that reflect two centuries’ worth of Key West history. Recommended by local insider Alli Griffiths
