Private Charters


Private Charters include 2 hour, 3 hour, 1/2 day and full day excursions. Catered picnic lunch, wine & cheese, or elegant diners are available through our exclusive relationship with Ocean House.


Charter Ideas


Learn to sail a classic gaff rigged wooden catboat: Enjoy learning knots, rig handling, points of sail, traditional navagation


Sunset: We have some of the most beautiful sunsets in the world.


Saltwater Farm Vineyard Tour from the Sea:


Capt. Jack will pick you up in front of the Ocea House in his 1913 Model T woody wagon and give you a tour of Watch Hill. Arriving at the Watch Hill Docks you will Climb aboard Trim Again, a classic sail boat and enjoy the  peaceful ride with our sails up or down, your choice. We anchor off of the remote and exclusive Elihu Island and row a classic pulling boat a few hundred yards to the beautful and exclusive Saltwater Farm. You will walk through this amazing vineyard and into the 1930's converted airplane hanger for a tasting. This tour is a half day and includes fees for the vineyard your and tasting and the vintage boat ride


Bird watching: While ghosting along the shores of Barn Island learn about the amazing variety of water birds that live or transit this area known as the North Flyway. Captain Jack will describe bird behavior in courtship & rivalry.


Mystic Seaport Museum: sail or motor to the American Museum of the Sea aboard one of Mystic Seaport Museum best known boats Trim Again or ENCORE. Enjoy a private behind the scenes tour of the Museum provided by Captain Jack, a life member and volunteer of Mystic Seaport.


Light House Tour:  Encore only - visit 9 to 10 light houses and two life saving stations. Learn about shipwrecks and hurricanes.


Oyster Farm Tours:  ENCORE, learn about how oysters are farmed as well as harvested.


Special Occasions: Engagement, birthday, anniversary, milestone with flowers, sunset or moonlight cruises. Perhaps sail to a private anchorage, swim, snorkel, enjoy lunch or dinner aboard this beautiful classic yacht.


Moonlight Charter: adults only


Harbor Seal Tour:  Spring and Fall only

Treasure Hunt

Treasure Hunt


Catering, wine, drinks and flowers seperate charge. Children must be age appropriate. We like to keep the experience very special and limit the number of quests to 6.  Children under 5 are inappropriate for sailing charters but are fine for Motoryacht charters at the descretion of the Captain for their health and safety reasons. Please call Capt. Jack to discuss children under 5.


Call  Capt. Jack ahead so that we can plan the perfect half or full day charter. 860-227-2339