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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. If you’re looking for more of an adventure, we can show you the cliff-jumping spots that only locals know. 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.

The Bahamas 

Custom week-long island excursions in the Bahamas available on request. 

New England

Best Times: June - September


During the summer, you can find us mainly around the Block Island area booking the boat on Airbnb. We are providing customized experiences for overnights, dinner cruises, day sails, or whatever your group is looking for.

If your party wishes to explore and sail around the New England area, we also offer custom week-long excursions.

A complimentary breakfast is included with your overnight stay, and drinks and snacks are included for day sails.

Offshore Experience 

This trip is designed for anyone looking for opportunities to learn how to sail, build miles on a larger vessel, or just to experience an offshore voyage. Kai will be provisioned with food and drink upon your arrival. All customs and immigration fees and lodging are covered by Kai with arrival to Bermuda and USA. During the trip, you will be acting crew, which means you will participate in a 3-hour watch rotation for 24 hours a day. Everyone will pitch in with cooking, cleaning and general boat chores that are needed along the way. Come ready to work hard, play harder and experience a trip of a lifetime. There is no experience needed —  just a good attitude.
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