The Hamptons are a beloved getaway destination, offering a mix of stunning scenery, upscale shopping, and some of the best dining in the region. My recent weekend trip, which took place on November 1st, was a perfect blend of great food, picturesque towns, and a chance to relax and unwind in the crisp fall air. Here is a weekend travel guide to the Hamptons that showcases our culinary adventures. It highlights the best parts of our trip. This guide is perfect for anyone planning a trip to the Hamptons.
This is your weekend travel guide to the Hamptons to make the most out of your stay.
Day 1 – Friday
Arrival and Exploring Sag Harbor
We landed at JFK airport at 9:00 am, and after picking up our rental car, we set off on a scenic drive towards the Hamptons. The drive took us about 1.5 to 2 hours, depending on traffic, but the journey was well worth it as we arrived at Topping Rose House in Bridgehampton at 12:30 pm. This property was our home base for the weekend, offering a peaceful retreat to relax and enjoy the luxury of the area.
Lunch at Lulu’s & Exploring Sag Harbour
By 12:45 pm, we had lunch reservations at Lulu’s in Sag Harbor, a charming town known for its coastal beauty. Lulu’s did not disappoint. The food was fresh, flavorful, and the atmosphere was both lively and welcoming. We were able to enjoy delicious seafood dishes while soaking in the vibrant Sag Harbor vibe. It’s definitely a place I’d return to on future visits.
After lunch, we spent a little time shopping around Sag Harbor, browsing the boutiques and taking in the town’s quaint charm.
Exploring Southampton
By 4:30 pm, we drove over to Southampton, where we explored the shops and nearby restaurants.
Bobby Van’s Steakhouse
While Southampton has a great selection of places to visit, our evening ended with dinner at Bobby Van’s Steakhouse.
Unfortunately, Bobby Van’s didn’t quite live up to the hype. The steak was good, but nothing extraordinary, and the overall experience wasn’t as special as I had hoped. The service was fine, but I personally wouldn’t go out of my way to visit again.
Day 2 – Saturday
Breakfast at Jean-Georges
The next morning, we started the day with a fantastic breakfast at Jean-Georges at Topping Rose. Located within our hotel, this restaurant served a perfect breakfast spread, from fresh fruit to delicious eggs and pastries. The elegant setting was a great way to ease into a busy day of exploring.
Exploring Montauk
By 11:45 am, we headed out to the Montauk Point Lighthouse, one of the most iconic landmarks in the Hamptons. The lighthouse offers stunning views of the ocean and is a great place for photos. Fall in the Hamptons brings a unique charm. The season offers cooler temperatures and a quieter, more relaxed atmosphere than in the summer months. After taking in the scenic vistas, we entered Montauk Town around 1:47 pm. We wandered through the local shops. We enjoyed the town’s laid-back vibe.
At 2:00 pm, we stopped by Gurney’s Resort in Montauk, and I’m so glad we did. Known for its luxurious beachfront setting, Gurney’s is truly a standout property. The resort offers stunning ocean views and a beautiful private beach. It provides a collection of upscale amenities. This makes it a perfect destination for those seeking luxury in Montauk. Whether you’re enjoying a relaxing day by the water, Gurney’s meets expectations. You can also dine at one of their acclaimed restaurants. It’s definitely a spot I’d recommend if you’re looking for a high-end, relaxing getaway.
After enjoying the views and the peaceful atmosphere at Gurney’s, we made our way through Amagansett, NY at 3:00 pm.
Bostwick’s Chowder House & East Hampton
One of the day’s biggest highlights was our visit to Bostwick’s Chowder House in East Hampton. We arrived at 3:20 pm, and it was absolutely incredible. If you love fresh seafood, Bostwick’s is a must-visit. The casual yet welcoming atmosphere made it a great stop for lunch, and I’d definitely return the next time I’m in the area.
After lunch, we made our way to East Hampton, known for its upscale shopping. We visited the Ralph Lauren store. We enjoyed some retail therapy. Around 5:30 pm, we headed to Watermill, a residential area with stunning homes.
Saturday Evening – Dinner & Drinks
As the evening approached, we headed to Le Bilboquet in East Hampton for drinks at 8:00 pm. This French bistro has a reputation for being chic and trendy, but the atmosphere didn’t quite match my expectations.
At 8:30 pm, we moved on to Tutto Ilgiorno in Southampton for dinner. This Italian restaurant was a definite highlight of our trip. The food was exceptional, and the atmosphere was perfect for a leisurely dinner. The seafood pasta was a standout dish, and the homemade desserts were the perfect way to end a meal. If you plan on dining here, be sure to make a reservation in advance—it’s always busy.
Day 3 – Sunday
Departure and Reflections
On Sunday morning, we packed up and made our way back to JFK, already thinking about the next trip. If I could do this weekend over again, I’d probably add an extra night to my stay to explore even more of the area. There are so many hidden gems in the Hamptons, and I’d love to ride horses or visit a winery, both of which are popular activities in The Hamptons.
Our Favorite Towns
Throughout our weekend, we visited some beautiful towns that really stood out:
- Sag Harbor – With its charming shops and lively atmosphere, this town was a perfect place to spend the afternoon.
- East Hampton – Known for its upscale vibe and great shopping, East Hampton was a wonderful place to explore.
- Montauk – The relaxed, coastal vibe of Montauk was a perfect contrast to the more upscale areas in the Hamptons.
- Bridgehampton – Where we stayed at Topping Rose, this town offered a peaceful atmosphere with a touch of luxury.
- Southampton – With its mix of shopping, dining, and beautiful homes, Southampton was a lovely spot to visit.
If you’re planning a fall trip, this weekend travel guide to the Hamptons offers a perfect mix of food, shopping, and scenic relaxation. You might seek upscale dining, quaint towns, or stunning coastal views. The Hamptons in fall offers a unique, quieter experience. It’s definitely worth the visit.
