Hamptons Adventure
Surf, sail, hike, climb, fish, camp, skydive: 21 ways to get outside on the East End, with real operators and real phone numbers.
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20 adventures
On the Water · 10
- Free
Clamming Napeague Bay
Amagansett · On the Water
Napeague's tidal flats are East Hampton's most productive littleneck and cherrystone grounds.
BeginnerSeptember–Aprilhalf daySelf-guidedNo commercial operator — permit or self-guided
- Free
Kitesurfing Napeague Bay
Amagansett · On the Water
Napeague Harbor's flat, knee-deep bay is the safest classroom on the East Coast for learning to kite — predictable SW…
Intermediate–AdvancedMay–Octoberhalf day - Free
Windsurfing Napeague
Amagansett · On the Water
The East End's classic windsurf spot — Napeague Harbor catches the same SW thermal as the kitesurfers but the smaller…
Beginner–AdvancedMay–Octoberhalf day - $$
Montauk Sportfishing Charter
Montauk · On the Water
Montauk calls itself the sport-fishing capital of the world and the West Lake Drive harbor backs it up: open party…
Beginner–AdvancedMay–Novemberfull day 
Photo: Michael Galpert (CC BY 2.0), via Flickr $Surfing at Ditch Plains
Montauk · On the Water
The most reliable beach break on the East End and the spiritual home of New York surfing — long, soft-shouldered…
Beginner–AdvancedApril–November90 min
Show 16 more adventures
- $$
Whale Watching
Montauk · On the Water
CRESLI naturalists have narrated whale watches aboard the Viking Fleet out of Montauk Harbor for 31 seasons — fin, minke…
BeginnerMay–September5-6 hours - $$$
Sailing Charter Sag Harbor
Sag Harbor · On the Water
Sag Harbor Sailing has been putting people on 23-foot Pearson Ensigns since 1997, and they are real sailboats — no…
BeginnerMay–Octoberhalf day - Free
Jet Ski Rental Three Mile Harbor
Springs · On the Water
Nobody rents a jet ski on Three Mile Harbor right now — the two operators nearest the water here run…
Beginner–IntermediateJune–September90 min - Free
Kayak Accabonac Harbor
Springs · On the Water
Accabonac is the most undeveloped harbor on the South Fork — osprey, oystercatchers, and the salt marsh that inspired Pollock…
Beginner–IntermediateApril–Octoberhalf day- Peconic Land Trust+1-631-283-3195
- Khanh Sports — Kayak Rental+1-631-324-1077
- Louse Point Town Launch (BYO)
- $$
Stand-Up Paddleboard Three Mile Harbor
Springs · On the Water
Three Mile Harbor is the calmest paddleboard water on the South Fork — protected from every direction, sand bottom, and…
Beginner–IntermediateMay–October90 min
On Land ·
- Free
Paumanok Path Hike
East Hampton · On Land
The Paumanok Path is Long Island's longest continuous hiking trail — 125 miles from Rocky Point to Montauk Point.
Beginner–AdvancedYear-roundfull day Clay Camp - Drop-in Pottery Wheel
Montauk · On Land
Drop-in pottery-wheel sessions on the beach side of Montauk - no experience needed, clay and wheel provided, book a single…
Beginner
Photo: Americasroof (CC BY-SA 2.5), via Wikimedia Commons $Deep Hollow Ranch Beach Ride
Montauk · On Land
Deep Hollow bills itself as the birthplace of the American cowboy and the oldest working ranch in the country, and…
Beginner–IntermediateApril–November90 min
Photo: Bruce Adler (CC BY-SA 4.0), via Wikimedia Commons $Montauk Lighthouse Climb
Montauk · On Land
Commissioned by George Washington in 1792 and still warning mariners off the Block Island Sound shoals 230+ years later.
BeginnerYear-round90 min- Free
Mountain Biking Hither Woods
Montauk · On Land
Hither Woods is the East End's only legitimate singletrack — fast flowing rollers through scrub oak, kettle holes, and the…
Intermediate–AdvancedMarch–Decemberhalf day
Camping ·
- $
Hither Hills Oceanfront Camping
Montauk · Camping
189 sites strung along a half-mile of South Atlantic beach — pull a camp chair onto the sand at sunset…
Beginner–IntermediateApril–Novemberfull day 
Photo: Americasroof (CC BY-SA 2.5), via Wikimedia Commons $Cedar Point Camping
Springs · Camping
Cedar Point is the bayside answer to Hither Hills — 607 acres of pitch pine on Gardiners Bay, and almost…
Beginner–IntermediateApril–Novemberfull day
Wellness ·
- Free
Birding Tour Sagg Pond
Sagaponack · Wellness
Sagg Pond is a brackish coastal pond ringed by farm fields and Atlantic dune — a migration funnel for raptors…
Beginner–AdvancedSeptember–Mayhalf day - $
Sunrise Beach Yoga
Sag Harbor · Wellness
Sunrise mat on the sand, sun salutations into the Atlantic — the canonical East End yoga ritual.
Beginner–AdvancedJune–September90 min