The 9 Essential Things to Do in The Hamptons in Summer

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The quintessential factor that makes the Hamptons such a great choice to spend the summer is the sheer range of activities and experiences to keep you happy and occupied. There are things to do in the Hamptons for all types of traveler, whether you want beach and relaxation time in Amagansett, a party like no other at Montauk, high-end shopping in East Hampton, or even a deep dive into whaling history in Sag Harbor.

The guiding principle of this list is to curate the best of what the Hamptons has to offer in every category. We haven’t covered every single thing to do in the Hamptons; rather, we’ve covered everything on the spectrum of experiences on offer so you can taste the best of the Hamptons lifestyle. One thing we can say is to make sure you carve out plenty of time to soak in the beauty, vibes and tastes of the region: nobody leaves the Hamptons disappointed.

When is the best time to visit the Hamptons in summer?

The Hamptons is undoubtedly one of the premier summer destinations for New Yorkers and East Coasters generally, and that usually means virtually every area in the Hamptons will be brimming with visitors during the high summer months of June, July and August. While high summer is absolutely a great time to visit the Hamptons, September and October offer perfectly crisp summer-like weather (which, in our opinion, is much more bearable) with fewer visitors.

Fewer visitors is another way of saying you’ll have a much easier time getting a reservation at the delicious restaurants in the Hamptons (and particularly the best restaurants in Sag Harbor). Peak summer is a busy almost everywhere all the time (especially on the weekends), so you’ll want to make sure you’re prepared with advance bookings for everything from your rental car to your accommodation to your dinner and lunch reservations.

The Hamptons in winter

And for those of you thinking about a trip to the Hamptons during winter, you should know that it is absolutely a great idea. Restaurants and establishments generally in the Hamptons are built for both seasons, so expect cozy vibes in the winter.

Getting around the Hamptons

The short answer is you absolutely need to rent a car for your time in the Hamptons. There are other excellent East Coast vacation spots where you don’t need a car like Nantucket, but restaurants and activities in the Hamptons are spread out throughout the region. Unless you’re going to stay in one spot in the Hamptons or can justify high taxi prices, make sure to book your rental car in advance.

Rent a car for the Hamptons at one of the major New York-area airports like JFK or LGA, or if you prefer to rent a car closer to the Hamptons rather than battle the traffic into the Hamptons, East Hampton Airport and Islip Airport both have car rental options available – but they tend to get booked up during summer so book early.

Getting to the Hamptons

It’s a flat out lie to say that there is public transport to get you around the Hamptons with ease, but there is certainly public transport to get you to the Hamptons.

Bus

The most comfortable way of getting to the Hamptons is take the Hampton Jitney bus or Hampton Ambassador bus. Both of these luxury liners make stops throughout the Hamptons which includes all of the major towns, but you may very well need to get a taxi or use a rideshare app like Uber for your last mile.

Train

The other option is to take the train from Penn Station in New York City to your stop in the Hamptons. The train line runs all the way through to Montauk, and the best part is that you don’t have to stew in traffic for hours. It’s quite a comfortable journey, and we’re glad to say that it’s actually quite reliable in terms of schedules (which is more than we can say for most American train lines).

Helicopter / Seaplane

Arriving by helicopter or seaplane into the Hamptons is certainly the most flashy mode of transport, though we accept it is absolutely not the most economical choice. The premier provider of helicopter services between New York City and the Hamptons is BLADE which can get you from city to beach in less than half an hour.

But where you make in time, you’ll pay in cash: seats usually run upwards of US$1,000 per person. Having said that, it’s also an experience in and of itself to fly into the Hamptons by helicopter. There is also something to be said about not having been through the stress of upwards of six hours of gridlock traffic upon your arrival to the Hamptons.

The Curated List of the Essential Things to Do in the Hamptons

1. Enjoy the wines at Wölffer Estate

Wölffer Estate Vineyard is one of very few wineries in the Hamptons and is easily among the best of the wineries on Long Island. Some of the best varietals of the region can be tasted at Wölffer which wouldn’t be out of place in the Napa with its sheer variety of options. Spending an afternoon walking through the vineyard and sampling wines is undoubtedly one of the quintessential things to do in the Hamptons.

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If you’re looking for the best wineries on Long Island generally, you’ll notice that virtually all of the wineries are located on the North Fork which is north of Peconic Bay.

2. Go surfing and/or fishing in Montauk

If you’re into surfing, chances are that you’ve already heard of Ditch Plains which is almost a byword for surfing among Hamptons locals and frequent visitors. And even if you’re not into surfing, there is excellent people watching. There are plenty of other beaches in Montauk, but there is no better than Ditch Plains if you’re looking for the best surf.

Montauk is also an excellent place to go fishing. If it’s your thing, charter a fishing boat and enjoy some of the best fishing on offer in the region. In fact, Montauk is known locally for having some of the best fishing in New York State. If you do charter a boat, you should expect to leave early in the morning.

3. Laze on one of the best beaches on the East Coast

You’re spoiled for choice in the Hamptons for beaches. But no matter where you pick, there is absolutely no doubt that one of the essential things to do in the Hamptons is to spend a day on the beach. One of our favorites is Atlantic Beach in Amagansett which boasts white sand and gorgeous sand dunes. And yes, you can get ice cream a Atlantic Beach.

One of our other top picks is Main Beach in East Hampton which is complete with a snack bar on the beach. A beach day in East Hampton also by necessity includes a walk along the main street in East Hampton which is replete with high-end brands from Gucci to Brunello Cucinelli.

4. Get a Lobster Roll (preferably from LUNCH)

There is no food more emblematic of the northwest of the United States than the not-so-humble lobster roll. And in the Hamptons, you can fully expect to have some of the best lobster rolls on offer. Restaurants and takeaways in the Hamptons are in covert competition with each other to produce the best lobster rolls – so much so that we’ve written a separate post on the best lobster rolls in the Hamptons.

In our view – and, we would guess, in the view of most Hamptonians (is that the correct demonym?) – one can’t say they have visited with the Hamptons without eating a lobster roll in the sunshine. Lobster rolls in the Hamptons are like baguettes to Paris – maybe not quite, but still, you’ll be guaranteed a fresh and super tasty lobster roll at most places in the Hamptons.

LUNCH has been serving up some of the best lobster rolls in the Hamptons for quite literally half a century, so you know you’re going to get the best of the best. They also make their lobster rolls in a variety of ways so there’s usually something to satisfy even the pickiest eater.

5. Have lunch at Sunset Beach Hotel on Shelter Island

You wouldn’t be judged for mistaking Sunset Beach Hotel, a boutique hotel on shelter island, for a classy restaurant in the south of France. The setting is absolutely stunning, but it doesn’t stop there: the team at Sunset Beach know exactly how to create the quintessential Hamptons experience that we see in the movies. It’s exclusive, cool and just generally a great place to spend an afternoon.

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There are so many other fantastic options for lunch on the water in the Hamptons that it can be hard to say that Sunset Beach Hotel is the best of them. If you’re looking for other options, you absolutely cannot go wrong with Si Si in the Springs part of East Hampton, or Duryea’s in Montauk (get the lobster roll).

6. Visit the Montauk Point Lighthouse Museum

Montauk Lighthouse is the oldest lighthouse in New York State and was designated a National Historic Landmark over ten years ago. It’s become a symbol of the Hamptons or at least Montauk, and it’s a surprisingly relaxing place to talk a walk through in the afternoon. And if you need further incentive, very occasionally you can spot whales from the lighthouse.

7. Take the sunset cruise on the American Beauty II

Getting out on the water is an essential part of any trip to the Hamptons, and the best way to do so is on a sunset (cocktail) cruise aboard the American Beauty II which sets sail from the glorious Sag Harbor. It’s the perfect laidback Hamptons evening – and unlike virtually everything else in the Hamptons, this cruise is considerably less expensive because you can bring your own beverages.

It really is a special way to soak in the transition from afternoon to evening, and you’ll still have plenty of time to enjoy the bar and club scene in the Hamptons. Make sure to book the sunset cruise on the American Beauty II well in advance because it’s becoming quite the popular activity in the summer.

8. Join the party at The Surf Lodge

The Hamptons is far from being a quiet, oceanside region where everybody keeps to themselves. It’s quite the opposite: for every age group, the Hamptons is a place to see and be seen, dress up and party. There is nothing that captures that Hamptons lifestyle quite like spending a day partying at The Surf Lodge. This is the Hamptons institution which – indisputably – epitomizes the party side of the Hamptons.

Some of the most well-known musical acts and DJs have played in this small, outdoor venue which have catapulted it into a level of stardom of its own. What really makes The Surf Lodge special is that you can get up close and personal with the big-name acts that play at the venue. You’re more or less getting an intimate sunset concert that you would be hard pressed to find at any other venue around the world which is why The Surf Lodge has cemented its position as one of the best clubs in the Hamptons.

Getting a table or a ticket to enter The Surf Lodge can be a challenge. Be prepared to fork out more than you expect – and certainly more than is reasonable – for a ticket to enter The Surf Lodge. You’ll also need to be quick on the game because their events tend to sell out at breakneck speed.

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9. Get gourmet takeaway food (and pies!) at Round Swamp Farm

The Hamptons is littered with farm stands serving delicious food, but no Hamptons local or frequent visitor would disagree with our view that Round Swamp Farm stands out above the rest in virtually every category, whether it be quality, variety, design, experience or otherwise. It’s truly a wonderland of tasty gourmet foods that you just can’t help being excited about.

The food is on the whole absolutely spectacular. This is the type of food takeaway that will make you wonder why everywhere can’t sell the same quality of food.

A word of warning: Round Swamp Farm is painfully expensive. It’s in the same league as eateries in the Hamptons that sell guacamole for US$29.

I consider myself a dessert connoisseur of the highest order, so when I say that the pies at Round Swamp Farm are the best in the Hamptons and probably some of the best in the tri-state area, don’t take it with a grain of salt: take your wallet to Round Swamp Farm and experience it for yourself. Make sure to go early in the morning if you don’t want to miss out on their peach pie.

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