A Long Weekend in Montauk, New York

A long weekend in Montauk, New York is just the way to spend a perfect summer in the Hamptons. Montauk is the eastern most tip of the Hamptons and even gets the name “Montauk: End of the World” because of it’s location. You’ve probably heard of this summer destination from a New York friend who visits every summer or you might have seen your favorite influencer visit or you’re like me and love watching Summer House.

Montauk and the Hamptons have quite the reputation. It houses some of New York City’s wealthiest people for the summer. Even if you could care less about all of that, Montauk is an IT destination. It’s no wonder it has been named one of the most expensive travel destinations in the United States. While it will cost you a pretty penny, Montauk has just the right amount of beach town charm to make it worth your while. Take a look at where to stay and what to do in Montauk, New York for a perfect weekend getaway.

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If you already live in New York City or New Jersey, getting to the Hamptons will already be ten times easier than someone traveling out of state. The best airport to fly into when traveling to the Hamptons or Montauk, New York is JFK airport. And, for those who can swing it there is the East Hampton airport that’s meant only for private charters and smaller airplanes. Once you’ve arrived in NYC, you have three options to get to Montauk:

• By car: renting a car gives you the most freedom of all the options but you will run into traffic depending on what time you head over!
• By train: the Long Island Railroad is a great option for people who want to avoid traffic. It’s about a 2-hour journey.
• By jitney (bus): the Jitney is a bus line that serves the Tri-State area with multiple pick-up and drop-off locations in the city and Hamptons.

Depending on your budget, I highly recommend renting a car for a weekend trip in Montauk. Not only will you be able to have a bit more control over the trip, but not having a car in the Hamptons makes it so much harder to get around. Montauk is small enough to get to most places by walking or biking but getting to any other part of the Hamptons would be impossible without a car.

I typically use rentalcars.com for the best price and always rent from a reliable company like Hertz. I have never had a bad experience using the Rental Car search engine and it makes my trips super flexible with easy and free cancellation. Use the search engine above to find the best price for your Montauk trip.

Montauk has a plethora of options when choosing where to stay. Airbnb and VRBO are great options for those who are traveling with a big group or large families. For couples and small families, my favorite Montauk properties are listed below:

• Gurney’s
• Hero Beach Club
• Montauk Beach House

You can use the booking finder below to easily find the perfect hotel stay for your weekend in Montauk.

The Hamptons are known for their pristine beaches on the East Coast and Montauk is right up there with having some of the best. For surf lovers, you’ll want to head to Ditch Plains Beach. Kirk Plains Beach is another great spot for those who want to enjoy water sports or just enjoy lounging on the beach all day. If you’re up for a bit of a drive, head to two of the best beaches in East Hampton, Coopers Beach or Main Beach.

You absolutely cannot go to the Hamptons and miss out on some shopping! I don’t care who you are. While Montauk has more surf shops mixed with boutiques, those looking for high-end shopping will want to head to South Hampton and East Hampton. However you can still find some great local shopping in every town along the Hamptons like Obligato and Everything but Water.

Montauk has the reputation of being a bit of a party animal and that’s due in large part because of places like the Surf Lodge. The Surf Lodge is a restaurant, hotel and music venue all in one and is known for bringing in the best artists. The only problem with the Surf Lodge is getting in. If you are dead set on going then some foolproof ways of getting inside are arriving super early so you are one of the first people in line or snag a dinner reservation (which are also hard to come by). We were able to get a dinner reservation and ended up staying after for the music. They really aren’t lying when they say the Surf Lodge is the place to see and be seen. Plus, it’s an overall great place for live music and to dance all night.

Gurney’s has it all. It’s a resort with one of the best spas in the Hamptons, Scarpetta, an exclusive beach and now they even have their late-night fire pits. The fire pits are a place to grab a drink, make a s’more and enjoy some music after dinner. Like most places in the Hamptons, it’s also very hard to get into unless you’re prepared to drop some serious cash on a table. However, if you get there at just the right time you can grab an available seat just as someone’s leaving.

Summer in a bottle is made here. And, yes I am talking about the wine. Summer and rose go hand in hand and Wolffer found a perfect mashup of the two to produce their well-known Summer in a bottle rose. Book a reservation in advance to enjoy a flight of wine or a glass or two among the vineyards. This makes for a perfect afternoon in the Hamptons.

If you have time, I recommend spending a few hours on the water. There are many local charter companies that will take you on a sunset sail or afternoon trip on the water for a few hours. While we didn’t have enough time, we looked into and would definitely book with Cruise Montauk next time.

The Hamptons are known for their lavish pool parties since every house comes with one. If you’re lucky enough to be staying at a house then enjoy some downtime at the pool or maybe you’ll enjoy it Summer House style and have an all out party.

The Hamptons have great food options with upscale restaurants mixed in with local shops that will make you want to visit more than once. Take a look at some of our favorite restaurants in the Hamptons.

Lunch (aka Lobster Roll) is legendary in the Hamptons. They have, you guessed it, the best lobster rolls. The original location is near Montauk with a new restaurant opened in South Hampton. You’ll be in for a wait if you head here nearly anytime after it opens. We happened to get here 5 minutes before it opened and were able to get in right way. I recommend doing the same for no-wait.

The name says it all. Goldberg’s bagels needs to be put in the Hall of Fame for how much I loved them. We went there twice because we loved their bagel sandwich so much. This is a can’t miss for bagel lovers but you should prepare for another long wait. And, don’t forget to grab a cup of joe with your bagel at Left Hand Coffee fright down the street.

One of the coolest outdoor restaurants is Dopo La Spagia. Book in advance for some great Italian food and even better atmosphere.

Great view of the ocean while you eat? Count me in. This restaurant is located in the spectacular Gurney’s Resort. This is the sister restaurant to Manhattan’s Scarpetta and it doesn’t disappoint.

We absolutely loved breakfast at Joni’s. Everything here is made fresh and you won’t want to miss their smoothies!

• Duryea’s
• Navy Beach
• Naturally Good
• The Crow’s Nest

I already mentioned Surf Lodge and Bounce Beach as having some of the best party scenes in Montauk, New York but you can always keep the party going at any of these:

• Montauket
• Rushmeyers
• Liar’s
• South Hampton Social
• Muse @ The End

I hope this itinerary helps you plan a perfect weekend in Montauk, New York. For other travel inspiration similar to the Hamptons, check out my weekend guide to Palm Springs. And if you ever have questions or need travel advice, reach out on Instagram!