Adventure
Yachting & Sailing
Summer and Fall Off-site
Yachting
Dandy Two-Hour Luxury Yacht Charters
Built in France by Latitude 46–a company known for its classic design, high styling and impeccable construction, Dandy, an Andreyale 33, was inspired by the American commuter boats of the 1930s. The Dandy provides the ideal atmosphere for half- or full-day motored charters, cocktail or dinner cruises. Her roomy cockpit and vast salon with satin mahogany finish offer ample and elegant accommodations for up to six guests plus crew. Whether anchored in the Watch Hill Harbor of bay or cruising the open ocean, Dandy‘s shallow draft allows for exploration to remote and secluded destinations, making your cruise unique and unforgettable.
Includes: Boat excursion, non-alcoholic beverages, ice, snacks. The Sunset Cruise also includes sparkling wine and a cheese plate for you and your party.
Dandy At A Glance
- 33′ Latitude 46 Andreyale 33
- Motor yacht
- Accommodates up to six guests, per Coast Guard regulations; each guest must be a minimum of 4 years of age.
More About Dandy
Availability & Ages
- May 19 to July 31
- 12 noon, 3:00 p.m., 6:30 p.m. (Sunset Cruise)
- August 1 to August 25
- 12 noon, 3:00 p.m., 6:00 p.m. (Sunset Cruise)
- August 26 to October 8
- 11:00 a.m., 2:00 p.m., 5:00 p.m. (Sunset Cruise)
- All guests must be a minimum of 4 years of age. Dogs are not permitted in the boat.
Pricing
- Day Cruise (2 hrs): $500*
- Sunset Cruise (2 hrs): $650*
- 1/2 Day Cruise (4 hrs): $1,000*
- Full Day Cruise (6 hrs): $1,500*
- Each additional hour is based on availability at $250* per hour
* plus tax and 24% gratuity
Suggested Dress
Casual, non-slip shoes, and a warm jacket for evening cruises
Cancellation Policy
- 48-hour cancellation required to avoid cancellation fee.
- Cancellations within 48 hours of departure: 100% of cruise fee.
- Guests can reschedule their charter with 48-hour’s notice free of penalty.
- Cancellations due to weather (as determined by captain 30 minutes prior to departure) are fully refundable
Encore
Encore Historical Private Three State Tour
Experience Watch Hill, RI, Stonington and Noank, CT, and Fisher’s Island, NY from the water riding in style aboard the historic motor vessel ENCORE. This two-hour tour includes islands of the rich and famous, mansions, lighthouses, wildlife and the beauty of wild places and historic villages.
Time: 10:30 a.m. – 12:30 p.m.
Price: 2 Hrs. $500
Encore Historical Three State with Clam Shack Tour
Experience Watch Hill, RI, Stonington and, Noank, CT, Fishers Island, NY from the water riding in style aboard the historic 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. $600
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. $600
Encore Half Day Private Excursions:
Select from the following experiences: Mystic Seaport Museum & private tour, bird tour, Lighthouse tour, Montauk, historic Thames River, forts, U.S. Navy Sub Base, Coast Guard Academy. Captain Jack can customize to fit your interests. Price: $1,500
Encore Full Day Private Excursions to: Newport, The Hamptons, and Block Island.
Call Captain Jack to discuss the wide variety of custom excursions available from a day on Block Island, Newport, or The Hamptons. Price: $2,500
Images courtesy of the Westerly Sun
Sailing
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 Private 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. $500
Sail Trim Again Private 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. $500
Sail Trim Again Private 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. $500
Sail Trim Again Private 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. $600
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.
Additional Information About Sail Trim Again & Encore
Pricing & Times
- Encore Historical Private Three State Tour
- $500
- 10:30 a.m. to 12:30 p.m.
- Encore Historical Three State Tour with Lunch
- $600
- 10:30 a.m. to 1:30 p.m.
- Encore Afternoon Excursion
- $500
- 2 to 4 p.m.
- Encore Sunset Tour
- $600
- Two hour tour
- Encore Half Day Private Excursion
- $1,000, plus landing fees
- Encore Full Day Private Excursion
- $2,000, plus landing fee
- Encore Private Water Taxi to or from Ocean House
- $250/hour, minimum of one hour, plus landing fees and dockage
Cancellation Policy
- 48-hour cancellation required to avoid cancellation fee.
- Cancellations within 48 hours of departure: 100% of cruise fee.
- Guests can reschedule their charger with 48-hour’s notice free of penalty.
- Cancellations due to weather (as determined by captain 30 minutes prior to departure) are fully refundable
Adventure
Barton & Gray 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.
Additional Information
Cancellation Policy
- All cancellations within 7 days from the outing will be billed at 100%
- Cancellations 8 to 30 days before the outing will be billed at 50%
- Cancellations 30 or more days before the outing will be full refunded.
- Cancellations due to weather or maintenance will be fully refundable.