Hamptons Weekend Guide (2025)

Your Guide to a Weekend in the Hamptons (2025)

Planning a summer weekend in the Hamptons? This 2025 guide has everything you need—where to stay, what to eat, and how to plan the perfect three-day trip. From coffee in Sag Harbor to beach sunsets in Montauk, here’s exactly how to do the Hamptons like someone who actually spends weekends out east.

Where Are the Hamptons?

Situated on Long Island’s South Fork, the Hamptons are a collection of several charming towns, including East Hampton, Southampton, Westhampton, and Bridgehampton. Known for beaches, farmers markets, and chic summer style, they’re the perfect destination for a long weekend getaway from NYC.

How to Get to the Hamptons from NYC

Getting to the Hamptons from NYC can be a breeze, or it might turn into a bit of an adventure, depending on the season and time of day. Here’s how I recommend getting out east, whether you’re leaving from the city or flying in.

By Car: The most flexible option. From NYC, take the LIE (I-495) to Route 27 East. If you live in the city and don’t have a car, I highly recommend renting through Turo. We’ve had really great experiences renting with them!
By Train: The Long Island Rail Road (LIRR) offers service to East Hampton, Southampton, and Montauk. Trains from Penn Station take 2–3 hours. You can hop off and on at stops like East Hampton, Southampton, and Montauk.
By Bus: The Hampton Jitney and Luxury Liner buses run daily between Manhattan and the Hamptons. Expect 2.5–4 hours depending on traffic.

Pro Tip: Leave early in the morning or late in the evening to avoid traffic. And if you can, go midweek (Monday–Thursday) for easier reservations and less crowding.

Best Time to Visit the Hamptons

Weekdays: For smoother traffic and better chances of snagging accommodations and restaurant reservations, opt for a weekday escape (Monday to Thursday).

Early Mornings or Late Evenings: Avoid traffic by hitting the road early in the morning or later in the evening. A 7 AM departure helps dodge city traffic.

Late Spring & Early Fall: Thinking about planning your getaway for late spring or early fall? Smart move! The weather is still delightful, but you’ll find thinner crowds compared to the bustling summer months. Plus, Hamptons hotel prices are significantly lower during this time, making it an even better deal.

Towns in the Hamptons

Each town in the Hamptons has its own personality. Here’s a quick breakdown of where to go based on your vibe:

Southampton

Polished, classic, and effortlessly chic. Southampton is where you’ll find designer boutiques, manicured beaches, and white-linen brunch spots that feel straight out of a Nancy Meyers movie.

Bridgehampton

Think farmers market mornings and boutique browsing in the afternoon. Bridgehampton is the sweet spot between rustic charm and refined living. You’ll find local farm stands, equestrian estates, and some of the best hidden-gem restaurants out east.

East Hampton

The scene is upscale but never over-the-top. East Hampton offers curated shops, tucked-away art galleries, and stunning homes you’ll want to Pinterest immediately. Come here for window shopping, gallery hopping, and the occasional celeb sighting.

Amagansett

Low-key and lovely. Amagansett has that under-the-radar energy with local coffee shops, chic but unpretentious boutiques, and farm stands around every corner. The beaches are wide, quiet, and just far enough from the buzz.

Sag Harbor

This town feels like a storybook coastal village, always buzzing with visitors and locals. Stroll the harbor, pop into indie bookstores, and grab some oysters with a view.

Montauk

Montauk is summer energy turned all the way up. It’s laid-back but luxe, with surfers by day, DJs by night, and some of the best beachfront stays on the East Coast. Come for the lobster rolls, sunset bonfires, and chill beach vibes.

Westhampton Beach

Westhampton is where families come to unwind. It’s relaxed, easygoing, and super walkable with a charming Main Street full of cafes, ice cream shops, and local boutiques.

Water Mill

Quiet, artsy, and scenic. Water Mill is often overlooked, but it’s home to outdoor art spaces and the iconic Parrish Art Museum. Perfect for nature lovers or anyone looking to slow down and take in the views.

Where to Eat in the Hamptons (2025)

When it comes to dining in the Hamptons, there’s no shortage of coastal spots to indulge in. These are the spots that locals and regulars book way in advance, and for good reason:

Duryea’s Lobster Deck (Montauk): Always my first stop. Order the lobster cobb salad, a side of fries, and a bottle of rosé. Grab a table overlooking the bay and stay for the sunset.
Bostwick’s (East Hampton): My forever favorite. Their baja fish tacos, clam chowder, and buttered lobster roll are what summer dreams are made of.
Sen (Sag Harbor): Elevated sushi in a cozy, wood-paneled space. Great for a slower-paced dinner after shopping in town.
Camp Rubirosa (East Hampton): The team behind NYC’s Rubirosa introduces a summer pop-up featuring their signature pizzas and handmade pastas, bringing a slice of the city to the Hamptons.
Almond (Bridgehampton): Cozy, creative, seasonal. The kind of place where the bartender remembers your order.

Whether you’re grabbing lobster rolls in flip-flops or getting dressed up for oysters and cocktails, there’s a spot for every kind of mood out east. Check out my full guide on what to order at my favorite restaurants in the Hamptons here.

Whether you’re searching for seafood with a view, a farm-to-table experience, or a vibrant beachfront atmosphere, the Hamptons has something for everyone.

Where to Stay in the Hamptons (2025)

Gurney’s Montauk Resort & Seawater Spa (Montauk): Freshly renovated and absolutely stunning. Oceanfront views, a seawater pool, new restaurants (hello, Gigi’s), and a Dolce & Gabbana beach club. Worth the splurge.
Surf Lodge (Montauk): If you’re all about nightlife, Surf Lodge is the place to be. With a rotating lineup of DJs and artists throughout the summer, it’s the perfect spot to mingle and soak up the summer.
The Roundtree (Amagansett): Find peace at The Roundtree, a stylish boutique hotel in Amagansett. Featuring beautifully designed rooms and a cozy communal space, it’s perfect for relaxation during your Hamptons getaway.
Topping Rose House (Bridgehampton): Immerse yourself in historic charm at Topping Rose House. This hotel boasts elegant rooms, a local-favorite restaurant, and a stunning pool area making it a true gem in the Hamptons.
Marram (Montauk): A short walk from downtown Montauk, Marram is perfect for those seeking a quintessential East End experience. The hotel offers private surf lessons, fire pits for making s’mores, and an on-site restaurant serving delicious seasonal dishes.

3-Day Hamptons Itinerary

Day 1: Sag Harbor and Amagansett

Morning: Start your weekend with a scenic drive to Sag Harbor, grabbing coffee from Sagtown Coffee and donuts from Grindstone Coffee & Donuts. Take a stroll over to the waterfront and enjoy your coffee and donut while you take in the coastal harbor views. Afterward, explore more of the town shops or take a drive to the local beaches.

Lunch: Head to Amagansett for lunch at Bostwick’s. This spot is a personal favorite of ours, offering consistently delicious seafood classics like fried fish tacos, clam chowder, and hot buttered lobster rolls—it’s one of the best in the area!

Afternoon: After lunch, take a stroll through the streets of Amagansett and stop in some local shops and take in the charm of the town. Before you leave, make sure to take a drive over to Amber Waves Farm. Stock up on their jarred pasta sauces, farm-fresh produce, and seasonal baked treats.

Dinner: For dinner, choose between Sag Harbor Tavern or Duryea’s. At Duryea’s, you’ll enjoy incredible waterfront views, while Sag Harbor Tavern is known for its exceptional burger. You can’t go wrong with either choice!

Day 2: Montauk Beach + Nightlife

Morning: Begin your day with a coffee from Left Hand Coffee in Montauk. Then pack your beach essentials and head to Ditch Plains Beach for a relaxing morning by the ocean.

Lunch: Take a break from the sun and grab lunch at Gosman’s Dock, where you can enjoy endless oysters and drinks while watching fishing boats go through the harbor.

Afternoon: After lunch, take a scenic drive to explore other beaches or visit the iconic Montauk Lighthouse. The views from the top are stunning, especially during sunset. It’s one of our favorite things to do out east!

Dinner: End the day with dinner at Gigi’s located inside the Gurney’s Montauk Resort. After your meal, cozy up by one of the fire pits and enjoy the evening with a nightcap.

Day 3: Final Day in the Hamptons

Morning: Start your last day out east with pastries from the Montauk Bake Shoppe and coffee from Hampton Coffee Co. Take a short stroll up the street for one last morning at the beach before heading home.

Lunch: Don’t miss a visit to Round Swamp Farm to grab some of their famous prepared foods. Be sure to try the chicken fingers, tuna salad, fresh guacamole, and homemade granola—perfect snacks for the drive back. Or if you want a sit-down meal, stop at Sant Ambroeus in East Hampton. Can’t go wrong with some lunch, an iced cappuccino and a slice of the Principessa cake.

Afternoon: Wrap up your Hamptons weekend and swing by one of the local farm stands. Grab some fresh produce or prepared goodies to take back home. Personally, I never leave without a stop at Amber Waves Farm – it’s become a tradition for us on our drive home from the Hamptons.

Bonus Stop: As you make your way out of town, don’t miss Levain Bakery for some of the most incredible chocolate chip cookies you’ll ever taste. It’s the perfect sweet ending to your weekend in the Hamptons adventure!

Final Things to Know

Book everything in advance. Yes, even brunch.
Pack layers: Nights by the water can get breezy.
Support small: From Popup Bagels to farm stands, the best things out east aren’t always on Resy.

Frequently Asked Questions – Hamptons Weekend

What’s the best time to visit the Hamptons?

Late spring and early fall are ideal—fewer crowds, better hotel rates, and beautiful weather.

Can you do the Hamptons without a car?

Yes! You can take the LIRR or Hampton Jitney, then use Uber or rent bikes locally. Some towns are very walkable.

What town should I stay in for my first trip?

Montauk or East Hampton are great choices if you want the full experience—beaches, dining, and nightlife all nearby.

This Hamptons weekend guide is packed with everything you need to enjoy the best of what the Hamptons has to offer. Have an amazing trip and make the most of your getaway!