If you’ve ever dreamed of spending a weekend in the Hamptons—sipping wine, lounging on gorgeous beaches, and pretending you belong in a Nancy Meyers movie—this is your perfect itinerary.
This part of Long Island is packed with everything from historic seaside villages to gorgeous beaches and some of the best lobster rolls you’ll ever eat.
Whether you’re here for the fancy vibes, the laid-back beaches, or just to see what all the hype is about, we’ve got the ultimate weekend plan to make you feel like a Hamptons pro.
1. Coopers Beach
Coopers Beach in Southampton is a dreamy stretch of soft, white sand backed by rolling dunes and dotted with fancy mansions that scream ‘old-money’.
Located right off Meadow Lane, this beach is famous for its gentle waves, lifeguard-patrolled swimming areas, and a concession stand offering various snacks.
Parking is pricey (we’re talking $50 a day in peak season), but if you bike in or snag a Southampton Village beach permit, you’ll get to enjoy one of the most beautiful—and bougie—beaches in the Hamptons without breaking the bank.
2. Parrish Art Museum
If you need a break from the sand but still want something easy on the eyes, the Parrish Art Museum is the best place to go next.
Sitting right off Montauk Highway in Water Mill, this sleek, barn-like building is packed with incredible works from Long Island artists, including pieces by Jackson Pollock and Willem de Kooning.
The museum’s massive windows and outdoor sculptures make the whole place feel like a work of art, so even if you’re just here for the aesthetic, it’s totally worth the stop.
3. Bridge Gardens, Bridgehampton
For a total change of pace, Bridge Gardens in Bridgehampton is a quiet little oasis where you can slow down and pretend you have your life together.
This five-acre gem started as a private herb garden but has grown into a stunning mix of manicured hedges, colorful flower beds, and a unique four-quadrant herb garden.
It’s the perfect spot to wander, picnic, or just flex your plant knowledge while pretending you totally knew what bee balm looked like before today.
4. Wölffer Estate Vineyard
If all that garden strolling has you craving a drink, Wölffer Estate Vineyard in Sagaponack is the place to be.
This picture-perfect winery is famous for its rosé (you’ve definitely seen the iconic bottles on Instagram), but their crisp whites and bold reds are just as good.
Grab a glass, snag a seat on the outdoor terrace, and soak up those vineyard views—bonus points if you time it for sunset, when everything turns golden and ridiculously gorgeous.
5. Sag Harbor
Once you’ve had your fill of wine and scenic views, head to Sag Harbor, the cutest waterfront town you’ll ever see.
This former whaling village is packed with historic charm, unique boutiques, and seafood spots where the lobster rolls are chef’s kiss perfection.
Stroll down Main Street, check out the old-school windmill by the marina, and if you’re feeling fancy, hop on a boat tour to see the Hamptons from the water—because why not?
6. LongHouse Reserve
If you’re in the mood for something a little artsy and a little outdoorsy, LongHouse Reserve in East Hampton is a must.
This 16-acre sculpture garden feels like a treasure hunt for giant, mind-blowing art pieces, with works by legends like Yoko Ono and Willem de Kooning hiding among the trees and flowers.
Wander the winding paths, snap a pic with the striking white “Fly’s Eye Dome,” and soak up the creative energy that will make you want to redecorate your entire apartment.
7. East Hampton Village
After soaking up all that art, head to East Hampton Village, where everything looks straight out of a movie.
The tree-lined streets are packed with high-end boutiques, charming cafés, and historic homes that date back to the late 1600s.
Grab an iced latte from The Golden Pear, window-shop your way down Main Street, and if you’re feeling extra, swing by the Maidstone for a cocktail at its stylish bar.
8. Navy Beach Pier
If you want to explore somewhere that feels effortlessly cool, Navy Beach Pier in Montauk is the spot.
This laid-back, tucked-away stretch of sand is famous for its unreal sunsets, waterfront dining, and history—it was part of the U.S. Navy training and torpedo testing area during World War II.
Kick back with a cocktail at Navy Beach Restaurant, watch the boats drift by, and soak up that perfect end-of-day glow that makes Montauk feel like pure magic.
9. Shadmoor State Park
If you’re up for a little adventure, Shadmoor State Park in Montauk is the perfect place to stretch your legs and soak in some epic coastal views.
This 99-acre park is all dramatic cliffs, sandy trails, and hidden WWII bunkers, plus it’s one of the best spots around for catching sight of ospreys soaring overhead.
Take the short hike to the bluffs, snap a pic of the endless Atlantic, and let the salty breeze remind you why Montauk is always worth the extra drive.
10. Montauk Point Lighthouse
And if you’re making it all the way to Montauk, you have to visit the Montauk Point Lighthouse—it’s basically the grand finale of any Hamptons trip.
Built in 1796 (yes, it’s that old), this iconic lighthouse sits at the very tip of Long Island, where the Atlantic crashes against rocky shores in the most dramatic way possible.
Climb to the top for insane panoramic views, wander through the museum, and take a moment to appreciate the fact that George Washington himself approved this place—because that’s some serious history.
(Please note that the Montauk Point Lighthouse Museum closes over winter and reopens in March.)
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