Private two hour, half or full day sail (for you and your guests)  aboard the Classic Wooden sailing Vessel TRIM AGAIN - We limit guests to six (6) for an intimate experience. All charters are PRIVATE.


TRIM AGAIN has been in movies, fashion magazines and has witnessed numerous engagements, family gatherings, anniversaries and romantic dates. Couples, business groups, brides maids have created life long memories enjoying the natural beauty of the area aboard this incredible yacht.    


TRIM AGAIN is the perfect sensual yachting experience. From her exquisite varnish finishes, brilliant shining nickel-plated hardware, and large wooden spars to her massive sail, this wooden boat sails, smells and sounds like nothing you have ever experienced. Her majestic Sail shades the cockpit and her kind sailing characteristics (she does not heel over) and shallow draft provide access to remote and special places throughout the seashore. Step back in time to the peak of Watch Hill's Victorian Hotel and Cottage Colony era of Catboat party boat tours sailing on the Bay, Fishers Island Sound, River and Ocean. A founding member of the Catboat Association, Trim Again has been described as the ultimate Catboat Cruising Yacht. At 24' by 11'3" she is a large and original wooden Catboat. Built for a wealthy coffee merchant (Victor coffee) no expense was spared in her construction, materials and maintenance. Her galley is stainless steel (a gift from Howard Johnson). Trim Again's decks are of teak, her cockpit and house combings of steam bent oak, and her cabin sole finished in teak with interior trim of teak and mahogany. She is finished to perfection, varnished inside and out. In 2009 her bottom was refastened with 1,350 Monel fasteners (screws) at a cost of $4.10/ screw to ensure her life span would exceed 100 years!


A fixture in Watch Hill for 30 years her Master and Captain, Jack Spratt offers a very special and unique experience. With her large cockpit, Trim Again is ideal for 4-6 guests for 2 hour, half and full day sails, sunset cruises.


Sunset - Moon light Sailing - Harbor Tours- Excursion to Fishers Island

Learn to Sail-  Nature Cruise 
Engagement- Anniversary- Birthday


Catboats lined both sides of Watch Hill and Plimpton Docks during the peak years of the Ocean House, Larkin House, Plimpton House, Watch Hill Inn from 1890 - 1929. Captains would leave sails up to dry in the morning breeze and wait for hotel guests to arrive for a day aboard these "party boats". Women would be in dresses, men in jackets and ties. They would sail the bay and up along the Pawcatuck River. As they did not have power they often arrived late back to the dock.


Dodging Steamships was something of a sport  that came to Watch Hill from Stonington and Westerly often resulting in harsh words exchanged between Steamboat and Catboat Captains and at times fights on the dock.