Everyone knows the Hamptons for the beach clubs and the traffic on Route 27 – fewer people make it out to the lighthouse at the very end of the island, or across the water to the North Fork’s quieter, cheaper wine country. This three-day loop drives the length of Long Island’s East End: Montauk’s surf and a 1796 lighthouse, Hamptons vineyards and a whaling-village stroll in Sag Harbor, a short ferry hop to Shelter Island, and a last day among the North Fork’s vineyards and Greenport’s harborfront.
Day 1Montauk & the Point
The drive out from New York City takes about two and a half to three hours via Sunrise Highway/Route 27 – plan to leave early and make the lighthouse the first stop before the day-trip crowds arrive.
🏞️ Montauk Point Lighthouse
Seasonal hours (check calendar) · $15 USD/person tower climb
New York’s oldest lighthouse, commissioned by George Washington in 1792 and first lit in 1796. Climb the 137 steps to the top for views over the Atlantic, or just walk the bluffs below – a favorite spot for seal-watching in winter.
Montauk Point Lighthouse · montauklighthouse.com
🦞 Lunch — Clam Bar at Napeague
Seasonal (spring-fall) · $20-35 USD/person
A roadside shack on Montauk Highway that’s been a Hamptons lobster-roll institution for decades – fried clams, chowder, and a lobster roll eaten at a picnic table outside, no reservations and often a line.
Clam Bar at Napeague · (631) 267-6348
🏄 Afternoon — Ditch Plains Beach
Afternoon · free
Montauk’s best-known surf beach, with a lineup of longboarders most afternoons and a laid-back scene even for non-surfers – a good spot to watch the sunset over the water.
🏨 Check-In — Gurney’s Montauk Resort & Seawater Spa
Check-in 4pm · from $714 USD/night
An oceanfront resort on its own stretch of Montauk beach, with a seawater spa and several on-site restaurants – the classic Montauk splurge stay.
Gurney’s Montauk Resort & Seawater Spa · 1-631-668-2345 · gurneysresorts.com/montauk
Day 2Hamptons Wine Country to Shelter Island
Backtrack west through the Hamptons’ vineyard country and a whaling-village stop in Sag Harbor, then take the short ferry crossing to Shelter Island on the way to the North Fork.
🍇 Wine Tasting — Wölffer Estate Vineyard
Reserve ahead · tastings typically $35-50 USD/person
The Hamptons’ best-known winery, famous for its rosé and a sweeping lawn framed by a windmill-topped tasting pavilion. Reservations fill up on weekends, especially for a table on the lawn.
Wölffer Estate Vineyard · 631-537-5106 · wolffer.com
🚢 Sag Harbor Village Stroll
1-2 hours · free
A former whaling port with a walkable Main Street of 19th-century sea captains’ houses, independent bookshops, and the landmark Sag Harbor Cinema marquee – a good lunch-on-your-own stop between the vineyards and the ferry.
⛴️ Shelter Island Ferry Crossing — South Ferry
~10 minute crossing · $20 USD one-way for a car + driver
A short car ferry from North Haven across Shelter Island Sound – no reservations, first-come first-served, running continuously in season. Shelter Island itself is worth a slow drive across before picking up the North Ferry on the far side toward Greenport.
South Ferry · (631) 749-1200 · southferry.com
🏨 Check-In — Sound View Greenport
Check-in 4pm · from $477 USD/night
A Long Island Sound-front motel-turned-boutique-hotel just outside Greenport village, with a private beach and The Halyard restaurant on-site – a mellower, less expensive base than the Hamptons side of the trip.
Sound View Greenport · 631-477-1910 · soundviewgreenport.com
Day 3North Fork Wine Trail & Greenport
A slower last day among the North Fork’s vineyards – cheaper and less crowded than the Hamptons side – before a harborfront lunch in Greenport and the drive home.
🍇 Tasting — Jamesport Vineyards
Reservations required · flights from roughly $20-30 USD/person
One of the North Fork’s original wineries, housed in a restored 1800s barn, with a kitchen serving wood-fired flatbreads alongside the tasting flights. Guests must be 21+ on Friday evenings and weekends.
Jamesport Vineyards · 631-722-5256 · jamesportwines.com
⚓ Greenport Village & Harborfront
1-2 hours · free (carousel rides ~$2)
A working fishing port turned walkable village, with a restored 1920s carousel on the waterfront, tall ships docked at the pier, and a row of shops and galleries along Front Street.
🦞 Lunch — Claudio’s
Lunch · $30-50 USD/person
A Greenport waterfront landmark run by the same family since 1870, with a marina-side dining room and a more casual clam bar downstairs – the classic last stop before heading back toward the city.
Claudio’s · (631) 477-0627 · claudios.com
🚗 Drive Home
~2.5-3 hours to NYC via the LIE
Head back west on Route 25 to the Long Island Expressway – build in extra time on Sunday afternoons, when weekend-getaway traffic backs up heading into the city.
Download your itinerary here
