Weekend getaway from New York · #2 of 10
The Hamptons & Montauk
Long Island's fabled South Fork: white-sand beaches at Southampton and East Hampton, art stops in Bridgehampton, Sag Harbor's marina, and Montauk's surf breaks and lighthouse at the very end.
Think white-sand beaches, local art spaces, and salty harbor towns, all leading to Montauk: the ultimate surfy, laid-back escape. Day one is a slow crawl through historic villages; day two is all about Montauk's wild waves, lighthouse vibes, and legendary sunset drinks.
Getting there
The classic car-free route: roughly 2.5 hours to Southampton and just over 3 to Montauk. Note that summer weekend trains get packed, so get to the station early to claim a seat.
A plush coach bus that drops you right in the center of the villages. Travel time is around 2.5 to 3.5 hours, but beware: summer Friday traffic on the LIE can easily tack on extra hours.
Day 1
Sandy shores, local galleries, and harbor walks- 18:00 AMDrive
Head east on the LIRR or Jitney
Ditch the city early to outrun the beach-bound crowds. Think of the train or bus ride as your personal decompression chamber before stepping into chill South Fork time.
📍 Penn Station, New York
Tip · Book those Jitney tickets weeks in advance if you're traveling during peak summer weekends.
- 210:30 AMActivity
Morning at Coopers Beach
Southampton's crown jewel: powdery white sand backed by wild dunes and grand shingled estates. Best of all, it is the rare Hamptons beach you can actually visit without a resident parking permit.
📍 Coopers Beach, Southampton
Tip · No car? No problem. Grab a quick cab from the Southampton train station.
- 312:30 PMFood
Lunch in Southampton Village
Stroll the boutique-filled lanes before grabbing a casual bite. Fellingham's is the ultimate locals' pub for a cold draft and a solid burger, totally free of Hamptons pretense.
📍 Southampton Village, Southampton
- 42:00 PMSight
Parrish Art Museum
A sleek, barn-inspired space in Water Mill celebrating the east end's legendary light and the artists who chased it. It is the perfect quick culture hit between beach sessions.
📍 Parrish Art Museum, Water Mill
- 53:30 PMSight
Dan Flavin Art Institute
Tucked inside a former Bridgehampton firehouse, this free Dia outpost houses Dan Flavin's glowing fluorescent-light installations. It is small, wonderfully trippy, and absolutely worth the stop.
📍 Dan Flavin Art Institute, Bridgehampton
Tip · Admission is totally free, but check their website for seasonal hours before you head over.
- 65:00 PMActivity
Golden hour in Sag Harbor
This historic whaling port is now a lively yachting hub made for lazy afternoon wanders. Explore the docks, flip through pages at the local bookshops, and check out the main street boutiques.
📍 Sag Harbor, New York
- 77:30 PMFood
Dinner in Sag Harbor or East Hampton
You can't go wrong here: grab local oysters and chowder right on the Sag Harbor waterfront, or opt for a sleek, farm-to-table spot tucked off East Hampton's historic Main Street.
📍 Main Street, East Hampton
Tip · Peak summer tables are a hot commodity, so lock in your dinner reservations by midweek.
- 8NightStay
Check in at the Reform Club
A gorgeous Amagansett retreat featuring cozy wood-burning fireplaces, massive marble tubs, and total privacy behind lush hedges. It is the ultimate launchpad between East Hampton and Montauk.
📍 Reform Club, Amagansett
Day 2
Montauk magic: clean waves, historic bluffs, and sunset drinks- 98:30 AMFood
Breakfast in Amagansett
Fuel up with a hot cup of coffee and a casual bite near the beautiful village green before making the final, scenic run out to the edge of the island.
📍 Amagansett, New York
- 109:30 AMActivity
Surf morning at Ditch Plains
Ready to catch some waves? Grab a rental board and wetsuit from the legendary Air and Speed Surf Shop in town, then paddle out at Ditch Plains, the area's premier longboard break.
📍 Ditch Plains Beach, Montauk
Tip · New to the board? Lock in a private lesson with the local legends at Corey's Wave.
- 1112:30 PMFood
Lobster roll on the Napeague stretch
Pull over at the iconic 'LUNCH' sign on the Napeague stretch. This classic, retro roadside shack serves up the quintessential, no-nonsense lobster roll you came all this way for.
📍 The Lobster Roll Restaurant, Amagansett
- 122:00 PMSight
Montauk Point Lighthouse
Stand at the edge of New York: the state's oldest lighthouse marks the wild tip of Long Island. Climb up for endless ocean vistas, or watch local surfcasters brave the rocky shoreline below.
📍 Montauk Point Lighthouse, Montauk
- 133:30 PMActivity
Bluffs and bunkers at Camp Hero
Right next door, Camp Hero serves up dramatic, windswept ocean cliffs alongside the eerie, abandoned radar towers and concrete bunkers of a vintage Cold War military base.
📍 Camp Hero State Park, Montauk
- 145:00 PMFood
Pint at Montauk Brewing Company
Head back to the village and join the sun-kissed, post-surf crowd at this relaxed taproom. Grab a cold, local draft and check out the neighboring surf shops and boutiques.
📍 Montauk Brewing Company, Montauk
- 156:30 PMSight
Sunset at the Montauket
This legendary local dive on Fort Pond Bay is the place to be. Grab a plastic cup of beer, find a spot on the lawn, and watch the sun sink directly into the water.
📍 The Montauket, Montauk
Tip · Get there early to snag a prime spot along the lawn railing before the show starts.
- 168:30 PMDrive
Ride home from The End
Hop on the evening train or the Jitney back to the city. Sunday nights are notoriously busy, so secure your spot early and ease back into the Manhattan mindset.
📍 Montauk Station, Montauk
Where to eat
That legendary, photo-ready 'LUNCH' sign on the highway. They've been serving the area's benchmark lobster roll since the swingin' sixties.
A super-relaxed local taproom right in town. Order a Wave Chaser IPA, which you'll see on tap all over the island for good reason.
A beloved, no-nonsense local pub in Southampton. Perfect for a juicy burger and an ice-cold pint after a long day in the sand.
The holy grail of East End sunsets. Grab a cold draft, find a spot on the grass, and watch the sun dip right into Fort Pond Bay.
When to go
The absolute height of the season. Expect perfect beach days, massive crowds, and top prices. You'll need to book your stays and bus seats weeks in advance.
Our favorite time to visit. The ocean stays warm well into September, the crowds clear out, booking dinner is a breeze, and the surf really starts pumping.
Quiet, chilly, and beautifully wild. While many hotels and eateries shut down or trim their hours, you'll have the gorgeous, windswept beaches entirely to yourself.
Good to know
- Ditch the car keys: take the train or the Jitney out, then rely on local cabs or rideshares to hop between the beaches and village centers.
- Keep beach permits in mind: Coopers Beach welcomes everyone, while East Hampton's Main Beach requires paid parking, and Kirk Park is the go-to public stretch in Montauk.
- Beat the crawl: Friday afternoon traffic on Route 27 is legendary for all the wrong reasons, so head out early Friday morning or make the trek Thursday night.
- Planning a summer weekend getaway? Make sure to lock down your lodging and restaurant reservations far in advance.
