THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel
Discover the charm of Watch Hill aboard the classic Wooden Yacht TRIM AGAIN, with private morning, afternoon, or sea breeze sails that suit every sailor’s pace and preference.
Discover the charm of Watch Hill aboard the classic Wooden Yacht TRIM AGAIN, with private morning, afternoon, or sea breeze sails that suit every sailor’s pace and preference.
Book with Sail Trim Again
Verified experiences and guided adventures in the surrounding area.
Operated by Sail Trim Again · Westerly, Rhode Island
easy.
2–3 hours.
Suitable for most fitness levels; ability to move comfortably on deck is recommended
No sailing experience is required; the crew provides guidance and training, making it enjoyable for beginners.
Yes, each sail is private and customizable to accommodate groups, couples, or solo travelers.
We recommend bringing layered clothing, sunscreen, sunglasses, a hat, and any personal seasickness remedies.
Guests are welcome to bring their own snacks and non-alcoholic beverages; alcohol policies can be discussed during booking.
Trips may be rescheduled or canceled for safety reasons, with full communication provided prior to your sail date.
Yes, children accompanied by adults are welcome, but all guests must be able to safely board and move about the yacht.
The Wooden Yacht TRIM AGAIN is a classic vessel, preserving traditional sailing craftsmanship dating back decades, tied to Rhode Island’s rich maritime heritage.
Sail Trim Again supports local marine conservation efforts by promoting responsible boating practices and protecting coastal ecosystems.
Sail Trim Again is a Westerly, Rhode Island-based charter operator offering private sailing and motor-yacht experiences around Watch Hill and Fishers Island Sound. Operating classic vessels such as the wooden yacht TRIM AGAIN and the historic motor yacht ENCORE, the business provides a range of options including short morning or afternoon sails, romantic sunset cruises, and multi-hour sightseeing tours. Trips are designed for a variety of guests: beginners seeking a peaceful sail, couples celebrating special occasions, families looking for wildlife and coastal views, and history enthusiasts interested in local landmarks. TRIM AGAIN hosts serene morning, afternoon, or sea-breeze sails that emphasize the classic wooden-yacht experience. ENCORE offers sightseeing, historical and wildlife tours, including a two-hour tri-state tour and a three-hour tour with a lunch stop at a seaside clam and lobster shack. All offerings are private charters tailored to the group's preferences and occasion. Sail Trim Again highlights the scenic coastline, lighthouses, and wildlife of the Watch Hill, Stonington, and Fishers Island area while providing thoughtful, hospitality-focused outings. The business is anchored in local knowledge of Fishers Island Sound and Watch Hill waters, delivering safe, memorable marine experiences from Westerly, Rhode Island. For those seeking classic yachts, coastal history, and private on-water celebrations, Sail Trim Again presents curated sail and charter options combining regional scenery with traditional maritime character.
Book with Sail Trim Again