"The best part of our stay at the Ocean House was sailing

Trim Again." SJM

The Mission of Sail Trim Again; to enrich guest experience through historical, nature and environmental tours and Romantic moments for a lifetime of memories aboard  Historic sail & motor yachts, TRIM AGAIN & ENCORE.

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

PRIVATE Classic Sail & Motor Vessel Charters out of Watch Hill 


 Historic Catboat Sailing Yacht 

1.5 Hour, Half & Full Day Pivate Excursions  

      Romantic Sunset Cruises- Learn to Sail 



Captain Jack Spratt offers his historic classic wooden Sailing Yacht, TRIM AGAIN, for private (just you & your guests), two (2) hour, three (3) hour day sails, sunset sails, moon-light sails, and half or full day excursions for up to six guests. 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.

1.5 Hrs


Sunset 2 Hrs

$600 (includes sparkling wine)

Catering available



Capt. Jack offers 2 hour (day & sunset) charters. 3 hour cruise, with a stop for lunch at a seaside restaurant. A half or full day excursion aboard the historic ocean capable swordboat ENCORE. Historical tours of the islands, lighthouses, mansions and villages, passing through three states!  Enjoy a family boat cruise or a bachelorette party, engagement, spectacular sparkling wine sunset cruise. Harbor seal and migrating bird adventures in the spring and fall. Trips to Montauk ( for lunch) , East Hampton, Sag Harbor, Block Island, Mystic, Stonington, Pawcatuck River (named a Wild & Scenic River), Historic Thames River ( home to the U.S. Sub Base, U.S. Coast Guard Academy, Revolutionary War Forts), Harvard-Yale Rowing Regatta ( Capt. Jack rowed varsity for Cornell (All Ivy) and team USA and coached rowing at the U.S. Coast Guard Academy offering insight and history of the regatta), Newport (jazz festival, Victorian Mansion tour). Water taxi service for golfers lucky enough to play  Fishers Island famous golf course. Choose half or full day excursions and Capt Jack will develop a custom itinerary that could include Jack giving you a guided tour of Mystic Seaport Museum, Block Island, Historic Stonington, Sag Harbor, Newport. Capt. Jack is a recognized local historian, is historical articles appear in local media, including the Ocean House and Weekapaug Inn Magazine, Hill, Pond & Preserve/ Stroll magazine. Jack and his yachts have appeared in local  documentaries, local TV news and television shows including, This Old HouseBeachfront Bargin Hunt, fashion magazines and in the movie Hope Springs. 

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.)


1.5 Hour:   $500


Sunset 2 Hrs: $600 (includes sparkling wine) 

Catering available; Ocean House,  St. Clair's, Sandy's, Misquamicut Sandwich


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.