If your idea of paradise involves sea breezes, gleaming decks, and the gentle sway of a yacht, Key West and nearby Stock Island are destinations you won’t want to miss. Nestled at the southernmost tip of the U.S., this corner of the Florida Keys offers everything from world-class marinas to luxurious sunset sails. Whether you’re sailing in aboard your own vessel or staying dockside, Key West welcomes all who crave saltwater serenity.

Explore the Harbors and Marinas

Key West Harbor and the marinas on Stock Island are a sailor’s dream. From the iconic Galleon Marina and Conch Harbor to the full-service Safe Harbor Marinas, the docks are filled with sleek yachts, charming sailboats, and liveaboards. Even if you’re not captaining a boat yourself, strolling the harbor with a morning coffee is a treat for the senses, offering up views of classic schooners, state-of-the-art catamarans, and the friendly hustle of dockhands.

Guided Sailing and Boating Tours

For those without a boat, guided sailing tours are an incredible way to experience the magic of the water. Choose from half-day catamaran cruises, classic schooner outings, or private yacht charters complete with onboard dining. These tours are perfect for couples, groups, or solo travelers looking to mingle with fellow ocean lovers.

Sunset sails are particularly popular, offering a front-row seat to one of the most spectacular shows on the island. Sip a glass of wine, feel the wind in your hair, and watch as the sky turns cotton candy pink over the sea.

Discover the Waters with Fishing Charters

If you’re more into casting lines than lounging on deck, Key West offers some of the finest fishing charters in the country. Fish All In Charters, run by experienced captain Garret Frey, provides an all-inclusive adventure for anglers of every level. Whether you’re trolling for mahi or bottom fishing for snapper, the turquoise waters are teeming with opportunity. Click to learn more about the latest catches and trip options.

Dockside Dining and Fresh Catches

When it’s time to dine, there’s no better place than the seafood shacks and upscale eateries scattered around the marinas. A must-stop is Eaton Street Seafood Market, a beloved spot for fresh, local fare. Grab a lobster roll or sample their famed stone crab claws, all in a laid-back, nautical setting perfect after a day on the water. Click here to view their seafood specialties.

Snorkeling, Kayaking, and Eco Tours

Beyond sailing, boating in Key West can also take the form of nature exploration. Guided eco tours through the mangroves or snorkeling excursions to nearby reefs offer a chance to see sea turtles, tropical fish, and coral gardens. These excursions are often led by marine biologists or expert guides who share insights about the island’s delicate ecosystems.

Overnight Aboard or Waterfront Hotels

For boating enthusiasts who prefer to sleep near the water rather than on it, there’s a wide selection of waterfront accommodations in Key West and Stock Island. Many boutique hotels, like The Perry Hotel and Marina or Oceans Edge, feature marina views, boat access, and even slips for those traveling by yacht. Wake up to seagulls and the clink of masts—no alarm clock needed.

Meet the Local Boating Community

Key West has a vibrant boating culture that welcomes newcomers with open arms. Join a sailing class, chat with liveaboards at the marina, or stop by one of the many yacht clubs to mingle with fellow mariners. Events like regattas and boat parades happen throughout the year, offering a chance to see the local boating lifestyle at its best.

Combine Land and Sea

Boating is only part of the Key West charm. Combine your maritime pursuits with a stroll through historic Old Town, a visit to the Hemingway House, or an evening at Mallory Square watching street performers and the sunset. Add in a food tour, a glass-bottom boat ride, or a ghost tour for a well-rounded experience.

Why Boaters Love the Keys

Key West and the surrounding Florida Keys offer a rare blend of laid-back luxury, natural beauty, and water-loving culture. From casting off on a sunset cruise to savoring freshly caught seafood from Eaton Street or heading out with Fish All In Charters, it’s an adventurer’s haven with the comforts of home port.