Private sails and scenic charters from Westerly, Rhode Island aboard the wooden yacht TRIM AGAIN and historic motor yacht ENCORE.
Choose morning, afternoon, sunset or multi-hour sightseeing tours around Watch Hill, Stonington and Fishers Island.
boat-charters · Westerly
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.
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.
“Every outing is organized with local river knowledge, basic safety instruction, and equipment checks before departure.”
Departures around Watch Hill
Wooden yacht and historic motor yacht
Options from short sails to 3-hour tours
Ideal for celebrations and romance
Open the individual experience guide to confirm current availability, pricing, policies, conditions, and inclusions before booking.
The operator provides clear meeting points, departure times, and destination coordinates for all outings.
Personal flotation devices, emergency protocols, equipment checks, and paddling orientations are provided before departure.
Recommended layering, water shoes, sunscreen, and dry bags are detailed in each experience guide.
Guides share rich knowledge of regional flora, fauna, scenic landmarks, and river navigation.
A glimpse into the experiences, natural landscapes, and adventures waiting on your next trip.
Images supplied on the current Sail Trim Again listing.
Sail Trim Again offers a variety of guided outdoor excursions, scenic routes, rentals, and custom itineraries tailored for families, couples, and adventure enthusiasts.
Yes. Most trips feature comprehensive safety orientations, equipment fittings, and calm routes suited for first-time adventurers. Check the details on individual experience guides for specific age and skill requirements.
Standard safety equipment (such as certified life vests and essential gear) is supplied for each booking. Detailed checklists regarding weather-appropriate attire and personal items are provided prior to departure.
Reserve a morning sail, sunset cruise, or multi-hour historical tour aboard TRIM AGAIN or ENCORE — private bookings available for celebrations and sightseeing.
boat-charters · Westerly
Enjoy a private two-hour sunset cruise on Fishers Island Sound near Westerly, Rhode Island. Celebrate with sparkling wine and stunning views on this unforgettable sailing experience.
boat-charters · Westerly
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.
water-activities · Westerly
Explore the coastlines of Rhode Island, Connecticut, and New York aboard the historic yacht ENCORE. Discover lighthouses, wildlife, and local history on this exclusive two-hour boat tour.
boat-charters · Westerly
Set sail on the ENCORE for a scenic 3-hour tour along Rhode Island’s coast with a tasty lobster and clam lunch at the seaside. Explore historic shores and enjoy wildlife spotting on this unique Tri-State adventure.
Click into any experience card above to view current dates, live availability, transparent pricing, cancellation policies, and booking details.