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Caribbean Monohull Sailing Charters

US Virgin Islands

Best Times to Visit: December - May

The US Virgin Islands can give you a taste of the Caribbean without ever having to leave the 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 on a cold drink at a beach bar. On land, you can hike well-maintained trails in the Virgin Islands National Park on St. John, or check out the shopping scene on the islands. 

British Virgin Islands

Best Times to Visit: December - May

If you want to explore the BVI, you’ll board Kai in St. Thomas, USVI 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. From there we can mosey 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, lobstering in Anegada, and snorkeling the famous The Indians at Norman Island.

Spanish Virgin Islands

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.

Eastern Caribbean        Monohull Sailing


Eastern Caribbean Monohull sailing is a little different than the Northern Leeward Islands. This trip is much more sailing and can require a strong stomach and love for sailing. This trip will bring you too many different islands. Starting in St Martin and ending in Granada. On this sail you can climb petit piton in St Lucia, explore rainforest and waterfalls in Dominca, and relax on the white sands of the Grenadines. 

inquire for specific locations and island chains. 

New England

          Currently Unavailable 


Offshore Experience 

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