All-inclusive captained charters, live-aboard yacht stays & private events in the Southernmost City in the USA.
Live your dream of sleeping out on the ocean in a luxury cabin cruiser. Two staterooms each with queen beds, two full bathrooms, covered patio, AC, satellite WiFi, full indoor & outdoor dining. Anchored on the ocean — see dolphins, turtles and manatees right from the boat! Round-trip water shuttle to Key West available sunrise to sunset.
Perfect for you and up to 10 friends — get to the sand bar, snorkeling, sunset cruise, scuba, fishing or whatever your heart desires! Private captain and crew, all gear, floats, ice, coolers, catering and open bar always included.
Your private shuttle boat to-and-from the yacht on anchor! Enjoy both the island of Key West and the open sea during your "on the hook" getaway.
From remote sandbars to Civil War forts — every charter is a new adventure.
Accessible only by boat — white sand beaches, ankle-deep water, massive party! Visit Snipe Point, Jewfish Basin, Mud Key & more!
The most famous part of Key West — classic restaurants like Schooner Wharf and Conch Republic, and the biggest yachts at Key West Bight Marina.
A famous pre-Civil War National Historic Monument with gorgeous beach, deli, picnic tables and the best views in Key West. A can't-miss National Park.
The southernmost island in the United States — accessible only by ferry. Be sure to book the resort at Latitudes in advance!
The last stop before the open channel to Dry Tortugas National Park. Empty beaches, turquoise water, even dolphins. Last spot with cell service before Fort Jefferson!
The gem of the Florida Keys and Lower Caribbean — Fort Jefferson is a Civil War-era fortress. Lighthouse Key and Windjammer Wrecks are also must-sees.
Only 7 miles due south of Key West — snorkel or scuba dive the ruins of an old island dock and lighthouse with thousands of fish and wildlife.
The Sea Cow — nature's gentle giants. Cruise through covered mangrove canopies to find herds of these friendly ocean cattle.
The most famous event in Key West — every evening at sunset at the southernmost place on earth with street performers, vendors and a free festival.
The home of Ernest Hemingway, Key West's own literary celebrity. Guided tours and endless six-toed cats!
A magical indoor terrarium full of thousands of butterflies, flamingos, birds, and a gorgeous tropical botanical garden — a Key West local secret!
The most southern point in the continental USA. Lines form for pictures so go early! Visit the nearby Southernmost Mansion for rich Key West history.
This key was split in two when a Navy Destroyer tore through it — creating a spectacular protected reef and beach for snorkeling and BBQs.
The most famous commercial strip in Florida — one mile from Gulf to Atlantic, lined with live music, outdoor restaurants, street vendors and all the vibrant colors of Key West!
Upgrade your Key West "on the hook" vacation with gear, food delivery, a private chef, and more. Available with 12-hour notice so everything is ready when you arrive.
See All Add-OnsBrowse the Key West live-aboard yacht gallery.