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Ocean House > Activities > Yachting


Experience the natural beauty of our coastline aboard our classic motor and sailing yachts. From late May to early October, the Ocean House offers cruises aboard three extraordinary and very different boats. Located a mere three-minute walk down the hill from the Ocean House, the fleet offers many ways to enjoy the water.


Built in France by Latitude 46, a company known for classic design, high styling and impeccable construction, Dandy, an Andreyale 33, was inspired by the American commuter boats of the 1930s. As the primary member of the Ocean House fleet, Dandy provides the ideal atmosphere for half- or full-day charters, cocktail or dinner cruises. Her roomy cockpit and vast salon with satin mahogany finish offer ample and elegant accommodations for 4–6 guests plus crew. Whether anchored in the harbor or bay or cruising in the open ocean, Dandy’s shallow draft allows for exploration to remote and secluded destinations, making your cruise unique and unforgettable. 

Trim Again

Go back in time to when the historic “party” Catboat charters, popular in the Golden Age of Watch Hill, sailed off the docks of Watch Hill Cove, just a stroll down the hill from Ocean House. Trim Again, a classic Catboat Yacht with a generous 11’3” beam, is varnished to perfection and roomy enough for 4–6 guests plus crew. Her large cockpit makes her ideal for romantic sunset cruises, nature tours, lighthouse tours, learn-to-sail excursions and special occasions. With vast experience and local knowledge, Captain Jack Spratt has access to special places not available to the general public. Captain Jack donates his charter fee to support the Mystic Seaport Museum. 


Encore is a repurposed and restored sword fishing boat. During Prohibition, rum runners were sea-worthy fishing vessels that were re-powered to out run the Revenue Cutter Service, today’s Coast Guard. Encore was originally built for long fishing voyages in the rough Atlantic Ocean. Owner and captain, Jack Spratt saved the boat from the scrap yard and engaged the well known wooden yacht restoration team of Taylor & Snediker to restore and repurpose her as a very fast seaworthy motor yacht. Encore is only available for the speciality cruises listed under Area Yacht Tours