Sail Trim Again, Watch Hill

#4 of 6 in Outdoors in Westerly
Sail Watch Hill:

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.
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.
Create an itinerary including Sail Trim Again
© OpenMapTiles © OpenStreetMap contributors
Sail Trim Again Reviews
Rate this attraction
TripAdvisor Traveler Rating
TripAdvisor Traveler Rating 5.0
56 reviews
  • My wife and Rose and I had the pleasure of taking the last Sunset Cruise of 2019! We were originally scheduled to sail in mid September but had some scheduling issues and could not make it. Captain...  more »
  • Captain Jack took my husband and I out on a 2-hour romantic sunset cruise while we were on our honeymoon in Watch Hill, RI. It was the perfect evening. Captain Jack is extremely kind and is the best.....  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.

Plan your trip to Westerly

  • Get a personalized plan

    A complete day-by-day itinerary
    based on your preferences
  • Customize it

    Refine your plan. We'll find the
    best routes and schedules
  • Manage it

    Everything in one place.
    Everyone on the same page.

Side trips from Westerly

Duration:2 h 30 min
Duration:2 h

Hidden gems in Westerly

Duration:2 h

Kid-friendly things to do in Westerly

Duration:2 h
Duration:2 h
Duration:2 h
Duration:2 h

Nearby attractions in Westerly

Duration:2 h
Duration:1 h 30 min

Parks in Westerly

Duration:2 h