30’ sloop sail boat.
,
30 ft
Boat length
Up to 6
Passengers
Captained
This boat is rented with a captain
86%
Owner’s response rate
The boat
⛵ Classic Pearson 303 Sailing Charter – Captain Included
Step aboard a beautifully maintained 1986 Pearson 303, a classic cruising sailboat known for its comfort, solid build, and smooth performance on the water. Based on the scenic waters of Long Island Sound, this 30-foot sloop is the perfect way to enjoy a half-day, full-day, or sunset sailing adventure—with a licensed and experienced captain at the helm.
⚓ Features:
30' LOA (Length Overall) – spacious cockpit and cabin
Yanmar inboard diesel engine – reliable auxiliary power
Comfortable for up to 4–5 guests for day sails
Shaded cockpit with Bimini cover
Well-equipped galley and enclosed head (toilet)
Bluetooth speaker system for music
Cushioned seating topside and below
🧭 What to Expect:
Whether you want a relaxing sail, a hands-on sailing lesson, or a private celebration on the water, I’ll tailor the experience to you. We’ll explore scenic coves, spot local wildlife, and enjoy the calm and beauty of Long Island Sound. Bring your own food and beverages, or I can help arrange catering.
🧑✈️ About the Captain:
I’m your onboard captain and host. I know this boat intimately and the surrounding waters even better. Safety, fun, and a smooth sailing experience are my top priorities. You can sit back and relax—or help trim the sails and learn something new!
📍 Departure:
Flexible pickup points around Setauket, Port Jefferson, and nearby harbors
Custom itineraries available
Read more
Owned by
Barry
Amenities
Bathroom
Stereo
Stereo Aux Input
Cooler / Ice chest
Swim ladder
Shower
Anchor
Grill
Depth finder
GPS
VHF Radio
Specifications
Year
1986
Length
30 ft.
Make
Pearson Yachts
Model
303
Capacity
6
See all
/ (excl. fees)
You won't be charged yet
Ratings & reviews
Boat location
Exact location information is provided after a booking is confirmed.
Your crew
Boat owner
Barry
Earned my first boating license at age 13. Sailed a Pearson ensign 22 for several years I owned a Tartan 27 for a few years and a Catalina 22 for about 12 years. My current boat is a Pearson 303. I received my US Coast Guard OUPV captains license this past March.
When you rent the Pearson 303, you will also have me as your captain, so no sailing experience is needed. You can help out if you wish or just relax and enjoy the sail.
Wear appropriate boat shoes or white bottom sneakers. Barefoot is always fine. Any questions, just ask.
See profile- Response rate: 86%
- Avg. response time: < 48 hours
Things to know
Allowed on boat
swimming
alcohol
kids under 12
glass bottles
red wine
Cancellation policy flexible
- Free cancellations until 24 hours before the booking start time.
- Cancellations within 24 hours of the booking start time are non-refundable.
Security deposit
A security deposit hold (not a charge) will be placed on your credit card 48 hours before your booking starts to cover any incidental damage that may occur during your rental. This hold is released 48 hours after the booking is complete, if no claims are made. The security deposit amount for the boat you are booking will be outlined during the check-out process.
Learn more