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Set sail on a private charter at sunset in stunning Westerly, Rhode Island. Enjoy sparkling wine, peaceful waters, and breathtaking views for a perfect romantic or family outing.
Set sail on a private charter at sunset in stunning Westerly, Rhode Island. Enjoy sparkling wine, peaceful waters, and breathtaking views for a perfect romantic or family outing.
Book with Sail Trim Again
Verified experiences and guided adventures in the surrounding area.
Operated by Sail Trim Again · Westerly, Rhode Island
Experience an unforgettable evening aboard the private sailing charter, Sail "TRIM AGAIN," on the serene waters of Fishers Island Sound in Westerly, Rhode Island. As the sun dips below the horizon, the sky transforms into a canvas of brilliant reds, oranges, and purples, providing the perfect backdrop for a romantic getaway or intimate family gathering. Whether you're celebrating a special occasion or simply seeking tranquility away from the hustle, this sailing adventure invites you to relax with a glass of sparkling wine while feeling the gentle breeze and the calm sway of the water. The expert crew ensures a smooth, safe, and personalized journey tailored to your desires, allowing you to soak in nature’s beauty in complete comfort and privacy. This sunset sail offers a rare chance to connect with loved ones, make new memories, and escape into the peaceful rhythm of the sea in one of New England’s most charming coastal spots.
easy.
2–3 hours.
Suitable for individuals with basic mobility; minimal physical exertion required.
Yes, children are welcome and can enjoy the calm and safe environment aboard the private charter.
Outside food and drinks are not permitted, but the charter provides sparkling wine and light refreshments.
In the event of unsafe weather conditions, the trip will be rescheduled or refunded.
The private charter comfortably fits up to six guests for an intimate experience.
No experience is necessary; the crew handles all sailing and navigation.
The departure point is at the Westerly Marina in Rhode Island, convenient for local and visiting guests.
Westerly was historically a key maritime hub, playing a significant role in New England’s coastal trade since the 18th century.
Local organizations actively work to protect the Fishers Island Sound ecosystem, promoting sustainable practices among charter operators.
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