A guide to The Hamptons – where to stay, where to eat and things to do

This post was originally written on June 2019 and features things to do in the Hamptons, mostly in Montauk, and it was updated in July 2020 with tips of our second time in Montauk

I think the Hamptons are in the imagination of a lot of people, perhaps not in the same proportion as New York City, but the area has also been featured on a lot of movies and TV series – like Gossip Girl, Revenge, Sex and the City and The Affair. I had already been to Southampton three years ago but I’ve always wanted to explore more. Finally, we set some time to spend a longer period there and enjoy more that the area has to offer! In today’s post, I share these tips with you. I hope you enjoy it – I love exploring places near New York and bringing this to you. I think a lot of people have few references in the area – trust me: it is more than luxurious houses. You can find a lot of nature and spots for breathtaking sunsets.

Understanding the Hamptons

I think it’s worth giving a sense of location and geography to you, first of all. The Hamptons, part of the East End of Long Island, comprise a group of villages in the cities of Southampton, East Hampton and Montauk. Look at the map below, with the three cities marked. This entire area around them has several villages, and all of these forms the Hamptons. The region is famous in the summer – it is the high season – but the truth is that the Hamptons have become increasingly a year-round destination for New Yorkers seeking refuge on weekends. Curiosities: the prices of residential properties in the Hamptons are among the highest in the US and private golf clubs in Southampton are among the most exclusive and expensive in the country.

Where to stay

Considering that the Hamptons are a huge area, there are several lodging options. You can search for hotels – you will find from the most complete, beachfront, with resort structure, to the simplest ones. Another good idea is to use Airbnb – the offer of houses and apartments is high throughout the area – and prices drop a lot during the fall/winter. Believe it: The Hamptons go beyond the beaches and can be an excellent option off the tourist route for travelers to New York City – or for those who live in the area.

Our hotel – Ocean Colony Beach & Tennis Club

We stayed at a hotel in Amagansett, a village located between East Hampton and Montauk. It is a beachfront resort, and the rooms, in fact, are mini-apartments, with amazing structure: bedroom with TV, super spacious closet, bathroom, living room and fully equipped kitchen (coffee maker, toaster, dishwasher, microwave, and oven), huge balcony. We were very pleased with the hotel, it was far beyond our expectations. It has free parking and easy access to the beach, with chairs, umbrellas and towels included. In addition, the hotel has a swimming pool and a tennis court. There is no breakfast – but this was not a problem with the structure we had. We bought food at a market in Montauk and had coffee in the room itself.

We booked the hotel through HotelTonight app – Use the code LPERUCHIMEZARI and get $ 25 OFF on your first reservation through HotelTonight.

For anyone planning to explore the Hamptons, I suggest planning a script of what interests you and then looking for a place to stay that is halfway there. Overall, the distances from the places that I will suggest in today’s post are 15-20 minutes driving from one point to another on average.


We rented a car as we stayed two nights in the area and honestly, it would be very complicated to explore the area without a car. It took us 2h40min driving from Manhattan to our hotel. The car gives you much more freedom and flexibility to explore everything. Speaking of renting in New York, getting the car off Manhattan is cheaper – usually, airports have the best fares. Another option is to use public transportation to one of the cities of the Hamptons and from there pick up a Uber/Taxi to the rental car. There are some rental companies in the area.

Another idea is also to hire a private tour with a transportation company. Leco Tour offers this one-day tour around the area to check out some cool spots in the area. The company has super comfortable cars, so you can explore the Hamptons without worrying about anything else. It is a private tour, the car can fit up to 6 people and the route passes through the famous mansions, main street, wineries. Do not forget to mention that you are a blog reader to ensure a special discount.

  • Leco Tour Transportation – + 1 917-293-4754 – / 

You also have a public transportation option, but I do not consider it to be so advantageous. Explain: you use the train to get to the towns, but then you need a car to go from one point to another. Yes, there are taxi companies and even Uber, but for the first option you need to call and request a car and for the second the service does not work as fast as in the city for example. There are trains running from Penn Station – Long Island Railroad LIRR. Clicking here, you can check the map. See the Montauk Branch line, at the end of Long Island. Note that the train has stops in Southampton, Bridgehampton, East Hampton, Amagansett, and Montauk. To give you an idea, departing from Penn Station, the path to Montauk lasts about 3h40 min by train. The amount of the ticket varies from  $20 to $30, depending on the time and day. You can click here and simulate the prices, check times, and duration of the trip – just choose PennStation origin and the desired destination (one of the stations I quoted above).

In addition, there are bus companies that make the journey, with several departing points in Manhattan and several stops along the Hamptons. You can click here and check the details.


The Restaurant at Baron’s Cove – our trip began with lunch at the Baron’s Cove restaurant, a hotel/resort in Sag Harbor, a region that also belongs to the Hamptons. The restaurant is super charming and has a beautiful view. The vast majority of restaurants in the Hamptons obviously have a focus on seafood (but there are other options, of course). This restaurant opens for lunch, dinner, and brunch and was very empty when we arrived. The food is a bit pricey, but the experience was worth it, the place is a delight for a summer day. We had oysters (half a dozen, $17), Fish Tacos (with two HUGE tacos, $ 25) and Fish & Chips (very generous portion, $ 25). The food was tasty, but nothing extraordinary. As I mentioned, it was worth the whole experience.

The Surf Lodge – It’s one of the most famous spots in Montauk and, guess what? It was founded by a Brazilian, Jayma Cardoso. When it opened in 2008, she intended to create a space that was true to the simplicity and beauty of Montauk – to remind her of Brazil. It is a boutique hotel, but even if you do not stay, you can enjoy the vibe of the place at the restaurant or at the bar. For you to have an idea, the Obama family has already stayed there, as well as supermodels and pop stars. Another cool thing is that from June to September they promote a series of cool concerts. Tip: the nearest parking is located at the train station, then you walk for about 5 minutes. The hotel’s parking is for guests only. Here, we order a drink and a beer (drinks cost $16, beers cost $7). You can check the menu by clicking here.

  • Open all year.



Navy Beach – this was the best restaurant of our trip and it was probably there that I saw (one of) the most beautiful sunsets of my life! Founded in 2010, Navy Beach quickly became the favorite seaside restaurant in Montauk. It has a private beach overlooking Fort Pond Bay and is a good spot for weddings. In addition to the seafood menu, it has one of the largest selections of rosé wines in the Hamptons. It has an incredible sunset and was voted by Newsday one of the top five ocean view restaurants in the East End. You can either get a table outside or inside. The menu is seafood-based and features small plates ($17), great for sharing. We ordered 5 of these (Tuna Tostada, Mussels, Octopus, Crab Cake, and Burrata). Also, I need to make an honorable mention of the Key Lime Pie, made at the restaurant. It was simply the best we have ever had! You can check out the full menu here. Even if you do not want to dine, do yourself a favor and go there for a drink and watch the sunset. It’s simply fantastic!

  • Open from April to September

Inlet Seafood Restaurant –another restaurant with incredible views, very crowded at sunset time. The menu is also focused on seafood, however, honestly, I opted not to include the photos of the dishes because we did not enjoy the food. We had baked oysters, grilled whole fish, and sushi. They were not bad, but they were not worth the price we paid. Here, I recommend going to have a drink and enjoy the sunset, because the view is very beautiful and worth it!

  • Open from February to November.

Bostwick’s Chowder House – this is a good choice of a seafood restaurant in East Hampton. It’s cute, it has an outdoor and indoor space and it gets very busy at the weekend. It probably has the most extensive menu out of all the restaurants we went to. Includes dishes with lobsters, oysters, shrimp, and other seafood. We had the classic Clam Chowder soup ($8) and also Fish Tacos ($24, HUGE, filled with guacamole too), and Crab Sandwich, with fries. I loved the food! Everything was very delicious and we were very satisfied!

  • Open from April to November.

The Montauket – this is a favorite spot in Montauk for a beautiful sunset. It is a bar, a restaurant and a hotel which was established in the 20’s and family-owned since 1959 and is known by locals as “the hill” because of the location. The menu features lobster rolls and fresh locally caught seafood besides local beers and special drinks. The place is very casual, the food is delicious – I had the scallops and they were so good – and the view is just perfect. Make sure to arrive before your intended time, since they don’t take reservations. Plus, they are open from Thursday to Monday.

A special tip: when we arrive, we had to put our names on the list and wait for 45 minutes, so we went to a walk towards the west through Fleming road and we found this hidden spot with the chairs. Is beautiful!

Clam Bar – another traditional spot in the Hamptons, is on the road, on your way to Montauk – it is actually in front of the resort where we stayed. This place opened more than thirty years ago and features, of course, a seafood menu. The highlight here is the lobster roll, a must-have, and also the sea salt caramel cheesecake.

Scarpetta Beach – this restaurant is in Manhattan as well and it is located at Gurney’s Montauk, a huge and beautiful resort in front of the ocean. It is a perfect spot for a romantic dinner or special occasion. It is so beautiful!  Open nightly year-round, this Italian hotspot features classics as well as seasonal dishes, fresh seafood selections, and a world-class wine list. From the 148-seat dining room, French doors open onto an outdoor deck, which seats another 106, every table has a panoramic view of the ocean.

Gosman’s Dock – this place is so cute! It reminds me of San Francisco in some way. You will find some stores, an ice cream place, and some restaurants here, plus a small event area and a fish market. We bought some beers and fish and chips from Gosman’s Clam Bar and got a table with a view to sitting. Just be aware of the seagulls, lol.

Places to visit

Sunset Beach – you can walk from Gosman’s Dock to this beach to watch the sunset. It is magical, I think I don’t need to say a lot of things, just look at the pictures and you will understand why.

Main Street East Hampton – those who go to the Hamptons and love the TV series need to include a visit to East Hampton (or Southampton) in the script. Basically, the idea is to walk down Main Street and enjoy the cute architecture of the shops, cafes, and restaurants. Another thing you should do is driving from Main Street to Main Beach. The path is simply fantastic, with tree-lined streets and you see the famous mansions behind their vegetation walls. Main Beach has parking and a nice structure, considering that most of the beaches are quite desert.

Wölffer Estate Vineyardone of the things I was most anxious about on this trip was to visit the wineries in the area! Unfortunately, we only had time to visit one – but it was well worth it! The Wölffer Estate Vineyard was founded in 1988 by Christian Wölffer, a man with a great creative vision and a huge passion for life. The property today belongs to and is operated by its sons, Marc and Joey Wölffer and Winemaker / Partner Roman Roth. The estate spans approximately 470 acres including the acclaimed 55 acres sustainably-farmed estate vineyard located in Sagaponack, NY, 52 acres on the North Fork of Long Island, 200 acres in Mendoza, Argentina, 2.5 acres in Mallorca, Spain and 160 acres managed in collaboration with North Fork growers. At the winery, you can obviously buy wines and also drink. The tasting with four varieties costs $25, but they also offer glasses, bottles and cheese boards.

  • Open all year
  • Check more recommendations on the map

Bike rental – Montauk is a great place to explore on a bike – in fact, you will probably see a lot of cyclists there! You can rent a bike at Plaza Surf and Sports – everything is thourgh an app, so make sure to download the Movatic app to unlock the bike and pay for the ride ($13 per hour). We went all the way to the Liar’s Saloon area though the S Essex St and the path was so beautiful and relaxing! Montauk Cycle Company also offers bike rentals. 

Camp Hero State Park / Montauk Lighthouse – I was in love with this place! We got there because the idea was to see the Montauk Lighthouse – but the park itself surprised me a lot more. To get there, put in the GPS Camp Hero Parking. Arriving at the parking lot, you will already come across incredible views of the sea, with beautiful cliffs, an immensity of water and a charming silence. Seriously, what a place! The light of the end of the day leaves everything much more beautiful. We walk along the trail until you see the lighthouse – it’s a favorite spot for weddings. Then we took the car and drove to the parking lot of the lighthouse, took a side path, and arrived at a beautiful beach. There’s also the Georges Lighthouse Cafe in the area for a drink or a snack. Parking costs $8, but it’s free after 4PM. You can also enter the lighthouse – the ticket costs $12. But, you have to be aware of the times on the official website.

Turtle Cove – when you arrive at the Montauk Lighthouse, check the trail maps in the area, follow the path and go to the other side of the Lighthouse – you will arrive at Turtle Cove, a famous beach for surfing and fishing. It is so calm and beautiful! If you watch The Affair, you will remember some scenes!

LongHouse Reserve  – LongHouse Reserve is a 16-acre reserve and sculpture garden located in East Hampton featuring pieces from Buckminster Fuller, Yoko Ono and Willem de Kooning to name a few. LongHouse Reserve was founded by Jack Lenor Larsen, internationally known textile designer, author, and collector.  His home, LongHouse, was built as a case study to exemplify a creative approach to contemporary life. He believes visitors experiencing art in living spaces have a unique learning experience – more meaningful than the best media. LongHouse contains 13,000 square feet and 18 spaces on four levels. The gardens present the designed landscape as an art form and offer a diversity of sites for the sculpture installations. I was delighted with this place – and it reminded me of a lot of Storm King, but in a smaller proportion. The place is charming and I’m glad we got to know it!

  • It is open on Wednesdays and Saturdays, from April to November, tickets are $15.

Honestly, Montauk won a place in my heart. It has many natural beauties, a beach town vibe, simple atmosphere. I loved it and really want to go back!

Did you like my tips? Always remember to check Google’s opening hours. All the places mentioned in the post are marked on the map, which includes other suggestions of places that we couldn’t check!

Please be free to recommend more places in The Hamptons!

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