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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Filters21 adventures
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. There is no commercial operator — you buy the permit at Town Hall, walk out at dead low tide, and rake your dinner.
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 thermals build by mid-morning and the sand bottom is forgiving when a beginner gets dragged.
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 fetch keeps the chop low enough for beginners to plane on a bigger sail.
Beginner–AdvancedMay–Octoberhalf day - $$
Montauk Sportfishing Charter
Montauk · On the Water
Montauk calls itself the sport-fishing capital of the world and the West Lake Drive harbor backs it up: open party boats from $75 a head for a half day, multi-day offshore trips chasing tuna and tilefish, and thirteen private charter boats berthed at Star Island, each with its captain's phone number published.
Beginner–AdvancedMay–Novemberfull day 
Photo: Michael Galpert (CC BY 2.0), via Flickr $Surfing at Ditch Plains
Montauk · On the Water
The most reliable beach break on the East End and the spiritual home of New York surfing — long, soft-shouldered rights that peel toward the Ditch jetty on a SW swell. Four operators teach here, with shuttle pickups from Wainscott to Edgemere.
Beginner–AdvancedApril–November90 min- $$
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 and humpback whales, plus dolphins, feeding on bait fish off Montauk from late May through September. $100 adult, $55 for kids 5-12, free under 5; book directly through Viking Fleet, the operator CRESLI sails with.
BeginnerMay–September5-6 hours - $$$
Sailing Charter Sag Harbor
Sag Harbor · On the Water
Sag Harbor Sailing has been putting people on 23-foot Pearson Ensigns since 1997, and they are real sailboats — no engine noise, no party barge, six people maximum. Take a licensed captain or take the tiller yourself; the day rate is the same either way. The boats live at the Yacht Hampton Boating Center on Pine Neck Avenue, a few minutes west of the village.
BeginnerMay–Octoberhalf day - Free
Jet Ski Rental Three Mile Harbor
Springs · On the Water
Nobody rents a jet ski on Three Mile Harbor right now — the two operators nearest the water here run wakeboard boats and slips instead. The harbour itself is the gentlest PWC water on the South Fork if you bring your own: protected from Atlantic chop, with an easy run out to Gardiners Bay. New York requires a PWC safety certificate for everyone born after 1996.
Beginner–IntermediateJune–September90 min - Free
Kayak Accabonac Harbor
Springs · On the Water
Accabonac is the most undeveloped harbor on the South Fork — osprey, oystercatchers, and the salt marsh that inspired Pollock and Krasner. Glass at sunrise, raked by southwesterlies after lunch.
Beginner–IntermediateApril–Octoberhalf day- Peconic Land Trust+1-631-283-3195
- Khanh Sports — Kayak Rental+1-631-324-1077
- Louse Point Town Launch (BYO)
- $$
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 easy parking at the public ramp. Sunrise sessions are a Springs ritual.
Beginner–IntermediateMay–October90 min
On Land · 5
- 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. The eastern 30 miles, from Hither Hills to the lighthouse, are the wildest section and the cleanest expression of moraine, kettle hole, and oceanfront bluff.
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 class or a pass and expect to leave a little muddy. Sessions run at Hero Beach Club and Hither Hills General through summer 2026.
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 it still runs guided rides out along the Block Island Sound shore. Riding is western, groups are small, and guides match you to a horse — pony rides from five, short trail rides from six, the beach ride from eight.
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. The 137-step climb up the spiral iron staircase ends at the original Fresnel lens room with a 360 view of the Atlantic, Block Island, and the Connecticut shore.
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 moraine ridge above Napeague Bay. Free, self-guided, and crowded only on the first warm Saturday of spring.
Intermediate–AdvancedMarch–Decemberhalf day
Camping · 2
- $
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 and you are oceanfront for $33 a night. Booking opens nine months out and the prime July weeks vanish in literal seconds.
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 no Atlantic surf to drown out the morning birdsong. The 1860 lighthouse offshore stopped being an island in the 1938 hurricane, which threw up the sand spit you can now walk out on.
Beginner–IntermediateApril–Novemberfull day
Wellness · 2
- 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 and shorebirds in fall, and waterfowl through winter. SoFo runs the canonical guided walks; the parking pull-off on Sagg Main Street is the standard meet-up.
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. Yoga Shanti and Mandala both run summer outdoor classes at Long Beach and Atlantic Avenue Beach respectively.
Beginner–AdvancedJune–September90 min