Experience the natural beauty of our coastline aboard our classic motor and sailing yachts. From late May to early October, Ocean House offers four extraordinary and very different boats for your New England yacht chartering experience. Located a mere three-minute walk down the hill from Ocean House, the fleet offers many ways to enjoy the water.



An Andreyale 33, Dandy was built in France by Latitude 46, a company known for classic design, high styling and impeccable construction. Its design was inspired by the American commuter boats of the 1930s. As the primary member of the Ocean House fleet, Dandy provides the ideal atmosphere for half- or full-day charters, cocktail or dinner cruises. Her roomy cockpit and vast salon with satin mahogany finish offer ample and elegant accommodations for 4–6 guests plus crew. Whether anchored in the harbor or bay or cruising in open waters, Dandy has a shallow draft that allows for exploration of remote and secluded destinations, making your luxury yachting charter unique and unforgettable.

Trim Again


Sailing with Captain Jack aboard Trim Again is a Watch Hill must-experience. Trim Again brings you back to the Golden Age of Watch Hill’s famous fashionable seaside hotels and the romance of yachting excursions in the 19th century! Trim Again has been the subject of many articles and has appeared in movies and fashion magazines. Her log is replete with engagements, anniversaries, birthdays and wonderful quotes from her many famous guests and memorable passages. Sailing aboard Trim Again, a classic wooden yacht designed for comfort and elegance, is a delight to the senses. Relax to the sound of the calm sea lapping against Trim Again’s cedar hull. Enjoy the cool summer shade provided by an enormous sail, delight in a stunning sunset as the last rays of daylight dance on the gentle ripples of her wake. Marvel as flocks of birds (least sandpipers, snowy egrets) alight on the marsh surface, glimpse an osprey or tern fishing on the bay as you sail along the beautiful landscape of the perfect isolated beaches and forests of our bay and sound. Varnished to perfection and roomy enough for six guests, her large cockpit is ideal for romantic sunset cruises, engagements, anniversaries, family gatherings, company retreats, bird watching, photography and more. Captain Jack encourages all guests to take the helm and sail the boat.

Interested in a sailing lesson? Captain Jack offers private sailing instruction aboard Trim Again and his classic 1923 Herreshoff Watch Hill 15 racing sloop, Pixie.

  • Ninety (90) minute daily charters (3 pm departure),
  • Two, Three, Half and Full day excursions available by appointment (see www.sail-trim-again.com).

Captain Jack donates his charter fee to support the Mystic Seaport Museum and New England Science & Sailing Foundation, NESS, Stonington, CT.

Captain Jack’s Historical Watch Hill Land & Sea Tour

A private 90-minute land & sea tour of Watch Hill begins with a ride in Captain Jack’s 1913 Model T Woodie Wagon; next, climb aboard Encore or Trim Again for a tour of Watch Hill from the sea.

Departs at 9:00 a.m. in July & August. Other dates and times are available. Pick-up & drop-off is at the entrance of Ocean House.

Fee: $250 for up to four guests. Children of all ages or welcome.

Captain Jack’s Encore Lobster Shack Lunch & Historical Three-State Lighthouses Cottages & Nature Tour


Encore is a beautiful classic wooden yacht offering daily historical three-state three hour tours with a stopover for lunch at a shorefront lobster shack (price of lunch not included). Encore was a swordfish/tuna fishing charter boat out of Montauk, N.Y. and for fifty (50) years hosted many famous people including Richard Burton and Elizabeth Taylor and appeared in movies, television shows and fashion magazines. Captain Jack restored and repurposed Encore to be a luxurious Watch Hill tour boat. Well-known for her historical three-state, lighthouse, harbor seals, sunset excursions and behind-the-scenes guided tours of Mystic Seaport Museum. Fast (700 HP), stable and comfortable with a spacious cockpit for up to six guests. Also available for half and full-day excursions by reservation (www.sail-trim-again.com) through October 15, 2018.

Historical Three-State Tour
Saturday – Wednesday from 11:00 a.m. to 2:00 p.m.
June 2 – September 5, 2018
Other days & times available upon request.

Encore Water Taxi Service to Fishers Island Golf Club (East Harbor), Fishers Island Wester Harbor, Block Island, Montauk, Greenport, Shelter Island, Newport, New London.

Hinckley Picnic Boat EP


Ocean House has partnered with Barton & Gray, one of the most unique clubs in North America, to provide guests and members with an exclusive opportunity to reserve a luxury yachting charter this summer. Cruise to Newport and Montauk, Mystic or Fishers Island aboard a 36-foot Hinckley Picnic Boat EP, captained and cared for by a United States Coast Guard licensed crew. Available daily for half-day morning or afternoon New England yacht charters, are suitable for up to six guests. With a single jet-drive propulsion system, shallow draft, and easy stern access, the Picnic Boat is the perfect yacht for ocean adventure or shallow cruising.

Explore Ocean Escapes Brochure

Charters and Tours

Public and private charters are available, as well as cocktail and dinner cruises in the evenings with catering provided by Ocean House. Explore what the fleet offers:

Dandy Day & Sunset Charters
Sailing Day & Sunset Charters
Area Yacht Tours

Boats at a Glance


• 33' Latitude 46 Andreyale 33
• Motor yacht
• Accommodates up to six adults

Trim Again

• Classic wooden sailing yacht (historic catboat)
• Sail boat
• Accommodates up to six guests


• Mackenzie Cuttyhunk wooden repurposed swordfishing vessel
• Classic wooden motor yacht (700 HP)
• Accommodates up to six guests, children of all ages welcome

Hinckley Picnic Boat EP

• 36' Hinckley
• Motor yacht
• Accommodates up to six adults

Cancellation Policy

• 48-hour cancellation required to avoid cancellation fee.
• Cancellations within 24 to 48 hours of departure: 50% of cruise fee.
• Cancellations within 24 hours of departure: 100% of cruise fee.
• Cancellation fees can be credited towards a future booking.
• Cancellations due to weather (as determined by captain 30 minutes prior to departure) are fully refundable.