The Hamptons in 3 days

Long Island's storied string of beach villages, farm stands, and summer sophistication. Best time to visit: June to early September; May and late September for quieter visits. Average daily budget: $250 to $500.

Day 1, Get oriented

Base: East Hampton, The most polished village, with high-end boutiques, historic Main Street, and Main Beach, regularly ranked among America's best.

Morning: Browse the Sag Harbor farmers market. Saturday morning market with local produce, oysters, and baked goods by the harbor.

Afternoon: Explore East Hampton, The most polished village, with high-end boutiques, historic Main Street, and Main Beach, regularly ranked among America's best.

Evening: Watch sunset at Navy Beach. Montauk's beloved sunset spot with picnic tables right on Fort Pond Bay.

Eat: The Lobster Roll (LUNCH), the roadside Amagansett classic since 1965

Day 2, Go deeper

Base: Sag Harbor, A former whaling port with a literary soul, indie bookshops, and a relaxed harborfront scene.

Morning: Swim at Main Beach. East Hampton's iconic stretch of sand, consistently rated one of the top beaches in the United States.

Afternoon: Explore Sag Harbor, A former whaling port with a literary soul, indie bookshops, and a relaxed harborfront scene.

Evening: Visit the Montauk Point Lighthouse. Climb the 1796 lighthouse commissioned under George Washington at Long Island's eastern tip.

Eat: Nick & Toni's, East Hampton's farm-to-table institution

Day 3, Hidden side

Base: Montauk, The laid-back surf town at the island's tip, with a lighthouse, fishing boats, and a younger crowd.

Morning: Taste at Wölffer Estate Vineyard. Sip rosé on the terrace of the Hamptons' most famous winery in Sagaponack.

Afternoon: Explore Montauk, The laid-back surf town at the island's tip, with a lighthouse, fishing boats, and a younger crowd.

Evening: Walk the Pollock-Krasner House. Tour the Springs studio where Jackson Pollock created his drip paintings, floorboards still splattered.

Eat: Duryea's, dockside lobster and rosé in Montauk

Hidden gems

Coopers Beach in Southampton, often emptier than Main Beach and equally beautiful
The LongHouse Reserve sculpture gardens in East Hampton
Gosman's Dock in Montauk for fresh seafood on the working harbor
Cedar Point County Park trails with views of Gardiners Bay

Getting around

The Hampton Jitney (bus) and LIRR (train) run from Manhattan in 2 to 3.5 hours; the summer Friday LIRR 'Cannonball' is fastest. A car is strongly recommended once there, villages are spread out and rideshares are scarce and surge-priced in summer. Bikes work well within individual villages.

Safety

The Hamptons are very safe. Ocean rip currents are the main hazard, swim near lifeguards. Ticks carrying Lyme disease are common in grassy and wooded areas; use repellent and check yourself after hikes. Summer traffic on Route 27 is notorious, plan extra travel time.

The Hamptons in 5 days | The Hamptons in 7 days | Full The Hamptons guide