The best boat ride I have had ever!  W.E

The Mission of Sail Trim Again is to enrich guest experience through historical, nature & environmental tours aboard classic wooden sailing & motor yachts.

 Sail TRIM AGAIN  & Motor Yacht ENCORE

  Cruises, Adventures, Historical Tours

      Romantic Sunset Cruises- Learn to Sail -Water Taxi 

    Two hour, Half and Full Day Private Excursions

The best part of our stay at the Ocean House was sailing Trim Again. SJM



Captain Jack Spratt offers his historic classic wooden Sailing Catboat Yacht, TRIM AGAIN, for private two (2) hour, three (3) hour day sails, sunset sails, moon light sails, and half & full day excursions. Everyone is encouraged to sail the boat. Capt. Jack will tell you about the interesting people and history of the area. Interested in a family gathering? TRIM AGAIN is the perfect venue for a romantic date, anniversary, engagement, intimate wedding, or a sunset sail with sparkling wine!  Interested in learning to sail?  Capt. Jack makes it fun, informative and relaxed. 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.

2 Hrs



Sunset 2 Hrs

$600 (includes sparkling wine)

Catering available


"Thank you for a beautiful evening- the perfect ending to an incredible holiday. The sunset was indescribably amazing." Emma


A classic wooden Motor Yacht

"Jack, thank you so much for a truely stunning and informative evening tour. It was the highlight of our trip to the east coast and Ocean House." Brooke

Come aboard Capt. Jack's stunning, beautiful and fast motor yacht, ENCORE, for historical three-state lighthouse, mansion, wildlife tours of historic harbors; Watch Hill, RI, Stonington, CT and Fishers Island, NY, sunset cruise, romantic cruises, full & half day excursions.  Captain Jack provides unique insights regarding the region's history, wildlife and those who make a living from these shores.

We offer a variety of programs listed here or we can create an excursion specifically to your needs. Perhaps a two- or three-hour tour of the NY, CT & RI shores, a half day excursion stopping for lunch at a seaside lobster shack, a full day charter and private tour with Capt. Jack to Mystic Seaport Museum, a romantic sunset sail or motor yacht cruise with your music playing in the background while you sip sparkling wine, seal watching or an full day excursion to a nearby islands, historic places and towns. Or a full day trip to the Hamptons, or Newport, or Block Island, or Historic New London (Submarine Base, Coast Guard Academy, Electric Boat Submarine contractor, Revolutionary War forts.)


Two (2) Hour:   $500


Sunset 2 Hrs: $600 (includes sparkling wine) 

Catering Lunch available St. Clair's a Watch Hill Insitution


ENCORE Historical 3 State, Lighthouses, Mansions Adventure

Beautiful Yachts

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, marriage vows, birthday, anniversary, or retirement are perfect while aboard 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.


Experiences in Pictures


Visit us right in the village of Watch Hill, RI - a very short walk from the Ocean House.  We have one free parking space at our floating dock.