Sail Watch Hill:For travelers who use our online itinerary creator, Westerly holidays become easier to arrange, with trips to the Sail Trim Again and other attractions mapped out and timetabled.
Departing Watch Hill, RI, Captain Jack Spratt offers his historic classic wooden Sailing yacht "TRIM AGAIN" for private Two (2) Hour Day or Sunset Charter.
Learn to sail a traditional wooden gaff sailboat. 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.
Lighthouse Tours, Historic Harbor Tours & Seal Watch, Birding or photography excursions to the Islands or Hamptons:
We offer a variety of programs listed here or we can create an excursion specifically to your needs. Perhaps a two hour tour of the NY, CT & RI shores, a half day excursion stopping for lunch at a seaside lobster shack, a sail into Mystic Seaport and private behind the scene tour by Captain Jack, a romantic sunset sail with your music playing in the background while you sip sparkling wine, a sailing lesson, seal watching or an excursion to a nearby island.
Sail Trim Again reviews
My husband, 12-year old daughter, a friend of hers and I joined Capt. Jack for a 3-hour tour in late July. When we travel we always enjoy learning more about the history and architecture. This is... more »
Captain Jack and his beautiful boat made our Watch Hill visit one for our memory book. The boat was impeccably taken care of and Cap’t Jack made sure everything was in compliance with Covid measures..... more »
An amazing experience on the Trim Again. Captain Jack is a nice guy and knows the local history extremely well. Beautiful boat with an amazing ride on the skipper's model T afterwards. Perfect honeymoon activity. Highly recommended.
When in Watch Hill you MUST charter a trip on Trim Again with Captain Jack. It's time very well spent as nothing recharges your batteries more than a quiet sail in the bay and out to Fisher's Island on Trim Again. Captain Jack is an encyclopedia of local knowledge and he's happy to provide a guided tour. But if you want some islandy music or a quiet cruise, he's happy to accommodate that too—he did for us. No trip to Watch Hill is complete without getting out on the water and Trim Again is the best way to do it. And it's surprisingly affordable as well. Give Captain Jack a call, you'll be very glad you did.
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