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.
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Difficulty
easy
Duration
2–3 hours
Fitness Level
Suitable for most fitness levels; ability to move comfortably on deck is recommended
Wildlife
History
The Wooden Yacht TRIM AGAIN is a classic vessel, preserving traditional sailing craftsmanship dating back decades, tied to Rhode Island’s rich maritime heritage.
Conservation
Sail Trim Again supports local marine conservation efforts by promoting responsible boating practices and protecting coastal ecosystems.
Sail Trim Again
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.
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 Orientation
Plan to arrive at least 15 minutes early to get briefed on safety and sailing basics before departure.
Wear Layers for Changing Weather
Ocean breezes can fluctuate, so dressing in layers keeps you comfortable throughout your sail.
Bring Seasickness Remedies
If you're prone to motion sickness, take preventative measures to ensure a smooth journey.
Use Reef-Safe Sunscreen
Protect your skin while respecting marine life by applying reef-safe sunscreen before boarding.
Windbreaker Jacket
Protects against unpredictable spring breezes and light rain.
spring
Sunglasses
Shields eyes from the bright sun reflecting off the water.
summer
Non-Slip Deck Shoes
Provides stability and safety while moving around on the yacht’s wooden deck.
Warm Layered Clothing
Keeps you comfortable amidst cooling fall temperatures on open water.
fall