Meet our Captains & Crew


Capt's Meredith & Jack

Captain Jack Spratt is Master & Captain of the historic yacht and finest wooden catboat ever built Trim Again, historic Sword fishing boat ENCORE . Jack holds a US Coast Guard Master of Steam, Motor & Auxiliary Sail, Near Coastal (200 miles off shore) 100 Ton license and an all oceans 200 ton international ticket. Jack is  a volunteer fire fighter and is the coxwin and marine assets trainer for the local fire and rescue squad. Jack is certified by U.S.C.G. in Search & Rescue operations. Jack has spent 40  years on the water including as rowing coach at the US Coast Guard Academy, New London. He has owned and maintained Trim Again for 33 years and restored and repurposed as a tour boat the sword boat Encore as a yacht 16 years ago. Jack has sailed the local waters for decades and knows all of the specialout of the mainstream places and many of the unique people that take a living FROM THESE SHORES. Captain Jack is an avid birder and holds a certificate from Cornell University Ornithology Lab with specific interest in migrating water birds. Jack has written and lectured on many topics of  local history and has in draft form the following books he plans to publish when he has to come ashore: From These Shores A Sea history of the Eastern waters of Long Island Sound, The Great Watch Hill Fire,  The Forgotten Gilded Age Hotels of Watch Hill & Fishers Island Sound and The History of The Watch Hill Life Saving Station. Jack is a frequent speaker at  Mystic Seaport Museum and in the summer weekly at The Ocean House. Captain Jack has written numerous articles about Watch Hill for various magazines. Jack and his boats have appeared in the movie, Hope Springs, on This Old House, Beach Front Bargin Hunt as well as in fashion magazines.   Jack has owned a cottage in Watch Hill for 30 years. A graduate of Cornell, Jack is Founder & Chairman of OHS Companies, A Healthcare Services Company in Old Lyme, CT.

Phone: 860 227-2339



Mike Fortunato,  Capt. Kristen Woodmansee, Capt. Jack Spratt

Kristen (Sept. 11, 1965 - Aug. 16, 2020) earned her Captains License while struggling with stage IV Cancer. Her kindness, positive attitude, passion for sailing and love of life lives on through these programs in her memory!

 K.R.I.S. Scholarships:

I. Mystic Seaport Museum's sail training schooner BRILLIANT.

II. NESS, New England Sailing & Science, Stonington


Kristen's Gift: A free weekly sunset sail for couples struggling with Cancer and partners in mourning.


Captain Meredith has sailed the seven seas aboard Tall Ships, traditional sailing vessels and yachts. She has raced in Classic Yacht Regattas all over the world. She has kayaked in the Artic, visited the remote Galapagos, Cook and Picairn Islands and dived for pearls in the Pacific. She is a much sought after rigger and delivery boat Captain. Meredith has worked on many ships of all sizes including; rigging and sail training crews of the 141 ft replica of the famous racing/fishing Schooner COLUMBIA the PRIDE of BALTIMORE, PICTON CASTLE, Schooner ADVENTURE, the luxury Dutch 250 ft. Clipper Ship STAD AMSTERDAM. Her lastest project was rigging and training the crew of the Chinese Navy's Sail Training Clipper Ship POLANG a 280 ft, 1,200 ton three masted square rigged. Meredith is a graduate of the University of Miami. Meredith holds a U.S.C.G. 250 Ton masters license and a 500 Ton mates license as well as having Dutch seamen papers

Capt. Meredith aboard the 141 ft. Schooner COLUMBIA during sea trials







Marty Hurley Paint & Varnish