"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


Painting Ghosting Trim Again

..."the best part of our trip was chartering a sail boat on Saturday afternoon.  We chartered the boat 'Trim Again' for two hours.  We were picked up by Jack Spratt (owner of 'Trim Again' and our captain) in his very own Model T Ford.  When he heard that it was our first time in Watch Hill, he gave us a tour of the area on the model T before heading to the sail boat..."

By request Capt Jack will provide pick up and drop off to Ocean House as well as a land tour of Watch Hill Capt Jack's 1913 Model T Ford Depot Hack

Sail Trim Again or Charter ENCORE


In partnership with the Ocean House Resort in Watch Hill, Rhode Island, Captain Jack Spratt offers his historic classic wooden Catboat yacht "Trim Again" and his repurposed swordfish motor yacht "Encore" for historic tours of Watch Hill, RI, Stonington, CT and Fishers Island, NY, sunset charters, sailing, and motor excursions departing Watch Hill. Captain Jack provides unique insights regarding the region's history, wildlife and those who take a living from these shores. Climb aboard 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