Classic Sailing


The very best way to experience Watch Hill is from the water aboard the Historic wooden classic yacht TRIM AGAIN. We sail in the calm bay surrounded by wildlife preserves, nature, and beautiful unspoiled beaches. We head out into the sound and see lighthouses and historic villages. Learn about the history of the area. Take a turn at the helm. we limit guests to six for a truly intimate experience. All charters are PRIVATE. You are welcome to bring snacks and drinks, please no plastic coolers.

2 Hours: $500 High Season; June, July, August, Sept. 15

2 Hours $400 Off Season; April- May 15, Sept 16- Nov.1

2 Hour Sunset: $600 High Season;

2 Hour Sunset: $500 Off Season (April 20 - May 15) (Sept 15 -Nov 1)


           Morning Glory Sail: 

The morning is a special time on the water. This two-hour sail is in light breezes and calm waters. Great for those nervous about sailing or interested in learning to sail. 2 Hrs. $500

                             10:30 a.m.- 12:30    ..... BOOK NOW


            Afternoon Sailing Delight:

The mid-day sail is a perfect escape from the high noon summer sun and humidity. Always a breeze freshening as the afternoon winds shift around to the southwest. You can set your watch by the wind shift.

2 Hrs. $500

1:00 - 3:00

                                                  BOOK NOW


             Sea Breeze Sail: Not offered after Sept 1

The breeze freshens in the summer and great sailing is to be had. Enjoy the wind in your hair and the amazing feeling of a great wooden boat sail powered up by the sea breeze. 1.5 Hrs. $500

                                3:30 p.m.- 5:00    ..... BOOK NOW



            Romantic  Sunset Sail: 

This PRIVATE Charter includes sparkling wine. Departing Watch Hill. As the sun starts to set we head east so that you can watch the remarkable sky in this special place. Enjoy classical sunset romantic music while sipping on sparkling wine. Capt. Jack creates a private, just you and your party. As the sun sets we turn on our navigation lights and make our way into the harbor as the lights of the village reflect on the calm sea. Perfect for special occasions. We do engagements, weddings, anniversaries, and birthdays for groups of up to six.

 2Hrs $600  (includes Sparkling Wine) 

$500 Low Season Month: May, Sept 16, Oct & Nov 1


          Sunset Departure Times 

Departing Daily April  - November 15

                                                May 01 -  June 09         6:00 p.m.

  June 10- July 31           6:30 p.m.

  Aug 01 - Aug 31            6:00 p.m.

  Sept 01- Sept 15          5:30 p.m.

  Sept 16 - Sept 30         5:00 p.m.

  Oct. 01 - Oct. 20            4:30 p.m.


Season Ends



Full Moon Sail:

Once a month we head out as the sun is setting, the only sounds are the lapping of the bay on the wooden hull, and the gentle night breeze carries our large sail along the calm waters of the bay. The wake shimmers in the moonlight bioluminescence. light.

2 Hrs: $ 600 

 Full Moon Dates:

   May 21         Flower Moon

                             June 19      Strawberry Moon

                             July  19      Buck Moon (Friday)

                             Aug  17      Sturgeon Moon (Sat)

                             Sept 15      Harvest Moon (Sun)

                             Oct   15      Hunter's Moon


Call: 860.227.2339






Whether you have never been on a sailboat, are an experienced sailor, or would like to learn how to sail a gaff-rigged Catboat, we offer private hands-on, on-water sailing lessons aboard the historic Catboat TRIM AGAIN. This program is for individuals, families, or friends. The charter is private so only your group will be aboard.

Learn the principles of sailing, navigation, basic knots, and boat handling.


We offer a weeklong daily sail training program held in the morning, 3 hours from 10 to 1. The last day of the program is a half day, you and your team, or just yourself with the captain acting as your mate, will be responsible for planning, setting the sail, navigating, sailing her at all points of sail, emergency drills, dropping the sail and motoring into the harbor. If requested we could sail from Watch Hill, Fishers Island Sound, up the Mystic River into Mystic through two bridges, dock at Mystic Seaport Museum, and take a private tour of Mystic Seaport Museum with Captain Jack as your personal guide. This would be a full-day charter. Departing at 9 am and returning at 8 pm. 


Our Captains have many years of professional experience in private and group sailing instruction, as well as coastal and off-shore passage making.


For longer lessons, or special requests, book a custom package by calling.

If you imagine yourself at the helm of a classic sailing yacht, then call us for a TRIM AGAIN private lesson.

2 Hrs basics of sailing: $600

Weeklong Sail Training: $4000 plus the cost of admissions to Mystic Seaport Museum.


Call: 860.227.2339


Half Day Sailing:
Spend four hours sailing Fishers Island Sound and Block Island Sound in the luxury of this classic wooden yacht. Each half-day charter is customized to meet your interests including opportunities to stop off in Stonington.
Call 860.227.2339
Full Day Sail:
Spend the day sailing to Mystic Seaport Museum, or Fishers Island, or out to Block Island Sound. Each full-day charter is customized to your interests. 
Call: 860.227.2339





Trim Again has been in movies, and fashion magazines and has witnessed numerous engagements, weddings, family gatherings, anniversaries, and romantic dates. Couples, business groups, and bridesmaids have created lifelong memories of enjoying the natural beauty of the area aboard this incredible yacht.    

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 special places throughout the seashore. Step back in time to the peak of Watch Hill's Victorian Hotel and Cottage Colony 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 large 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 interior trim of teak and mahogany. 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 fixture in Watch Hill for over 30 years her Master and Captain, Jack Spratt offers a very special and unique experience. With her large cockpit, Trim Again is ideal for up to 6 guests for 2-hour, half and full-day sails, and sunset cruises.


We do
Weddings - Engagements - Anniversaries - Birthdays