On the Water · Sag Harbor
Sailing Charter Sag Harbor
Long Wharf in Sag Harbor is the East End's busiest charter dock — four operators run sail trips out of the same village pier, from a $95 catamaran sunset to a six-figure private yacht week.
- Skill level
- All (captained)
- Season
- May-Oct
- Duration
- half day
- Cost
- $150-300/person
- Group size
- 2-6
- Age
- All
- Gear
- Provided
- Weather
- 5-20 kt
Safety
Long Wharf is dog-friendly but afternoon SW chop builds fast inside the bay — kids prone to seasickness do better on a morning charter.
Where it happens
Operators (4)
Sailaway Sag Harbor
Captained day, sunset, and harbor tours from Long Wharf
Long Wharf, Sag Harbor, NY 11963
Price: $200/person, 2-hour charter
Diamondtail Yacht Charters
Classic sailing yacht — Peconic and Gardiners Bay private charters
Sag Harbor, NY 11963
Price: $$$$ private charter
Catboat Sailing Sag Harbor
Traditional gaff-rigged catboat — most photogenic option on Sag Harbor Bay
Long Wharf, Sag Harbor, NY 11963
Price: $150-200/person, 90-min daysail
Mon Tiki Largo
Hand-built sailing catamaran — daily Sag Harbor Bay daysails and sunset sails
Long Wharf, Sag Harbor, NY 11963
Price: $95/person sunset sail