experiences

Yachting

Yachting

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.

Dandy

dandy

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.

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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.

Sail Trim Again Morning Glory
Sail aboard the classic Wooden Yacht TRIM AGAIN in the calm waters of the bay, the Harbors of Stonington and Watch Hill and on Fishers Island Sounds.  Enjoy the beauty of Watch Hill, Stonington, Fishers Island Sound from the sea. 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.
Time: 10:30 a.m. – 12:30 p.m.
Price: 2 Hrs. $400

Sail Trim Again Afternoon Sailing
Afternoon Sailing Delight: 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 (6) for a truly intimate experience. All charters are PRIVATE. You are welcome to bring snacks and drinks, please no plastic coolers. The mid-day sail aboard the wooden sailing yacht TRIM AGAIN 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.
Time: 1:00 p.m. – 3:00 p.m.
Price: 2 Hrs. $400

Sail Trim Again Sea Breeze Sail
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 (6) for a truly intimate experience. All charters are PRIVATE. You are welcome to bring snacks and drinks, please no plastic coolers.
Time: 3:30 p.m. – 5:30 p.m.
Price: 2 Hrs. $400

Sail Trim Again Sunset
Come aboard and experience some of the most amazing sunsets on Fishers Island Sound and in the Bay. Includes 1 bottle of sparkling wine. Perfect for engagement, anniversary, romantic date, family gathering, wedding vows. Sailing with only the sound of the water against the wooden hull and the wind in the gaff rigged sail.
Price: 2 Hrs. $500

encore

Encore Historical Three State Tour
Experience Watch Hill, RI, Stonington, Noank and Groton, CT from the water riding in style aboard the motor vessel ENCORE. This two hour tour includes mansions, lighthouses, wildlife and the beauty of wild places and historic villages. Includes stop for lunch at a local seaside Lobster & Clam Shack.
Time: 10:30 a.m. – 12:30 p.m.
Price: 2 Hrs. $400

Encore Historical Three State with Clam Shack Tour
Experience Watch Hill, RI, Stonington, Noank and Groton, and CT, Fishers Island, NY from the water riding in style aboard the motor vessel ENCORE. This three-hour tour includes mansions, lighthouses, wildlife and the beauty of wild places and historic villages. Includes stop for lunch at a local seaside Lobster – Clam Shack, cost of lunch NOT included in charter fee.
Time: 10:30 a.m. – 1:30 p.m.
Price: 3 Hrs. $500

Encore Sunset Tour
Amazing sunsets on Fishers Island Sound and in the Bay. Includes 1 bottle of sparkling wine. Perfect for engagement, anniversary, romantic date, family gathering, wedding vows.
Price: 2 Hrs. $500

Pixie 1923 Herrshoff Racing Sloop
We limit PIXIE to two (2) guests. We sail off and on her mooring in Watch Hill Harbor. Your party goes to the Watch Hill Yacht Club. Park in the lots on Bay St. go to the Yacht Club and take the launch out to PIXIE, your Capt. will be waiting for you.

Captain Jack donates his charter fee to provide scholarships to Mystic Seaport Museum’s Sail training program BRILLIANT and to the STEM educational program NESS, New England Sailing and Science program in Stonington.

Please note: Captain Jack will sail in most weather such as showers, but not in fog, thunderstorms, or high wind warnings. The Captain may cancel the charter or return to the dock at any time based on weather conditions.

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Hinckley Picnic Boat EP

encore

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

Dandy

• 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

Encore

• 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.

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