Sailing Day & Sunset Charters

Sailing Day & Sunset Charters

Let’s Go Sailing

Relax while sailing the waters of Watch Hill, Fishers Island and Block Island Sounds on a two-hour tour. A storyteller at heart, Captain Jack Spratt shares the history of this special area, its unique geology forged by glaciers, the remarkable story of the people, and fascinating historic events. Interested in a sailing lesson? Captain Jack provides the opportunity to sail the gaff-rigged classic catboat. Participate as much or as little as you wish.

Champagne Sunset Charter

Uniquely situated, Watch Hill experiences both beautiful sunrises and sunsets over the water. The sunsets are especially breathtaking and never disappoint. Coast along, under sail alone, on a wooden yacht noted for her beautiful varnished finishes, listening to your favorite music through her wooden hull as the sun sets, a truly romantic experience!


Trim Again offers four tours a day and departs from Maxon Dock in Watch Hill, a three-minute walk from the Ocean House. Proceeds from all Trim Again charters benefit the Mystic Seaport Museum.


Two-Hour Day Charter: $400 (plus 18% gratuity)*
Two-Hour Sunset Charter: $500 (plus 18% gratuity)
Half-Day Cruise: $800 (plus 18% gratuity)
Full Day Cruise: $1200 (plus 18% gratuity)

*Each additional hour is $175.


Light snacks, non-alcoholic beverages, captain, harbor and fuel fees. Sunset Charter also includes a bottle of champagne and cheese plate for two.

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