Sail TRIM AGAIN
Sail Watch Hill & Stonington in Timeless Comfort
The Best Way to Experience Watch Hill
Whether celebrating a special occasion, planning a romantic evening, entertaining guests, or simply relaxing on the water, a private sail aboard TRIM AGAIN offers a timeless New England coastal experience you’ll never forget.
Private Charters Aboard the Historic Yacht TRIM AGAIN
Experience the beauty of coastal Rhode Island and Connecticut the way it was meant to be seen — from the water.
Join local Captain, life long waterman, and historian Capt. Jack Spratt aboard TRIM AGAIN, a beautifully maintained historic wooden sailing catboat yacht, for an unforgettable private sailing experience departing from picturesque Watch Hill. Sail through the calm waters of Watch Hill Harbor, into the scenic bay and Pawcatuck River, and out across Fishers Island Sound, surrounded by wildlife preserves, historic shoreline, and beautiful unspoiled beaches. Just a walk down the hill from the OCEAN HOUSE.
TRIM AGAIN’s wide beam provides exceptional stability, allowing her to sail comfortably without excessive heeling — creating a smooth, relaxing experience ideal for guests of all ages. Capt. Jack calls it the Zen of sailing. Feel the fresh sea breeze, listen to the gentle sound of water lapping along the hull, and relax beneath the shade of her magnificent sail as you take in the coastline from a truly unique perspective.
A Truly Private & Intimate Experience
Every charter is completely private, with Capt. Jack welcoming a maximum of just six guests aboard — ensuring personal attention, comfort, and an unforgettable shared experience with family, friends, or someone special.
Guests are invited to:
Take a turn at the helm and learn traditional sailing
Discover local maritime history
View nearby lighthouse and historic coastal villages
Enjoy peaceful wildlife and protected shoreline scenery
Children of all ages are welcome, making this a perfect outing for families, couples, and small groups alike.
Charter Options
Choose the perfect time to sail:
☀️ Morning Glory — 10:00 AM- 11:30
🌊 Afternoon Delight — 1:00 PM- 2:30
⛵ Sea Breeze — 3:00 PM - 4:30
🌅 Romantic Champagne Sunset Experience
Sunset sails offer especially magical views as golden light settles over Watch Hill and Fishers Island Sound, (includes a bottle of sparkling wine).
Step aboard. Take the helm. Let the wind carry you.
👉 Reserve Your Private Charter Today
Daily Charters May - October
Trim Again Adventures
Departing 10:00, 1 & 3:00
$500
Captain Jack Spratt, local historian offers his historic classic wooden Catboat Sailing Yacht, TRIM AGAIN, for private (just you & your guests), (1.5) hour morning, afternoon, and evening as well as sunset sails. Half-day excursions and custom charters are also available. We take up to six guests to create an intimate experience. Everyone is encouraged to sail the boat.
Sightseeing while learning about the Mansions, Lighthouses, Fort, People, and History of Watch Hill, R.I., Fishers Island, N.Y., and Historic Stonington, CT.
Experience the natural beauty of the barrier beaches, marshland, Bay, and sound.
Observe the migratory shore birds, Ospreys, Eagles, Oyster farms, Fishing, and scallop boats.
Learn how the great Hurricane of 1938 changed the landscape.
Interested in a family gathering? Sailing aboard a historic classic wooden Catboat yacht, listening to the sounds of the water lapping on the hull, the sound of the wooden spars taking up and the feeling of being close to the water but never heeling over (Catboats are very stable and do not lean over, tiliting like modern sailboats) is the perfect venue for a romantic date, anniversary, engagement, intimate wedding, or a sunset sail with sparkling wine!
Interested in learning to sail a classic gaff rigged yacht or honing your sailing skills? Capt. Jack makes it fun, informative, and relaxed
Sunset Sail
$600
Sunset charters are the most romantic!
The sunsets are stunning out on the clam bay off Watch Hill.
We like to stay out past sunset to see the sky change colors. As we drop sail, or motor home the sounds of cannons from the areas yacht clubs can be heard along with the horns, whistles on anchored boats in the bay. Watch as the birds fly to their roosts and listen to the bell buoy and foghorn in the background as the wake grows ever darker as we dock.
1.5 Hrs. $600 (includes Sparkling Wine).
Sunset Departure Times
May 01 - June 10: 6:00 p.m.
June 11 - July 31: 6:30 p.m.
Aug 01 - Aug 31: 6:00 p.m.
Sept 01 - Sept 13: 5:30 p.m.
Sept 14 - Oct. 01: 5:00 p.m
Oct. 02 - Oct. 22, 4:30 p.m.
3 Hours
Call to book 860.227.2339
$1000
Call to discuss options for 3 hour or full day excursions. 860.227.2339 Here are a few examples
Having a local Captain will make your experience exceptional. With over 30 years of local knowledge, our Captains know the best places and are welcomed in all ports of call. Full Day Charters are available on weekdays from June to July and until August 15.
(Limit 6 Passengers)
Sail the Calm Waters of the Sound, Bay and River
Amazing Sunset Experiences
Catboat Yacht TRIM AGAIN
Legacy of the historic elegance of Watch Hill at the height of the Victorian Fashionable Hotels
Trim Again is the perfect sensual yachting experience. From her exquisite varnish finishes, brilliant shining nickel-plated hardware, and large wooden spars to her massive sail, this wooden boat sails, smells and sounds like nothing you have ever experienced. Her majestic Sail shades the cockpit and her kind sailing characteristics (she does not heel over) and shallow draft provide access to remote and unique places throughout the seashore.
Step back in time to the peak of Watch Hill's Gilded Age era of Catboat party boat tours sailing on the Bay, Fishers Island Sound, River and Ocean.
A founding member of the Catboat Association, Trim Again has been described as the ultimate Catboat Cruising Yacht. At 24' by 11'3" she is a significant and original wooden Catboat. Built for a wealthy coffee merchant (Victor Coffee), no expense was spared in her construction, materials, and maintenance. Her galley is stainless steel (a gift from Howard Johnson). Trim Again's decks are of teak, her cockpit and house combings of steam bent oak, and her cabin sole finished in teak with mahogany interior. She is finished to perfection, varnished inside and out. In 2009 her bottom was refastened with 1,350 Monel fasteners (screws) at a cost of $4.10/ screw to ensure her life span would exceed 100 years!
A historic fixture in Watch Hill, her Master and Captain, Jack Spratt, donates a portion of charter fees to support the Mystic Seaport Museum's Schooner BRILLIANT Youth Sail Training Program and Scholarships for week-long STEM immersion on water programs of New England Science & Sailing.
With her large cockpit, Trim Again is ideal for up to 6 guests for 1.5- or 3-hour, full-day sails, sunset cocktails, and light dinner fare cruises.
Sunset - Moonlight - light Dinner- Wine Tasting - Harbor Tours- Excursion to Fishers Island
Learn to Sail- Nature - Engagement- Anniversary- Birthday
History of Catboat TRIM AGAIN
TRIM AGAIN is the last Watch Hill wooden catboat in the tradition of the Gilded Age, offering hotel guests and day-trippers sailing excursions in the age of sail. Catboats lined both sides of Watch Hill and Plimpton Docks during the peak years of the Ocean House, Larkin House, Plimpton House, Watch Hill House, and Narragansett House from 1870 - 1929.
Captains would leave their sails up to dry in the morning breeze and wait for hotel guests to arrive aboard these "party boats" for a day. Women would be in dresses and men in jackets and ties. They would sail the bay and up along the Pawcatuck River. As they did not have power, they often arrived late back to the dock. Dodging Steamships was something of a sport that came to Watch Hill from Stonington and Westerly, often resulting in harsh words exchanged between Steamboat and Catboat Captains, and at times fights at the dock.
