top of page

Indulge In Luxury: A Weekend Getaway To The Hamptons

Updated: Dec 18, 2023

My stay at the Roundtree Amagansett was compensated. My views and opinion of the location and accommodation are authentically my own.

Greetings from The Hamptons! I’m thrilled to be here and take you along with me on my first-time visit.

I’ll be spending the weekend in Amagansett, located in East Hampton, just a quick 2.5-hour drive from New York City.

The East Hampton area includes Sag Harbor, East Hampton village, Amagansett, and Montauk, among others, offering plenty of beautiful beaches, restaurants ranging from casual to upscale, art galleries, social clubs, and lots of boutiques to explore. Let’s go!

As a first-time visitor, I recently stayed for the weekend at The Roundtree Amagansett, a charming boutique hotel in the heart of Amagansett village, and it did not disappoint.

From the comfortable and stylish accommodations to the convenient location and the endless things to see and do nearby, The Hamptons and The Roundtree Amagansett truly exceeded my expectations.

Best Transportation Options to the Hamptons from NYC

The Hamptons is a popular weekend destination for New Yorkers looking to escape the city. There are various transportation options available to get to the Hamptons from New York City.

One can take the train, bus, drive, or hire a private car service.

Each option has its advantages and disadvantages in terms of cost, convenience, and time.

It’s important to consider these factors when deciding which transportation option is best for your needs.

Once you’re in town! Here’s how to get around.

If you don’t have a car in the Hamptons, don’t worry! Local transportation options include ride-sharing services like Uber and traditional taxi companies such as Lindy’s and Carlos Taxi.

For a fun and eco-friendly option, check out The Free Ride’s electric shuttle, which offers free rides between East Hampton town and Main Beach.

If you prefer to explore on two wheels, Bermuda Bikes in East Hampton offers rentals starting at $35 for an 8-hour day, and Amagansett Beach and Bicycle Company offers tandems and kid’s cruisers starting at $19 per hour and $39 per day.

However, driving is the most convenient way to get around the Hamptons, especially if you want to explore different towns and beaches. It’s worth noting that parking can be difficult to find during peak season, so it’s a good idea to plan ahead and be prepared to walk a bit if necessary.

The Roundtree Amagansett: A Charming Retreat in the Hamptons

The Roundtree Amagansett is a luxury boutique hotel located in the town of Amagansett in the Hamptons, New York.

This charming property is housed in a restored 19th-century house and features 15 beautifully appointed guest rooms and suites with a mix of traditional and modern decor.

The hotel boasts a tranquil outdoor pool and gardens, a cozy library with a fireplace, and a restaurant serving seasonal farm-to-table cuisine.

The Roundtree Amagansett is a perfect spot for a relaxing Hamptons getaway with its serene atmosphere and top-notch amenities.

Checking Into The Hotel

The hotel’s check-in time is at 4:00 PM while check-out time is at 11:00 AM. To secure your room(s), a 100% deposit of the room rate plus taxes will be charged upon booking.

The hotel is pet-friendly and offers dog beds, water bowls, and welcome treats for a fee of $50 per night per pet. Smoking is strictly prohibited in all rooms, cottages, and public spaces.

Complimentary on-site parking and daily continental breakfast are available for all guests.

The hotel provides beach cruisers for guests to access the nearby Atlantic Avenue Beach, which is about a mile away.

As the sun began to set, I made my way to the fire pit to unwind and warm up. The guest services team even provided a s’mores kit, which I thought was such a thoughtful touch!

During my stay, I was fortunate enough to experience their recently updated standard guest room, which boasted lavish decor, a contemporary bathroom with a European vanity and a walk-in shower, a customized queen bed, and Matouk towels, which quickly became my latest fixation.

Breakfast is delivered to your room each morning as a guest. When you check in they ask you to complete a survey to share your preferences and any allergies you may have.

Amagansett Experiences

If you’re new to the Hamptons, why not explore the town in different ways? The Amagansett Experiences are a great option for travelers visiting the area. The Signature Experiences are thoughtfully curated based on your interests, from winery tours to day-long excursions. Simply inquire with the reservations team when booking your stay and they will coordinate everything for you through Guest Services at an additional cost prior to your arrival.

For those seeking a “work-cation,” the Roundtree team has got you covered! They offer a perfect setup to work remotely while feeling at home, including 15% off the nightly rate with a 3-night minimum stay, complimentary laundry service, and a standing desk setup upon request. This is the perfect solution for all the digital nomads and remote workers out there!

Places to Dine Around Amagansett

Amagansett has plenty of dining options that offer various cuisine options. Here are some popular dining spots in the area:

  1. The Lobster Roll: A classic seafood shack that has been in the area since the 1960s. They offer lobster, shrimp, clam chowder, and other seafood dishes.

  2. The Palm: A classic steakhouse that is known for its prime cuts of beef, seafood dishes, and excellent service.

  3. La Fondita: A casual Mexican eatery that serves authentic Mexican street food such as tacos, quesadillas, and tamales.

  4. Bostwick’s Chowder House: A seafood-focused restaurant that offers fresh seafood dishes such as clam chowder, lobster, and crab cakes.

  5. Coche Comedor: A modern Mexican restaurant that serves creative dishes such as duck mole tacos and ceviche.

@ wolfferkitchen

Some personal favorites I enjoyed include:

  1. Wolffer Kitchen Amagansett: Located in the heart of Amagansett, Wolffer Kitchen Amagansett is a popular restaurant and wine stand known for its delicious food and great ambiance. The menu features seasonal dishes made from locally sourced ingredients, with a focus on seafood, pasta, and small plates. In addition to the food, Wolffer Kitchen Amagansett offers an extensive wine list, featuring wines from the nearby Wolffer Estate Vineyard.

  2. Cove Hollow Tavern: A local favorite, Cove Hollow Tavern is a gastropub that serves American comfort food with a sophisticated twist. The menu features classics like burgers and steak, as well as unique dishes like roasted duck and pan-seared scallops. Cove Hollow Tavern also offers an extensive selection of wine, beer, and cocktails.

  3. Tutto Il Giorno: Tutto Il Giorno is a trendy Italian restaurant in Sag Harbor, just a short drive from Amagansett. The menu features traditional Italian dishes made with fresh, seasonal ingredients, such as homemade pasta, wood-fired pizza, and grilled meats and seafood. Tutto Il Giorno also has an impressive wine list, featuring both local and Italian wines.

  4. Il Buco Al Mare: Il Buco Al Mare is a Mediterranean-inspired restaurant located in Amagansett. The menu features fresh seafood, homemade pasta, and other seasonal dishes, with a focus on local, sustainable ingredients. The restaurant has a relaxed, beachy vibe, with a beautiful outdoor patio overlooking the ocean. Il Buco Al Mare also offers an extensive wine list, with a focus on natural and biodynamic wines.

There are many more options, ranging from farm-to-table eateries to casual cafes. Visitors will have no trouble finding a restaurant that suits their taste and budget.

Places to Shop Around The Town

LVIS Bargain Box Thrift Shop: This is a local gem! I had the thrift shop on my list while doing pre-trip research and loved shopping and supporting! They have high quality brands like Vineyard Vines, Lilly Pulitzer, Ralph Lauren, I even found Dolce and Gabbana items in the shop at a shockingly affordable prices. Most of the items are donated and all sales benefit The Ladies’ Village Improvement Society of East Hampton.

Shack Fancy in Sag Harbor is literally the cutest, while fashion filled with embroidery and lace. What’s not to love?

Amagansett Square with everything from Love Adorned to Jenni Kayne! Amagansett square is the perfect spot to visit. They have everything you need in one place to shop, dine, and more!

Nightlife Around the City


Social Club and Surf Lodge are two popular nightlife spots around Amagansett.

The Social Club is a lively restaurant and bar that offers cocktails and small plates in a relaxed atmosphere. It also has a back patio for outdoor seating.

The Surf Lodge is a waterfront hotel, restaurant, and bar that is known for its live music and events. It is a popular spot for both locals and tourists and offers a great view of the sunset over the water. The Surf Lodge also has an outdoor area where guests can relax on the beach or around a bonfire.

There are several other options for grabbing a drink, including the Stephen Talkhouse, a popular music venue that hosts live performances by local and national acts.

For a more upscale experience, visitors can head to the Living Room at the Maidstone, which offers a cozy fireplace and a wide selection of wines and cocktails.

Additionally, the Montauk Brewing Company, located just a short drive away in Montauk, offers a variety of local beers that visitors can sample in their tasting room.

Final thoughts

Amagansett, The Hamptons was phenomenal. The area boasts of stunning Victorian style homes, beautiful beaches, and friendly locals. I indulged in shopping and dining, which added to the overall enjoyment of my stay.

Have Your Trip To The Hamptons Planned By A Professional!

Experience all that The Hamptons has to offer with a custom itinerary tailor made for you.


bottom of page