Key West Yacht Charter

Key West Superyacht Charter

Key West is a vibrant tropical island destination located at the southernmost point of the continental United States. Famous for its crystal-clear waters, colorful architecture, laid-back atmosphere, and rich cultural heritage, Key West offers a unique blend of Caribbean charm, historic character, and coastal beauty. Surrounded by the turquoise waters of the Gulf of Mexico and the Atlantic Ocean, the island is a paradise for travelers seeking relaxation, adventure, and unforgettable sunsets.

Known for its lively streets, historic landmarks, and welcoming spirit, Key West has long attracted artists, writers, adventurers, and visitors from around the world. The island’s charming Old Town is filled with pastel-colored homes, tropical gardens, local boutiques, art galleries, and waterfront restaurants that capture the essence of island living. Visitors can explore fascinating museums, historic sites, and cultural attractions that reflect Key West’s diverse history and maritime traditions.

The island is also a premier destination for outdoor recreation and water-based activities. From snorkeling and diving among vibrant coral reefs to sailing, fishing, kayaking, and dolphin-watching excursions, Key West offers endless opportunities to experience the beauty of the surrounding waters. Its tropical climate and relaxed atmosphere make it an ideal destination throughout the year.

Whether enjoying a sunset celebration, discovering historic treasures, indulging in fresh seafood, or exploring the stunning marine environment, Key West provides an unforgettable island escape where natural beauty, culture, and adventure come together in perfect harmony.
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The Yachts for charter in Key West

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A 44.2-metre Westship refitted in 2023, with an on-deck master, five convertible suites and an oversized fishing cockpit that turns into a beach club, chartering New England and the Leewards
TANZANITE

44M

Westship

2004

145000€

Guests

A 37.49-metre Palmer Johnson designed inside and out by Nuvolari Lenard, refitted in 2023, with two full-beam suites, a screened and air-conditioned aft deck, a hardtop sundeck with jacuzzi and
TEMPTATION

37M

Palmer Johnson

2005

80,000€

Guests

A 28-metre Tarrab refitted end to end in 2025, with a grand piano in the salon, a full-beam primary suite and a Pacific Northwest crew of three, chartering Washington, British
SUMMER SUNSET

28M

Tarrab

2002

42500€

Guests

A 2024 Ocean Alexander motor yacht offering ten guests five staterooms, a foredeck jacuzzi, sky lounge, and beach club across Florida and the Bahamas.
A SALT WEAPON

34M

2024

Guests

A 58-metre Trinity built for no-limits adventure, pairing nearly 15,000 square feet of living space with a ten-person sundeck Jacuzzi and a full dive centre.
Unbridled

58M

Trinity Yachts

2009

295000€

Guests

A 25.91-metre Hatteras refitted in 2023, with a full-beam master, a bar-led sky lounge and Starlink aboard, chartering Connecticut in summer and Florida in winter from $45,000 per week.
INDY

25M

Hatteras

2005

45000€

Guests

A 46-metre Pendennis with an elevator to every deck, a sun deck spa, a dedicated gym and one of the deepest toy inventories in her size class, chartering the West
JUBILEE

46M

Pendennis

1999

180,000€

Guests

A 44 metre Burger with a rare seven staterooms, CROSSED SABRE sleeps twelve in comfort with a sun deck jacuzzi and a full beach set up, chartering the Bahamas from
CROSSED SABRE

43M

Burger Boat

2006

175000€

Guests

A 74-metre Admiral delivered in 2018 with a certified helideck that doubles as a pickleball and basketball court, a full gym, a cinema and a spa, chartering Central America and
Planet Nine

74M

Admiral

2018

650000€

Guests

A 1966 Burger restored in 2020 to a Jack Hargrave profile, chartering the Caribbean and the US East Coast for eight guests from $48,000 per week.
SOVEREIGN

30M

Burger Boat

1966

48,000€

Guests

A 47.85 metre Christensen refreshed in 2022, LADY JOY pairs a spa-pool sun deck and a deep water-toy locker with warm mahogany interiors for twelve, chartering the Bahamas and Caribbean
LADY JOY

47M

Christensen

2007

199000€

Guests

A 39.62 metre Westport tri-deck, freshly refitted in 2024, chartering Florida and the Bahamas for up to ten guests in five staterooms from 120,000 dollars per week.
Blue Time

39M

Westport

2009

120000€

Guests

A 62-metre Andrew Winch-designed Feadship whose imaginative, art-filled interiors and light-ice capability make her one of the most characterful charter yachts afloat.
Sea Owl

62M

Feadship

2013

460000€

Guests

Highlights

Key West Yacht Charter
Key West yacht charters offer the freedom to experience the destination on your own terms. Each itinerary can be shaped around the way you want to travel, with the flexibility to move between time on the water, moments ashore and the simple pleasure of life on board.
florida yacht for charter
Tropical Island Atmosphere
Old Town’s streets are lined with wooden Conch houses built by 19th-century shipwreckers and Cuban cigar makers, painted in the soft pastels that give Key West its signature look. Duval Street runs just over a mile from the Gulf of Mexico to the Atlantic, a walk locals call going from ocean to ocean. Free-roaming chickens wander the gardens and back lanes, descendants of birds Cuban and Bahamian settlers once kept for food and cockfighting, now a fixture of island life.
florida yacht for charter
Historic Old Town
The Ernest Hemingway Home and Museum, built in 1851 from limestone quarried on site, is where the author lived from 1931 to 1939 and wrote ‘To Have and Have Not,’ the novel he set in the town itself. It was designated a National Historic Landmark in 1968. A few streets over, the Harry S. Truman Little White House served as the president’s winter retreat, one of several sites tracing Old Town’s shift from a 19th-century wrecking and cigar port into a National Register historic district.
World-Class Water Activities
The surrounding waters sit inside the Florida Keys National Marine Sanctuary, established in 1990 to protect the only living coral barrier reef in the continental United States, a reef tract that runs from Miami all the way to the Dry Tortugas. Divers and snorkelers explore sites such as Sand Key and the Eastern Dry Rocks, while the backcountry flats to the west hold tarpon, bonefish, and permit that draw anglers from around the world, especially during the spring tarpon migration.
florida yacht for charter
Spectacular Sunsets
Every evening at Mallory Square, street performers, artists, and food vendors gather for the Sunset Celebration, a tradition that took root in the late 1960s and has been run by the nonprofit Key West Cultural Preservation Society since 1984. From a yacht anchored offshore, the same sun drops behind the Gulf of Mexico without the crowds, followed by a sky that can turn green for a split second at the very last moment, the famous ‘green flash.’
florida yacht for charter
Dining & Local Culture
Key lime pie, made with the small, tart limes once grown across the island, originated here and remains the dessert every waterfront kitchen serves its own way. Sloppy Joe’s Bar on Duval Street, a Hemingway haunt since the 1930s, still draws a crowd for live music most nights, while smaller spots serve stone crab claws in season, October through May, alongside strong Cuban coffee, a legacy of the cigar makers who settled the island in the 19th century.

Key West Yacht Charter Enquire

Enquire about a Key West yacht charter to receive current yacht availability, seasonal guidance and expert insight into the cruising areas, anchorages and experiences that best fit your preferred style of charter, creating a clearer route to the right itinerary.

Key West Yacht Charter Itineraries

The Week Unfolds
Across Key West, each itinerary reveals a different rhythm, from lively ports and waterfront towns to secluded anchorages, island escapes and stretches of coastline best discovered from the sea. Together, they create a more layered way to explore, with every route shaped by the places, experiences and moments found along the way.
Coastal Maine
Seven days through Penobscot Bay, from Camden and Castine to the ospreys of Pulpit Harbor, Merchants Row and Acadia.
Southeast Alaska
Seven days from Sitka through the Inside Passage, among humpbacks in Frederick Sound, the glaciers of Tracy Arm and the totems of Wrangell.
Florida Keys
Seven days from Fort Lauderdale down the Keys, over the only living coral barrier reef in North America, to Key West and back through Biscayne Bay.
Alaska
Seven days from Juneau to Sitka, through Tracy Arm’s icebergs, the bear country of Admiralty Island and the whale grounds of Chatham Strait.
Sea of Cortez
Seven days up the Baja coast, from El Arco to the coral of Cabo Pulmo, sea lions at Los Islotes and the desert islands of Loreto.
Southern New England
Seven days from Newport to Boston, by way of Martha’s Vineyard, Nantucket cobblestones and the dunes and galleries of Provincetown.
New England
Seven days from Newport through Block Island, Martha’s Vineyard and Nantucket to Provincetown and Montauk.

Key West Must See & Do

The anchorages, experiences and places that define a yacht charter in Key West, and the ones worth building your itinerary around.
Top Anchorages

Garrison Bight Mooring Field
Wisteria Island
Boca Chica Channel
Marquesas Keys
Newfound Harbor

Top Things to Do

Snorkel the Florida Keys National Marine Sanctuary reef
Watch the Sunset Celebration at Mallory Square
Cycle or stroll Duval Street’s galleries and bars
Sportfish the Gulf Stream for marlin and tuna
Kayak the backcountry flats near the Marquesas

Top Places to Visit

Ernest Hemingway Home and Museum
Fort Zachary Taylor Historic State Park
Dry Tortugas National Park and Fort Jefferson
Harry S. Truman Little White House
Southernmost Point Buoy

Key West Charter Advices

Everything you need to know before chartering a yacht in Key West, from the best time to visit to where to drop anchor.
When is the best time to charter a yacht in Key West?

The dry season from November through April brings the calmest seas, lower humidity, and the least chance of tropical storms, making it the most popular window for chartering. Winter also coincides with the Sunset Celebration season at its liveliest and peak sailfishing offshore. Summer, June through November, is warmer and busier with local boat traffic, but also hurricane season, so many charter guests avoid August and September specifically.

What's the closest airport for flying into Key West?

Key West International Airport (EYW) sits about two miles from Old Town and takes commercial flights from several Florida and East Coast hubs, plus private aircraft. Many guests instead fly into Miami International Airport and drive the Overseas Highway, a roughly three-and-a-half-hour, 160-mile route across more than 40 bridges connecting the Keys, considered one of the most scenic drives in the country.

Where are the best spots to anchor near Key West?

Wisteria Island, just off the harbor entrance, is the most sheltered option close to town and a short tender ride from Duval Street. For a wilder setting, the Marquesas Keys sit about 25 nautical miles west, a ring of mangrove islets around a shallow lagoon best visited in settled weather. Boca Chica Channel toward the Lower Keys offers a quieter alternative with easy access to the backcountry flats.

How many days should we plan for a Key West charter?

Three to four days covers Old Town, the reef, and a full day trip to Dry Tortugas National Park, 70 miles west of Key West, which needs calm conditions and a long weather window since it has no safe harbor for shelter. Guests who want to add the Marquesas or push further into the backcountry flats for fishing typically extend to five or six days.

Can we take the yacht all the way out to Dry Tortugas National Park?

Yes. Dry Tortugas has no marina and no fuel dock, so yachts anchor off Garden Key near Fort Jefferson and go ashore by tender; no National Park Service permit is required for private vessels, unlike some Western parks. The crossing is about 70 miles each way across open Gulf water, so captains typically wait for a settled forecast and plan an overnight anchorage rather than a single-day round trip.

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