Discover The Hamptons: A Self-Guided Tour

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.

1. 1

   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.

2. 2

   Cooper's Beach

   1 hour

   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.

3. 3

   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.

4. 4

   Sag Harbor

   1.5 hours

   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.

5. 5

   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.

6. 6

   Guild Hall

   1 hour

   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.

7. 7

   Main Beach

   1 hour

   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.

8. 8

   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.

9. 9

   Ditch Plains

   1 hour

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

10. 10

    Shelter Island

    1 hour

    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.

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

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