Classic Sailing


The very best way to experience Watch Hill is from the water aboard the 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.

2Hrs $550


           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. $550

                             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. $550

                               1:00 p.m. - 3:00    ..... BOOK NOW


             Sea Breeze Sail: Not offered Sept 1- Oct.  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 sea breeze. 2 Hrs. $550

                                3:30 p.m.- 5;30    ..... 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.

Catering: Give us a call to order off our menu.

 Extra charge.

2Hrs $600  (includes Sparkling Wine)     

                                            Sunset Departure Times 

Departing Daily April  - November 15

   May - 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 - Sept 30:           5:00 p.m.

     Oct. 01- Oct. 22:            4:30 p.m.


Season Ends




              LEARN TO SAIL:

Whether you have never been on a sailboat, we offer private sailing lessons for any level of experience. 

Learn the principles of sailing, navigation, knot tying, cruising skills, boat handling, and any other sailing skill that you might need.

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, 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 $550

Half day, book Half day below

Call: 860.227.2339

 Champagne Brunch Sail:

Take a favorite Sunday activity out on the water and join us for a two hour, brunch of pasteries from the Sift Bake Shop, locally owned, French focused bakery specializing in artisanal breads, pastries and desserts, with sparkling wine or mimosas. We limit charter to six (6). This is a non-sailing charter aboard either ENCORE or TRIM AGAIN

2 Hrs $550
Departing: Sundays 09:00 a.m. July, Aug
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


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, the gentle night breeze carries our large sail along the calm waters of the bay. The wake shimmers in the moon light bioluminesence. light, 

2 Hrs: $ 600 

Call: 860.227.2339 



Trim Again has been in movies, fashion magazines and has witnessed numerous engagements, weddings, family gatherings, anniversaries and romantic dates. Couples, business groups, and bridesmaids have created life long memories 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, sunset cruises.


We do
Weddings - Engagements - Anniversaries - Birthdays