Jack's vision for Sail TRIM AGAIN & ENCORE Historical Tours 16 years ago was  to share the beauty, history, and wildlife of the ocean, bay and river that surround Watch Hill aboard his classic wooden yachts. Captain Jack Spratt is the Master & Captain of the historic yacht, and the finest wooden catboat ever built Trim Again, and the historic Sword fishing boat ENCORE. Jack holds a US Coast Guard Master of Steam, Motor & Auxiliary Sail, Near Coastal (200 miles offshore) 100-Ton license, and a 200-ton international ticket. Jack is a semi-retired healthcare entrepreneur, a retired volunteer Watch Hill firefighter, and has a U.S. Coast Guard Joint Search & Rescue (JSAR) operations certification. Jack is also the novice rowing coach at the U.S. Coast Guard Academy (1976, 1989, and 2024-).  Jack has spent 40  years on local waters.  He has owned and maintained Trim Again for 35 years. Jack restored and repurposed, as a tour boat the sword-boat Encore as a yacht 20 years ago. Jack has sailed the local waters for decades and knows all of the special out-of-the-mainstream places and many of the unique people that take a living FROM THESE SHORES. Jack is the author of: Watch Hill, 1886, Windmills of Watch Hill, Watch Hill Life Saving Station, The Great 1916 Watch Hill Fire, Napatree & Sandy Point, A History of Fort Mansfield.

Jack offers scholarships for teens to Mystic Seaport Museum's sail training program aboard the schooner BRILLIANT and through scholarships to attend New England Science & Sailing programs in Stonington Ct. 

Phone: 860 227-2339