Key West

The iconic red, black, and yellow concrete buoy marking the southernmost point of the continental United States, just 90 miles from Cuba. A Key West institution and one of the most-photographed landmarks in Florida — the short walk from Mallory Square through Old Town is itself a highlight.

The Spanish Colonial mansion where Ernest Hemingway wrote some of his most celebrated works — 'For Whom the Bell Tolls' and 'To Have and Have Not' among them. The house retains Hemingway's original furniture, personal artefacts, and his beloved pool; it is now home to over 50 polydactyl cats descended from his own.

A nightly gathering at the waterfront Mallory Square that has been a Key West tradition for decades — buskers, acrobats, fire-eaters, and the entire island community come together to watch the sun drop into the Gulf of Mexico. As much a cultural event as a sunset viewing.

A National Historic Landmark Civil War fort at the western tip of Key West, housing the largest collection of Civil War-era cannons in the United States. The park also encompasses Key West's best beach — calm, clean water with good snorkelling and far fewer crowds than the rest of the island.

An open-air garden restaurant in Bahama Village with a legendary reputation — roosters and cats wander freely between the tables, the bougainvillea overhead is in permanent bloom, and the food is reliably wonderful. Blue Heaven has been a Key West institution for generations, beloved for its indulgent brunches and relaxed Caribbean spirit.

A no-frills, cash-only Cuban restaurant in a converted house near the Southernmost Point, serving enormous portions of authentic Cuban home cooking to a loyal local following. The ropa vieja, Cuban sandwich, and black beans and rice are exactly as good as the regulars will tell you.

The oldest restaurant in Key West, operating continuously since 1909, with a wonderfully lived-in interior of old photographs, nautical paraphernalia, and decades of island history on the walls. The open-air back patio is a sun-dappled people-watching paradise.

A sprawling waterfront seafood restaurant in the historic seaport district, just a short walk from the cruise dock — a reliable go-to for fresh conch fritters, lobster mac and cheese, and locally caught fish with a direct view across the working harbour.

A tiny, beloved neighbourhood restaurant with no reservations and a devoted following — widely considered one of the finest tables in Key West. The menu changes daily based on what is fresh, but the gnocchi paired with local fish is the signature dish that people return to the island for.

Key West's most famous bar and a genuine piece of American literary history — Ernest Hemingway was a devoted regular, and the bar still celebrates his legacy with an annual look-alike contest. Live music runs from 11am to 2am every day, making it as much a live-music venue as a bar.

A laid-back, shaded wine and cocktail bar on a covered porch in the quieter part of Old Town — a welcome antidote to the Duval Street noise with a thoughtful drinks list, good charcuterie boards, and often a live acoustic guitarist on weekends.

A legendary Key West institution since 1890 with deliberately no air conditioning, no theme, and no pandering to tourists — just strong drinks, live music most nights, and a fiercely local atmosphere that has survived more than a century of island history. The walls are covered in eccentric art and generations of signed dollar bills.

A tiny, beloved walk-up coffee window near the Historic Seaport serving the best Cuban espresso in Key West — strong, sweet cortaditos and coladas poured the traditional way, alongside flaky guava pastelitos baked fresh each morning. Expect a queue; it is absolutely worth it.

A small, calm café on a quiet street just off the main drag — good espresso, loose-leaf teas, and fresh pastries in a relaxed setting that feels genuinely off the tourist track. Ideal for a mid-morning break when the Duval Street crowds start to build.

Consistently rated the best beach in Key West — sheltered, clean, and with the best snorkelling on the island directly off the rocky southern edge where the reef fish congregate. The state park setting keeps the crowds manageable and the water quality excellent.

Key West's longest public beach — a wide, accessible strip of sand along South Roosevelt Boulevard with calm, shallow water and affordable water sports rentals. More open and windswept than Fort Zachary, it attracts a local crowd and is a good option for families or those wanting equipment rentals at lower prices.

A full-day catamaran or seaplane journey 70 miles west of Key West to a remote island fortress — Fort Jefferson, the largest brick structure in the western hemisphere — surrounded by pristine coral reef and nesting sea turtle beaches. The snorkelling around the fort moat is world-class and the entire experience is unlike anything else in the Caribbean.

A 90-minute narrated sightseeing loop through Old Town, Bahama Village, and the historic districts aboard the famous open-air tram — a Key West tradition since 1958. An excellent orientation for first-time visitors, covering over 100 points of interest with entertaining commentary.

A morning or afternoon boat tour out to North America's only living coral reef, combining glass-bottom viewing sections with a full snorkel stop on the reef. Guides are knowledgeable marine biologists who identify the fish, corals, and occasional shark or ray sightings.

A guided kayak or paddle-board tour through the mangrove tunnels of the backcountry flats north of Key West — a magical, protected waterway where manatees, nurse sharks, tarpon, and spoonbills are regularly spotted. Small groups, knowledgeable naturalist guides, and a genuine connection with the Florida Keys ecosystem.