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: $450 (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.


May through October:

• Cruises depart daily, based on availability, from Maxon Dock

Suggested Dress

Casual, non-slip shoes, and a warm jacket for evening cruises

Cancellation Policy

• 48 hour cancellation required to avoid cancellation fee
• Cancellations within 24–48 hours of departure: 50% of cruise fee
• Cancellations within 24 hours of departure: 100% of cruise fee
• Cancellation fees can be credited towards a future booking
• Cancellations due to weather (as determined by Captain 30 minutes prior to departure) are fully refundable