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.
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Difficulty
easy
Duration
2–3 hours
Fitness Level
Suitable for individuals with basic mobility; minimal physical exertion required.
Wildlife
History
Westerly was historically a key maritime hub, playing a significant role in New England’s coastal trade since the 18th century.
Conservation
Local organizations actively work to protect the Fishers Island Sound ecosystem, promoting sustainable practices among charter operators.
Sail Trim Again
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.
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 for Best Boarding Experience
Plan to arrive at least 15 minutes early to check in and get settled before departure.
Wear Non-Slip Shoes
Choose footwear with good grip to navigate safely on the boat's deck.
Bring a Light Jacket
Evenings on the water can get cool, so a light windbreaker or sweater is recommended.
Limit Alcohol Consumption
Enjoy the included sparkling wine responsibly to stay alert and safe during the sail.
Non-slip Boat Shoes
Help maintain stable footing on the deck in all weather conditions.
Light Jacket or Windbreaker
Useful to stay warm during cooler spring evenings on the water.
spring
Sunglasses
Protect your eyes from sun glare reflecting off the water during summer sunsets.
summer
Camera or Smartphone
Capture stunning sunset moments and beautiful coastal scenery.