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.
More ways to explore the area's outdoor wonders
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Difficulty
easy
Duration
2 hours
Fitness Level
Suitable for all fitness levels, no strenuous activity required – mostly sitting and light mobility onboard.
Wildlife
History
Fishers Island Sound has long been a vital waterway for both Native American tribes and early European settlers, with historic maritime routes dating back centuries.
Conservation
Sail Trim Again practices low-impact sailing methods to protect the local marine ecosystem, promoting conservation of Fishers Island Sound's natural environment.
Sail Trim Again
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.
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.
Arrive Early to Embark Smoothly
Plan to arrive at least 15 minutes before your scheduled departure to allow time for check-in and a smooth boarding process.
Dress in Layers
Coastal temperatures can drop quickly after sunset, so bring a light jacket or sweater for comfort during the evening sail.
Bring a Camera or Smartphone
Capture the spectacular sunset hues over Fishers Island Sound, but secure your device to avoid dropping it overboard.
Be Mindful of Seasickness
If you're prone to seasickness, consider taking preventive medication before the cruise or consult the crew for tips.
Light Jacket or Sweater
Keeps you warm as the temperature drops after sunset.
fall
Sunglasses
Protect your eyes during the daylight portion of the cruise.
summer
Camera or Smartphone
Capture the vibrant colors of the sunset and special moments.
Non-slip Shoes
Ensure safety while moving around on deck.