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Sail the Caribbean and Beyond. Every itinerary is customized to your interests, the weather and your sense of adventure.
CURATED ITINERARIES.
UNLIMITED POSSIBILITIES.
Monohull Sailing Charters
Eastern Caribbean
Eastern Caribbean Monohull sailing is a little different than exploring the Virgin Islands.
Starting as far north as St Martin and ending in Granada, the islands of the Lesser Antilles offer beautiful mountain landscapes, jungles, hot springs and the opportunity to experience true "blue-water" sailing. During a charter in the Eastern Caribbean you could climb Petit Piton in St Lucia, explore rainforest and waterfalls of Dominca, or relax on the white sands of the Grenadines.
Inquire for specific locations and routes through the island chains.
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The Leeward Islands
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US Virgin Islands
Best Times to Visit: December - May
For American citizens, one of the most alluring factors in chartering in the US Virgin Islands is their status as a territory - no passport required! The islands’ pristine waters are perfect for snorkeling, diving and fishing, and their beaches are just right for relaxing or sipping a cold drink at a beach bar. On land, you can hike well-maintained trails in the Virgin Islands National Park on St. John, explore the shopping scenes of Cruz Bay, Christiansted and Historic Frenchtown and sample all the diverse cuisine the islands have to offer!
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British Virgin Islands
- ONLY 3 Weeks Available 2025/26
Best Times to Visit: December - May
A trip to the BVI starts in St. Thomas, USVI where you will board Kai before we embark on our favorite "loop" around these mountainous islands. Beginning with a trip to Jost Van Dyke and the infamous Foxy's and Soggy Dollar in White Bay, we contiue to Sandy Spit for swimming and snorkeling or head right across the channel for happy hour on Cane Garden Bay in Tortola. The next few days are generally spent exploring the baths in Virgin Gorda, fire-cooked lobster on the beach in Anegada, and snorkeling the famous reef 'The Indians' at Norman Island.
*BVI charters are limited by our permit restrictions, book soon to secure your trip!
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Spanish Virgin Islands
Best Times to Visit: December - May
The Spanish Virgin Islands just began welcoming charter boats in 2020. These are the least-traveled islands around the VI and some of the most beautiful. From iconic white sand beaches with palm trees — including one of the world’s top 10 beaches, Flamenco Beach — to some of the world’s best snorkeling, the Spanish VI have so much to offer. We can also make a couple of stops around Culebra, a beautiful sleepy island off the coast of Puerto Rico. Your footprints will be the only ones on some of the beaches there. Culebrita, a protected island, offers a pristine white sand beach, bubbly pools, sea turtles and beautiful palm trees to relax beneath.
New England
Now Booking Summer 2027!
Discover New England the way it was meant to be explored—from the deck of a classic sailing yacht!
Explore the rugged coast of Maine, Cape Cod, the Elizabeth Islands, Montauk, and Block Island. Visit historic Cuttyhunk, Nantucket, Martha’s Vineyard, Provincetown, and countless historic waterfront towns. Start cool mornings with a crackling woodstove and hot coffee, spend your days swimming, exploring, or relaxing on the water, and end them with the best of New England seafood—lobster, just-shucked oysters, sweet clams, mussels, scallops, and classic clam chowder. In one of America’s great sailing regions, there’s no better way to experience New England than in the comfort, freedom, and style of a private yacht.
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Offshore Experience
Available By Inquiry
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