Who We Are:
Captain Joy turned her passion for sailing into a business almost 20 years ago. Her mission is to give her customers a peaceful, joyful and harmonious experience with the sea and each other―always with safety in mind.
Sailing trips, open spots, and stories—straight to you.
Freedom Feels Better at Sea
Celebrate America’s 250th birthday aboard a private coastal sail—featuring a welcome toast and stories of Connecticut’s maritime past along the way.
-
The Freedom Sail – Simple, private, and entirely your own
-
250 Coastal Heritage Sail – A relaxed sail with stories of Connecticut’s maritime past
-
Sunset Freedom Sail – End the day on the water with a quiet, celebratory sail
Summer and sunset dates are limited. Reach out with your preferred date and sail style, and I'll help you plan the perfect outing on Long Island Sound.
All Sails - Bring up to 4 guests for one flat rate of $575. Additional guests are $125 each, up to 6 total passengers.
Mention "Freedom" when booking and receive $25 off your private charter.
Sail Connecticut
Sailing Long Island Sound
Sail along Connecticut's beautiful shoreline with family and friends aboard a private charter.
Whether you're celebrating a birthday, anniversary, retirement, marriage proposal, family gathering, hosting out-of-town guests, or honoring a loved one with a memorial at sea, each sail is tailored to your occasion.
Bring up to 4 guests for one flat rate of $575. Additional guests are $125 each, up to 6 total passengers.
Mention "Freedom" when booking and receive $25 off your private charter.
Sail International
![[000567]_edited.jpg](https://static.wixstatic.com/media/3038b9_07ec77a3e829479f80eed7c3e7dfcef5~mv2.jpg/v1/fill/w_7,h_5,al_c,q_80,usm_0.66_1.00_0.01,enc_avif,quality_auto/%5B000567%5D_edited.jpg){kind=small}
Reviews From Our Travelers
Joy came through for us! Would highly recommend her for your delivery. She also provided instruction underway which was invaluable.
Book a cabin on a fully crewed yacht.
Book solo with us, enjoy the safety and structure of group travel. Meet a bunch of new BFFs along the way.
