Your Guide to a Weekend in the Hamptons

Planning a weekend getaway to the Hamptons, NY? This guide covers everything you need to know about this iconic destination, including the best places to stay, top beaches to visit, and must-try restaurants. Check out my comprehensive Hamptons weekend guide and plan your next trip out east this summer!

Where Are the Hamptons?

Situated on Long Island’s South Fork, the Hamptons encompass several charming towns, including East Hampton, Southampton, West Hampton, and Bridgehampton. Each offers its own unique blend of luxury and relaxation, making it the perfect destination for a weekend escape.

NYC TO THE HAMPTONS

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 a quick rundown by mode of transportation:

By Car: For maximum flexibility, driving a car is the way to go. Hop on the Long Island Expressway (I-495), take exit 70, and follow the signs for 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: Opting for a weekday escape (Monday to Thursday) typically means smoother traffic and better chances for snagging accommodations and restaurant reservations. If you’re in the mood for a more laid-back journey, the Long Island Rail Road (LIRR) offers direct service from Penn Station to various Hamptons spots. The trip usually clocks in at around 2-3 hours. You can hop off and on at stops like East Hampton, Southampton, and Montauk.

By Bus: Looking for convenience and affordability? Several bus services link NYC to the Hamptons, providing a fuss-free option. Depending on traffic, the journey typically takes anywhere from 2.5 to 4 hours.

Best Times to Travel to 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.

Off-Peak Season: 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

Southampton: Experience coastal town vibes with luxurious shops and eateries. Perfect for boutique shopping, trendy cafes, and beach relaxation.

Bridgehampton: A blend of farm stands and high-end boutiques. Enjoy fresh local produce and upscale shopping.

East Hampton: Home to stylish boutiques and art galleries. Explore chic shops and a vibrant art scene.

Amagansett: Known for chill beaches and local eats. Relax on beautiful beaches and discover local dining and boutiques.

Sag Harbor: Offers historic charm with an artsy twist. Stroll through downtown, explore galleries, and enjoy the creative atmosphere.

Montauk: Famous for laid-back luxury and endless beaches. Enjoy relaxed beach days, upscale accommodations, and lively nightlife.

Westhampton Beach: Ideal for family-friendly fun and relaxation. Main Street features charming shops and restaurants.

Water Mill: Known for its historic water mill and scenic landscapes. A haven for nature lovers and artists, with beautiful gardens and serene ponds to explore.

WHERE TO EAT

When it comes to dining in the Hamptons, there’s no shortage of coastal spots to indulge in. Here are some must-visit restaurants in the Hamptons to elevate your weekend getaway:

• Duryea’s Lobster Deck (Montauk): Begin your Hamptons adventure at Duryea’s Lobster Deck. This iconic spot serves the freshest seafood with stunning coastal views.
• Sen (Sag Harbor): A local favorite for upscale sushi in downtown Sag harbor.
• Sag Harbor Tavern (Sag Harbor): If you are looking for a classic burger or incredible grilled branzino, look no further than Sag Harbor Tavern. They are open Friday-Saturday, kid-friendly, and the perfect spot for a casual dinner.
• Wölffer Kitchen (Amagansett): This restaurant offers a menu inspired by local ingredients and pairs perfectly with wines from the renowned Wölffer Estate Vineyard.
• Popup Bagels at the Meeting House (Amagansett): If you haven’t tried these small batch bagels in the city already, this is your sign. Located at the newly reopened Meeting House, place an order here and start your summer mornings with some of the best bagels and delicious schmears.
• Almond (Bridgehampton): Almond offers a charming bistro experience with a menu showcasing fresh, seasonal ingredients. A beloved spot for locals and visitors.
• Scarpetta Beach (Montauk): Located at Gurney’s Montauk Resort, enjoy Italian-inspired cuisine with modern twists and oceanfront views. Be sure to order the signature spaghetti.
• The 1770 House (East Hampton): Step into history at The 1770 House, an East Hampton icon with a menu celebrating seasonal and local fare.
• Placebo (Montauk): A vibrant new addition to Montauk, bursting with Latin flavors and transforming into a high-energy dinner party with guest DJs after 9 PM. For a more intimate cocktail experience, Don Jaguar’s is an exclusive speakeasy lounge, accessible only by invitation or by inquiry at askthedon@elgruposn.com.
• Navy Beach (Montauk): For a quintessential beachfront dining experience, head to Navy Beach on the sands of Fort Pond Bay. The relaxed atmosphere and coastal eats are a must.
• Bostwick’s (East Hampton): My favorite restaurant out east has to be Bostwick’s. It’s known for its casual, nautical atmosphere, and has some of the best seafood in the Hamptons. Be sure to order the fried fish tacos, buttered lobster roll, shrimp cocktail and the coconut shrimp spring rolls.
• Ocean Club Montauk: A new 2024 summer restaurant at the Montauk Yacht Club on Star Island, featuring a seafood-forward menu and extensive raw bar.
• Surf Lodge (Montauk): Not just a place to stay, Surf Lodge has a restaurant with incredible sunset views. It’s a prime spot for mingling, live music, and soaking in the Montauk scene.
• Gosman’s Dock (Montauk): As a staple seafood destination in Montauk, Gosman’s Dock is renowned for its fresh seafood and refreshing drinks served in a laid-back coastal atmosphere.

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

• Gurney’s Montauk Resort & Seawater Spa (Montauk): Experience incredible oceanfront views at Gurney’s Montauk Resort & Seawater Spa. Perched on Montauk’s cliffs, this resort offers a spa, beach club, and multiple dining options.
• 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.

Weekend in the Hamptons: A Perfect 3-Day Itinerary

Day 1: Explore Sag Harbor and Amagansett

Morning:  Start your day with a drive to Sag Harbor for a cup of coffee from Sagtown Coffee and donuts from Grindstone Coffee & Donuts. Take a walk to the walk to the waterfront to enjoy your coffee and donut as you take in the coastal views. After you are done with your coffee, take a drive around the villages or hit up 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 buttered lobster rolls—it’s hands down one of the best in the area!

Afternoon: After lunch, take a stroll through the streets of Amagansett. Be sure to 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: Treat yourself to a memorable last-night dinner at either Sag Harbor Tavern or Duryea’s. Duryea’s offers amazing views if you can snag a table, while Sag Harbor tavern has an incredible burger. You can’t go wrong with either spots.

Day 2: Beach Day in Montauk

Morning: Kickstart your day with a coffee from Left Hand Coffee in Montauk. Don’t forget to pack up your beach essentials before heading to Ditch Plains Beach for a day of fun in the sun.

Lunch: After your beach day, take a drive to Gosman’s for lunch. Here you can enjoy endless oysters and drinks while watching the fishing boats go through the harbor.

Afternoon: If you’re up for it, take a scenic drive to explore other beaches, or better yet, make your way to 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: Wrap up your day with dinner at Scarpetta Beach located in the Gurney’s hotel. After your meal, head over to Gurney’s to hang out by one of the fire pits and enjoy the relaxed ambiance.

Day 3: Final Day in the Hamptons

Morning: To start your last day out east, stop at the Montauk Bake Shoppe for some pastries for the drive home. Be sure to grab a coffee at Hampton Coffee Co and take one last walk over to the beach.

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 – it’s become a tradition for us on our drive home from the Hamptons New York.

Bonus Stop: As you make your way out of town, don’t forget to swing by 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!

This comprehensive hamptons weekend guide is designed to give you a taste of everything the Hamptons offers. Enjoy your trip and make the most of your weekend getaway!