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.
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Difficulty
easy
Duration
3 hours
Fitness Level
Suitable for most fitness levels as the tour is seated and relaxed with minimal physical exertion.
Wildlife
History
The Tri-State coastline played a critical role in maritime trade and lighthouse development dating back to the 18th century.
Conservation
Efforts are ongoing to protect the rich coastal ecosystems here by promoting responsible boating and habitat preservation.
Sail Trim Again
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.
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.
Location
Westerly, RI
Departures around Watch Hill
Classic Yachts
TRIM AGAIN & ENCORE
Wooden yacht and historic motor yacht
Trip Lengths
Morning–3 hrs
Options from short sails to 3-hour tours
Private Charters
Available
Ideal for celebrations and romance
Reserve a morning sail, sunset cruise, or multi-hour historical tour aboard TRIM AGAIN or ENCORE — private bookings available for celebrations and sightseeing.
Bring a light jacket
Coastal breezes can be cool even in summer, so layering helps keep comfortable.
Wear non-slip shoes
Boat decks can be slippery, so sturdy footwear improves safety while aboard.
Arrive early for parking
Parking near Westerly harbor fills quickly, so plan extra time before departure.
Bring a camera with zoom
Wildlife and scenic mansions are best captured with a lens that can zoom in.
Sunglasses
Protect your eyes from glare reflecting off the water during sunny days.
summer
Light waterproof jacket
Keep dry and warm during occasional coastal showers or breezes.
spring
Binoculars
Enhance wildlife watching and scenic views from the boat.
Comfortable non-slip shoes
Ensure safety and comfort while moving on wet or uneven boat surfaces.