We cater to those who are adventurous, active, want to improve their sailing skills or perhaps just enjoy the experience of sailing in pristine Greenport Harbor.
Our nimble and responsive 33-foot J Boat is built for racing, with a surprisingly spacious and comfortable cockpit. Or we can sail your boat.
It's All Connected
All charters are 3-hour minimum, maximum 6 guests; options listed here may overlap or need to be modified depending on time, tide and wind. Custom charters are also available. Please ask what interests you.
Tide and wind will determine our route as we make our way past Long Beach Bar Lighthouse and out into Gardiner’s Bay, a relaxing reach along the eastern shore of Shelter Island toward Cedar Beach Lighthouse at the entrance to Northwest Harbor. There is also an opportunity to drop anchor along Long Beach Bar and plunge into the cool, clean water.
Local Color, Fascinating History
Greenport and nearby harbors are home to some very fine yachts. Sailing through them in all their diversity can be thrilling and inspiring. This deep and protected area has a long and varied history – there is evidence on every shore of the interplay of man and nature. From whaling days to the present, there have been many chapters in our local history.
Through the Headlands
Heading west through Greenport Harbor we enter into the Peconic estuary and choose a course navigating the local currents in Pipes Cove, Southold Bay, Shelter Island Sound and Noyack Bay. A more challenging sail.
This is for the racing enthusiast, whether beginner or more advanced. Choosing a course and challenging the tides and wind can make for an exciting adventure in our fast and responsive boat.
We also offer sailing advice
We have the experience to sail just about any boat and can help you make yours sail faster. We can advise you how to tune your rig, adjust your sails and play the currents for maximum boat performance. Please contact us.
What we provide:
Ice and drinking water
A cooler for your provisions
What to bring:
A Sense of adventure
Sneakers or boat shoes
Windbreaker in spring and fall
Sun protection, long sleeved shirt
Snacks and beverages
Cash to tip crew
What not to Bring:
Business worries, fear
We want to assure you that every precaution has been taken to ensure a safe trip.
All crew members have been vaccinated.
Masks will be worn when in close contact.
All surfaces with be thoroughly cleaned before your charter. Hand sanitizer will be available.
We try to only do one charter a day, allowing time to properly sanitize working surfaces.
If high winds or steady rain prevent the boat from sailing, an alternate date will be offered.
Marine forecasts are monitored and a decision will be made 2 hours before departure.
A full refund will be given 7 days
before scheduled sail.
50% Refund is offered 2-6 days before sail.
No refund is offered 48 hours
before scheduled sail.