Photography by Kathleen Gildea

Similar to Northerners heading up to their lake houses on weekends, New Yorkers migrate east to the beach. Spread across the South Fork of Long Island is one charming town after the next. When visiting, it can be overwhelming to decide where to explore, but rest assured that there isn’t a bad choice, from Amagansett to Bridgehampton to East Hampton to Montauk to Sag Harbor to South Hampton to Westhampton Beach. Each town has its own charm, excellent dining and great shopping. Here are our favorite three ways to artfully experience the Hamptons.


Montauk

The furthest point east on Long Island is Montauk — the end of the world. This fishing and surfing town is quickly becoming an it destination. Montauk has a laidback vibe with hints of a West Coast feel. 

Stay

Gurney’s Montauk
There’s no better spot in Montauk than Gurney’s. The property stretches across the pristine beach and offers private, king-sized beach beds for rent perfect for soaking up the sun.

Eat + Drink

Gosman’s
Watch the fishing boat traffic coming in and out while noshing on a famous lobster roll. This gem is off the beaten path, but you’ll quickly see why regulars love it.

Navy Beach
For cocktails and prime sunset views, Navy Beach is the place to go. It has vintage nautical decor inside and bean bag chairs outside along the beach. Make a reservation or chances are you won’t even be able to get a parking spot.

The Surf Lodge
Live music and après-beach drinks? It doesn’t get much better than this. The summer’s hottest music lineups can be heard right here.

Do

Montauk Lighthouse
The famous Montauk Lighthouse is a National Historic Landmark that played an important role in American maritime history. The view is worth the 137+ steps. 


Sag Harbor

Sag Harbor is quietly tucked away but ideally located. Chances are you won’t want to leave this quaint town, but it’s an easy drive to the Hampton villages and Shelter Island.

Stay

Baron’s Cove
This boutique hotel boasts comfortable, chic rooms that face the harbor. Walk by foot into town or hop on one of the provided bikes to venture to the nearby beach.

Eat + Drink 

Dopo La Spiaggia
This is some of the best Italian food you’ll find on the East End. The delicious fare and cozy ambiance lure celebrities here on a regular basis. Make a reservation and keep your fingers crossed for a Jimmy Fallon sighting.

Page at 63 Main
Located right on Main Street, Page is a fresh local spot. The restaurant provides a true farm-to-table taste for Long Island’s East End.

Wolffer Estate Vineyard
A visit to Wolffer Estate is an easy alternative to a trip to Tuscany, replete with the same elegance and quality views. This is an essential stop for a glass of wine or a rosé flight. 

Do 

Yoga Shanti
Daily classes for all skill levels are offered at the home studio of famous yogi Colleen Saidman Yee. If you don’t get the chance to practice with her, get your hands on her book, Yoga for Life, and you’ll quickly understand the reasoning for her huge fan base. 


Westhampton Beach

Stay

The Ocean Resort at Bath & Tennis
Found on famous Dune Road is dream home after dream home as well as the Ocean Resort at Bath & Tennis. This simple beachfront hotel allows access to a private pool, the beach and tennis courts. Bonus: It’s just a short drive, walk or bike into town.

Eat + Drink 

Beach Bakery
In downtown Westhampton Beach, you’ll smell sweets baking at beloved Beach Bakery. New York’s famous black and white cookies are made fresh daily. Pick up a dozen first thing in the morning — it should last you a few hours.

Dockers Waterside
Everything about this all-time favorite eatery screams Hamptons. Order sushi or surf and turf. Opt for a table on the deck for a nice breeze and Instagram-worthy views.

John Scott’s Surf Shack
This is the place to roll up to donning a swimsuit cover-up and sandy toes. Beachcombers come directly from their 9-to-5 seaside day to fuel up on tasty food and catch the sunset.

Do 

Island Surf
Open seven days a week, this shop will deliver kayaks and standup paddleboards directly to your Westhampton Beach location. Feeling ambitious? Sign up for surfing school for a private lesson with a local.