" She said yes!!!!!!!!!!!!!!!!!!!!!!! Jack thank you for making our engaement so special, from the Model T tour to the flowers, our personal play list and the perfect sunset. It was so special to sail back into the harbor in the dark with such beautiful music playing and the privacy you afforded us." Jenny & Ben Evenchik



Dear Capt. Jack,


Great sail and great conversation. Wonderful sailing lessons for our grandchildren. Many thanks for your unending efforts to preserve traditional seamanship values. Fair winds,

Roger F. Stone



It was fantastic!... 

However, the best part of our trip was chartering a sail boat on Saturday afternoon.  We chartered the boat 'Trim Again' for two hours.  We were picked up by Jack Spratt (owner of 'Trim Again' and our captain) in his very own Model T Ford.  When he heard that it was our first time in Watch Hill, he gave us a tour of the area on the model T before heading to the sail boat.  Upon entering the cabin of the sail boat there were a dozen roses and a personal note from Jack wishing us a happy anniversary.  He taught us all about sailing and let us drive the boat and get very involved while also giving us some alone time, encouraging us to sit at the front of the boat on our way back during the sunset.  I originally booked the boat for 2 hours, from 1:30pm - 3:30pm.  He asked if we had any other plans for the day which we did not and he gave us an extra 2 1/2 hours on Trim Again.  We didn't get back until after 6pm.  We toured the entire area, saw some beautiful homes on the water, it was a beautiful day and never got too chilly (he had blankets and coats on the boat if we did).  Jack even gave us some home made apple cider.  Susan, it was such a wonderful experience.  It reminded us of when we chartered a boat in st. tropez on our honeymoon.  Jack doesn't make anything off of these trips and he would not accept any tip from me after the trip.  If anyone of your clients like boating/sailing and you're sending them to ocean house, i would HIGHLY recommend booking a trip w/ Jack Spratt on his boat (Trim Again).



"Capt'n Jack, Thank you so much for two wonderful trips on the water and the sailing instruction! We have fallen in love with this place." Eileen & James Thomas


"What a fun time and the views are spectacular." Tom & Julie


"We loved our sail with you Jack! Thank you for the memory." Eileen & Brian Goldman


"Beautiful boat ENCORE, beautiful sunset. Wonderful food, Wonderful trip. Thank you." David Pakozdi



"A spectacular ride! We all had a lovely time...memories for ages." Devon



"Thank you for a beautiful evening- the perfect ending to an incredible holiday. The sunset was indescribaly amazing." Emma



"Jack, thank you so much for a truely stunning and informative evening tour. It was the highlight of our trip to the east coast and Ocean House." Brooke



"Jack provided one of the best boat rides I have had ever! A simply magnificant day in Watch Hill. ENCORE is simply beautiful to look at and to ride in thanks to Jack's efforts to maintain ENCORE so well." Wyatt


"Captain Jack, This investor conference was a huge success, in part because of you. It was truly an enjoyable experience working with you. Thank you especially for taking time out of your day to make a special trip to Shelter Island." Providence Investment Management.


Most amazing anniversary EVER! My husband gave me a most beautiful gift on a beautiful boat...life is the best." Jacqul & Fred




"Great experience relaxing trip."


"A real sea adventure with nostalgia and style! Captain Jack and his TRIM AGAIN is a beacon of light to the history of Watch Hill and a found treasure to all who want to experience  an authentic sea worthy path." Robert & Bonnie Vontell


"A very beautiful day with Capt. Jack, a marvelous boat and great company." Mary Beth Roncati Thierry Pruvot


"Teaching us how to sail the boat was was a great experience. I never thought that I was able to sail a boat. Capt. Jack made us feel comfortable. Interactive experience great conversation & teaching opportunity. Very personable & enjoyable. Great sea stories." Steve Robare


"Glorious sail, esquisite yacht, masterful captain. Great conversation and wonderful vistas." Bruce & Barbara Wiegand


"Definately the highlight of our trip to Watch Hill!!! Robin McKelle






"This (Capt Jack Charter) was the best part of our trip to Ocean House, Watch Hill" M&A


"Fabulous- just fabulous"


"Loved our experience on Trim Again but we enjoyed Capt. Jack more!" Fallon's Fleet


"Had a Great trip sailing on the Trim Again!!!! Angie and I enjoyed your boat as well as the time spent with you on Sat.!! We cannot begin to thank you for your thoughtfulness from the ride in the Model T to the roses and picture frame you gave us!! Again, a GREAT BIG THANKS!! "


"Thank you to Capt. Jack Spratt & Trim Again for an amazing sail to celebrate our 4th wedding anniversary. Jack, the flowers, hot apple cider and the unexpected ride on the Model T Ford made our day and we can't wait to return and have another sail on Trim Again! If anyone is visiting Ocean House ask for Jack Spratt and a sail on Trim Again!"


"Great time" DC


"Sincerest thanks for a fun and informative voyage on a beautiful fall morning on a beautiful boat." MB


"Fantastic time." JG


" Thanks for a great trip and entertaining all of Kadens questions. The Seals are a memory the kids will never forget. What a great day." K&NM


"This was awesome! The Seals were so cute! Thank you so much." Catlin


"Don't miss a tour with Capt. Jack Spratt, informative, spirited and fun! Thank you Jack." Shep


"Our family had a wonderful charter with Captain Jack. Our children loved the private tour of Mystic Seaport. The thoughtful gifts of compass and pirate hats for the boys was great. Highlight of our stay at the Ocean House" IK


"We had a great tour. No better way to spend a beautiful day" LN


"What a wonderful way to spend our 35th wedding anniversary. Love the personal tour. Thanks for the roses." J&S


"Thanks for a great learning experience with Capt. Jack on his beautiful boat." N&S


"Wonderful experience! Beautiful views, spectacular evening and so much knowledg. "


" Many thanks for the best birthday ever. Loved the special stop for fresh lobsters." L&R


"Capt. Jack, Thank you for a splendorous tour on our anniversary visit to the Ocean House. A true gift to meet you. What a glorious boat!" C&D


"Capt. Jack, We had an amazing time, breathtaking views a very knowledgeable interpreter" S&S


"Capt. Jack, Thank you for a wonderful experience. Spectacular evening and so much knowledge. Wonderful experience for a 6 year old and the highlight of Mothers Day weekend." K&E


"An absolute perfect day! Beautiful boat, wonderful captain/companion. Many thanks." PJ


"Dear Jack, You made our anniversary a most special day to remember always!" M&L


" An absolute highlight of our first ever family vacation. We've so grateful to our son's new pal, Capt. Jack for his hospitality, his warmth and one of the best experiences of our son's young life." S&H&L


"This was our son's first time on a boat! What a wonderful experience and what enjoyable company! Thanks Capt. Jack." J&E& G


" We want to thank you for making our anniversary so special. Each of the experiences you planned allowed us to appreciate the beauty of Mystic Seaport, the special visit to your friends on the island and the tour of the oyster farm, to the final music during the sunset. What a day!!!"