Discover The Hamptons: A Self-Guided Tour

Duration8h 30m

Free cancellationFull refund up to 24 hours before

Instant confirmationYour booking is confirmed right away

TicketMobile or paper ticket accepted

LanguagesEnglish

Private tourOnly your group will participate

Overview

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 construction in 1796. Along the way, encounter world-class beaches, art museums, and nature preserves that make the Hamptons far more than a celebrity playground. This tour reveals the authentic character beneath the glitz — a place shaped by the sea, the land, and 4 centuries of American stories.

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

What to expect

Parrish Art Museum
Pass by

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.
Cooper's Beach
1h

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.
Wolffer Estate Vineyard
Pass by

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.
Sag Harbor
1h 30m

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.
Pollock-Krasner House and Study Center
Pass by

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.
Guild Hall
1h

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.
Main Beach
1h

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.
Montauk Point Lighthouse
Pass by

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.
Ditch Plains
1h

Ditch Plains is the most famous surf beach in the Hamptons, where East Coast wave-riding culture meets the salt-sprayed energy of Montauk.
Shelter Island
1h

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.

Meeting and pickup

Meeting point

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.

End point

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.

Additional information

Not recommended for travelers with spinal injuries
Not recommended for travelers with poor cardiovascular health
Suitable for all physical fitness levels

Cancellation policy

For a full refund, cancel at least 24 hours before the scheduled departure time.