On the Water · Sag Harbor
Sailing Charter Sag Harbor
Sag Harbor Sailing has been putting people on 23-foot Pearson Ensigns since 1997, and they are real sailboats — no engine noise, no party barge, six people maximum. Take a licensed captain or take the tiller yourself; the day rate is the same either way. The boats live at the Yacht Hampton Boating Center on Pine Neck Avenue, a few minutes west of the village.
- Skill level
- All (captained)
- Season
- May-Oct
- Duration
- half day
- Cost
- Sailboat rentals from $475 plus fuel, staff and gratuity
- Group size
- 2-6
- Age
- All
- Gear
- Provided
- Weather
- 5-20 kt
Safety
Most trips stay inside the protected bays around Shelter Island and North Haven rather than heading offshore, which is what makes this workable for a first-timer. Weather cancellations earn a rain-date credit good for 28 months.
Where it happens
Operators (1)
Sag Harbor Sailing
Family-run and ASA-accredited, sailing out of Sag Harbor since 1997. The fleet is 23-foot Pearson Ensign keelboats seating up to six, rented with a licensed captain or bareboat at the same flat day rate, in 3-4 hour or 6-8 hour trips. Home base is the Yacht Hampton Boating Center at 51 Pine Neck Avenue — not Long Wharf — and there is no catboat in the fleet.
51 Pine Neck Avenue, Sag Harbor, NY 11963
Price: Day rentals of the 23-foot Pearson Ensign start at $475 plus fuel, staff and gratuity
Note: lat/lng is 51 Pine Neck Avenue, agreed to within 40 m by the US Census geocoder (40.99799, -72.34535) and Google Places (40.99788, -72.34576). The value held here until 2026-08-02 was 40.9988, -72.2923 — Long Wharf, 4.5 km east of the boats.