So You Wanna Go to the Hamptons? Your Guide to Montauk

Posted August 14, 2017 by Elena in New York City / 0 Comments

One of the New York-iest things one can possibly do is actually…leave New York. To the Hamptons, that is! 

The Hamptons aren’t just for wealthy, well-connected WASPs, as I once naively believed. New Yorkers of all stripes go there summer after summer. It has a scene for almost anyone, and with the right planning and research, you’ll find yours too!

As a California girl and an uber-fan of Showtime’s The Affair, I was always attracted to Montauk in particular. The farthest of all the Hamptons, Montauk is located on the very end of Long Island, and is affectionately referred to as “The End of the World”. Known for its surf scene and laid-back yet chic vibe, it’s quickly become one of New York’s trendiest summer destinations. And it’s awesome!

Whether it’s your first time heading out there or you’re just looking for some fresh tips, here’s my guide to Montauk.

Getting there
What to pack
Where to eat, drink and play


There are two popular options for getting to Montauk: the Long Island Railroad or the Hampton Jitney.

The Long Island Rail Road (LIRR) will cost you $29.25 each way and get you there in just over three hours. My tips:

  • Buy your ticket in advance using the MTA eTix app. Kiosk lines at the stations can be long and cause you to miss your train.
  • Avoid buying a round-trip ticket. You could end up extending your trip or taking an alternate means of transportation home. You may even meet the man of your dreams and he’ll offer to fly you back to the city in his helicopter. You never know! Give yourself options and stick with the one-way ticket.
  • It’s a long ride, so bring some entertainment. It’s a great time to watch a movie, catch up on a TV show or read a book (check out my Reads page for book recs!). OR…
  • Be social! On holiday weekends especially, the LIRR to the Hamptons is a giant party train. Don’t be surprised if you can’t even find a seat and people are indiscreetly passing around booze. You might as well make some friends, and maybe even hang with them over the weekend!

The Hampton Jitney, as you may recognize from Sex and the City, is a charter bus that will take you to and from the Hamptons. It’s $28 each way and, unlike the LIRR, makes minimal stops along the way, so it’ll get you to Montauk in less than three hours without traffic. You’re also guaranteed a seat, which is a plus on holiday weekends. 

Image via Flickr

The Jitney is more comfy and streamlined than the LIRR. However, the LIRR is more fun and social, especially if you ride with your friends. It’s a personal preference. You do you!

What to Pack

I love Montauk because I can dress like the California girl that I am and not look out of place. Just like the vibes, the style there is casual and beachy, yet chic. It is the Hamptons, but don’t be intimidated by the fashion.

A weekender bag or suitcase is all you’ll need. Here are some must-brings:

  • Tote bag. Perfect for daytime and the beach.
  • Small pursue or clutch. All you really need when you go out at night is your keys, ID, money, phone and charger. No need for a clunky tote bag, especially while you’re dancing the night away.
  • Sandals, sandals, sandals. Don’t bother with heels or even wedges. After waiting in line to get into Ruschmeyer’s or The Surf Lodge (more on those in a bit), and then doing more waiting in the bathroom line once you enter, you’ll be wishing you kept your Sam Edelman flats on. They’ll take up less room in your luggage too!
  • Sundresses, rompers, shorts and tanktops
  • One-piece bathing suit. I’m loving the one-piece revival happening right now. Pair it with cute shorts or a skirt and you can start your night straight from the beach.
  • Light sweaters and outwear. The weather in Montauk is…unpredictable, to say the least. Some days it’s 80 degrees without a cloud in the sky, while other days it rains and looks like doomsday is near (hey…they do call it The End of the World). Check the weather diligently and bring some light sweaters and jackets just in case.
  • Umbrella. Again: summer rain is a fact of life on the East Coast. Be prepared.
  • Flip flops. They may the worst possible shoes to wear in New York City, but they’re so convenient in Montauk for quick outings, the beach or the pool.
  • Workout clothes and shoes. Montauk is a great place to sweat it out, if you’re into that while on vacation. Go for a beach jog or hit up a class at SoulCycle
  • Books. Because there’s no better beach companion.
  • Sunscreen
  • Bug repellant and anti-itch cream. The bugs on Long Island are no joke.

Where to Eat, Drink and Play

Ruschmeyer’s – Great daytime or nighttime spot, with an awesome outdoor area complete with picnic tables and a firepit. 

The Surf Lodge – A true Montauk staple. Getting in at nighttime is like getting into Fort Knox, however, so plan ahead. Your best bet is to make a dinner reservation, get there with your entire party right on time, and then stay through the night.

PRO TIP: Go to the bathroom before you get there. The restroom lines are longer than the lines to get in.

Navy Beach – Come for gorgeous sunset views right on the water.

668 The Gig Shack – A local favorite with fantastic food, perfect for lunch on a sunny day. 

Solé East – Killer food and drinks and an even more killer aesthetic. Has a lovely outdoor seating area with plenty of string lights at nighttime. 

The Sloppy Tuna – Rowdy daytime spot with a fitting name. Located right on the beach.

The Montauk Beach House – Never gets too crowded and always has a live DJ.

Gurney’s – Definitely bougie, but there’s no better beachfront spot in Montauk. Wear your bathing suit!

Grey Lady – Fun nighttime spot with a nautical, New England feel.


There’s still plenty of time to head Out East this summer. Let me know in the comments if you have any favorite spots I didn’t mention!

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