Custom Experiences Ideas

Private Charters include 2 hour, 3 hour, 1/2 day and full day adventures and yacht excursions. Catered picnic lunch, wine & cheese, or elegant dinner for two (2) are available for Ocean House, Watch Hill Inn, Weekapaug Inn and the Ocean House Cottage Collection guests through our exclusive relationship with Ocean House.


Excursion Offerings:



Learn to sail a classic gaff rigged wooden catboat or a 1923 classic racing sloop

Learning knots, boat handling, points of sail, navagation, anchoring, passage planning


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


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.


New London Coast Guard Academy, Revolutionary War Forts, Naval Sub Base, Electric Boat Submarine builder.


The Hamptons, Sag Harbor, Montauk, East Hampton, Shelter Island, Greenport.


4th of July Fireworks of the Ocean House


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


Special Occasions: Engagement, birthday, anniversary,  we do small intimate on board weddings, 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


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