Not recommended for travelers with spinal injuries
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Not recommended for travelers with poor cardiovascular health
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Suitable for all physical fitness levels
Cancellation policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
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For a full refund, you must cancel at least 24 hours before the experience’s start time.
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Cut-off times are based on the experience’s local time.
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If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.
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This experience requires a minimum number of travelers. If it’s canceled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund.
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Any changes made less than 24 hours before the experience’s start time will not be accepted.
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Discover the legendary Hamptons on this self-guided tour through the oceanfront villages along the South Fork of Long Island. For centuries, these shores have drawn artists, writers, and presidents, yet the Hamptons remain rooted in a quieter history of Shinnecock native peoples, settlers, and whalers. Begin in Southampton, where white-columned estates line lanes, then drive east through farm stands and vineyards between the glamorous towns. Explore Sag Harbor's whaling heritage, stroll the tree-canopied main street of East Hampton where windmills from the 1600s still stand, and continue to wild Montauk, where a lighthouse has guarded the Atlantic since George Washington authorized its const...
Highlights
8 hours and 30 minutes
Offered in English
Free Cancellation
Mobile Ticket
8 hours and 30 minutes
Offered in English
Free Cancellation
Mobile Ticket
What's Included
Self-guided walking tour, fully on the app — explore at your own pace
NO live guide or rental equipment provided — please bring your own smartphone and headphones
Digital Map: GPS coordinates for every stop with navigation support
40 narrated stops from Westhampton to Montauk and beyond
Private transportation
Admission fees, live guide, headphones, transport, parking, food/drinks, internet access and rentals
Meeting Points
Departure
Jobs Lane
This is a self-guided app-based tour with no in-person guide or fixed meeting point. Your access code is already on your ticket (below the barcode) — enter it in the CloudGuide app to start at the suggested location, or any stop on the route, in the order that suits you best.
Return
Itinerary
1
Parrish Art Museum
Pass by the Parrish Art Museum in Water Mill, the East End's premier art institution, known for its collection of works by artists who lived and worked in the Hamptons, including William Merritt Chase and Fairfield Porter.
2
Cooper's Beach
Cooper's Beach is one of the most beautiful stretches of sand on the Eastern Seaboard, consistently ranked among the top beaches in the United States. Alongside it runs Meadow Lane, one of the most expensive addresses in the country.
1 hour
3
Wolffer Estate Vineyard
Wolffer Estate Vineyard is, by almost any measure, the premier winery in the Hamptons - a stunning fifty-five-acre property that has done more than any other to put Long Island wine on the international map.
4
Sag Harbor
Sag Harbor is one of the most enchanting small villages on the Eastern Seaboard - a real place with deep roots, genuine character, and a soul forged by centuries of remarkable whaling history.
1 hour and 30 minutes
5
Pollock-Krasner House and Study Center
The Pollock-Krasner House and Study Center in Springs preserves the home and studio of Jackson Pollock and Lee Krasner, two towering figures of twentieth-century art who lived and worked here.
6
Guild Hall
Guild Hall is the cultural heart of East Hampton. Since 1931, this Main Street building has served as gallery, theater, and community gathering place, establishing the village as a genuine cultural destination.
1 hour
7
Main Beach
Main Beach in East Hampton is an icon - considered by many the most famous beach in the Hamptons and a strong contender for the most famous in the Northeastern United States.
1 hour
8
Montauk Point Lighthouse
At the easternmost tip of Long Island stands the Montauk Point Lighthouse, one of the most iconic structures in New York State, where history, natural beauty, and raw oceanic power converge.
9
Ditch Plains
Ditch Plains is the most famous surf beach in the Hamptons, where East Coast wave-riding culture meets the salt-sprayed energy of Montauk.
1 hour
10
Shelter Island
Shelter Island sits in the middle of Peconic Bay, nestled between the North and South Forks like a hidden gem, and is home to the vast Mashomack Preserve.
1 hour
Discover The Hamptons: A Self-Guided Tour
Water Mill
About
Discover the legendary Hamptons on this self-guided tour through the oceanfront villages along the South Fork of Long Island. For centuries, these shores have drawn artists, writers, and presidents, yet the Hamptons remain rooted in a quieter history of Shinnecock native peoples, settlers, and whalers. Begin in Southampton, where white-columned estates line lanes, then drive east through farm stands and vineyards between the glamorous towns. Explore Sag Harbor's whaling heritage, stroll the tree-canopied main street of East Hampton where windmills from the 1600s still stand, and continue to wild Montauk, where a lighthouse has guarded the Atlantic since George Washington authorized its const...
Highlights
8 hours and 30 minutes
Offered in English
Free Cancellation
Mobile Ticket
8 hours and 30 minutes
Offered in English
Free Cancellation
Mobile Ticket
What's Included
Self-guided walking tour, fully on the app — explore at your own pace
NO live guide or rental equipment provided — please bring your own smartphone and headphones
Digital Map: GPS coordinates for every stop with navigation support
40 narrated stops from Westhampton to Montauk and beyond
Private transportation
Admission fees, live guide, headphones, transport, parking, food/drinks, internet access and rentals
Meeting Points
Departure
Jobs Lane
This is a self-guided app-based tour with no in-person guide or fixed meeting point. Your access code is already on your ticket (below the barcode) — enter it in the CloudGuide app to start at the suggested location, or any stop on the route, in the order that suits you best.
