"A real sea adventure with nostalgia and style! Captain Jack and his TRIM AGAIN is a beacon of light to the history of Watch Hill and a found treasure to all who want to experience  an authentic sea worthy path." Robert & Bonnie Vontell


S/V TRIM AGAIN ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ M/V ENCORE

..."the best part of our trip was chartering a sail boat on Saturday afternoon.  We chartered the boat 'Trim Again' for two hours."

Painting Ghosting Trim Again

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Sail Watch Hill: Classic Sailing & Motor Yachts

Departing Watch Hill, RI:

Captain Jack Spratt offers his historic classic wooden Sailing yacht "TRIM AGAIN" for private Two (2) Hour Day or Sunset Charters. Learn to sail a traditional wooden gaff sailboat. Spend a relaxing day on the water with a half or full day charter on this beautiful wooden yacht in the calm waters of the bay.


Lighthouse Tours, Historic Harbor Tours & Seal Watch, Birding or photography excursions to the Islands or Hamptons:


ENCORE Motor Yacht:

Come aboard Capt. Jack's repurposed swordfish motor yacht "ENCORE" for historical tours of Watch Hill, RI, Stonington, CT and Fishers Island, NY, sunset charters, excursions departing Watch Hill. Captain Jack provides unique insights regarding the region's history, wildlife and those who take a living from these shores.


Enjoy the luxury of these special yachts and spend a few hours relaxing, reacquainting with a loved one, family or friends.



Special occasions such as an engagement, birthday, anniversary, retirement are perfect while sailing the gaff rigged "TRIM AGAIN" or the beautiful 700 HP wooden motor yacht "Encore". Captain Jack has a well-deserved reputation for making these excursions very special and memorable.


We offer a variety of programs listed here or we can create an excursion specifically to your needs. Perhaps a two hour tour of the NY, CT & RI shores, a half day excursion stopping for lunch at a seaside lobster shack, a sail into Mystic Seaport and private behind the scene tour by Captain Jack, a romantic sunset sail with your music playing in the background while you sip sparkling wine, a sailing lesson, seal watching or an excursion to a nearby island.


Visit us in Watch Hill, RI or contact


Captain Jack Spratt 860.227.2339