Our two classic yachts, Dolphin and Nautilus, were racing vessels in their heyday.  One look at them evokes the beauty of sailing. At Oakcliff they are sailed and raced nearly every day. Throughout the spring and fall they fill Oyster Bay with their graceful presence. On weekends, along with other classics in Oyster Bay, they head out on a pursuit race at midday, and on Thursday evenings the classics sail the same course while the setting sun glistens on time-worn but exquisitely restored wood.

Dolphin is a Herreshoff design, a Newport 29. She was launched in 1914 and is 35’7” overall and 29’ on the waterline. She raced successfully for many years, including three years in the Mediterranean, sailing in the classics regattas of Mallorca, Menorca, Imperia, Cannes and St. Tropez.

Nautilus, the oldest classic in the fleet, was built in Bristol, Rhode Island in 1905, also by the Herreshoff Manufacturing Company. She is a NY30 design, gaff-rigged, with an overall length of 43’ and a waterline of 30’.

As a special privilege, Oakcliff Supporters are invited to take advantage of the Vintage Yacht Club at a discounted rate. Through this arrangement you can sail aboard one of our yachts or choose from their extensive fleet. Download the details here.