Kai and her crew - Captain Justin and first mate Sarah- are looking to have YOU stay aboard. Live somewhere cold?? Get away this winter for a warm relaxing week in the Caribbean! You can find Kai hanging out in the US & British Virgin Islands. The Spanish Virgin Islands is NEWLY ADDED to places we can charter as well!! Our specialty is offering week long charter vacations for parties of up to six. During your stay, we will sail from island to island and see all the wonders each has to offer. The boat is a 72 foot classic sailing vessel with ample space for relaxing, lounging, and living. If you want to know more, check out our destination page and rates for more info and photos of her beautiful features.  

Chartering Kai


If you have found yourself reading this, then vacationing on a classic sailing vessel must be something that interests you! Trust us, she wants to take you on the waters...whether it be your first trip or your 12th time to revisit! Kai travels between New England in the summer, and the Caribbean in the winter time. On Kai, we can show you the regular hot spots, or take you to a secluded anchorage on your private beach. We love it all, and want to bring you to whatever place it may be!


Come play with us!!


            3 Cabins    

      2 Heads

 Spacious deck with

     bean bag chairs

 Stand up Paddle boards

2 Single Kayaks

Snorkel Gear


Two luxurious seating areas in the salon

  Covered cockpit with full wind and rain coverage

The past few years we have been migrating North on Kai after hurricane Irma and Maria hit the US &  BVI hard in 2017. We have found ourselves making our way through the Bahamas many times, leaving us with a deep love for the Bahamas.

   After watching Dorian wipe away so many homes, friends, and memories we decided going to bring supplies was something that we had to do! After living through and experiencing the aftermath of two Cat 5 hurricanes back to back, we came up with an extensive list of supplies. 

  We loaded thousands of pounds of supplies, shoved them in all knocks and crannies of the boat and headed to the Abacoes of the Bahamas. The supplies were all raised by local CT organizations-  home town school foundations, and a Gofund me account and through our social media pages.. "Green Turtle Key Relief Vessel" 

  Our supplies consisted of 18 5 gallon buckets of elastomeric paint, every 2" nail in Lowes and Home Depot, tarps, clothes, tools, 50 pound bags of rice, Mountain House meals, water, and many other odds and ends. 

Giving back to this community, no matter how small, filled the hearts of our crew and those we were able to give back to. Thanks to everyone involved- from donating, loading, sailing there, and everything in between. It will be forever in our hearts. 

Whats new on KAI??

Giving Back To The Bahamas

@2018 Charter Kai LLC