Over the past few years, Montauk has grown in popularity as a summer destination - not only for New Yorkers, not even for east coasters, but actually receiving travelers from all over the country and the world.

It used to be a small and quiet beach town, about 3.5 hours east of New York City and commonly referred to as “The End” as in The End of Long Island. The area is known for beautiful beaches and great surfing.

My parents would drive out to The End for day trips to the beach when they were young, and spend hours in the sand and sun on Hither Hills. My best friend Mel’s family vacationed there in the summer too. And though everyone spoke so highly of it, I never explored Montauk myself until about six years ago when we did a girls weekend. We were young and spent the whole time going out, drinking at the old Sloppy Tuna happy hour and dancing at the bars.

Since then I’ve gone back many times, and love it more with each visit. The best is getting the chance to explore more beyond the beach or town, and spending a great weekend with friends in such a beautiful place. So here is my itinerary for a few weekend in Montauk!

Getting There

By car: The drive is about 3.5 hours from NYC, and having a car is most comfortable for the ride but its also great to have a car while you’re out there. There is usually some traffic in traveling through the Hamptons on the one lane Montauk Highway. And there will always be some traffic on summer weekends so plan accordingly.
By Bus: The most common is the Hampton Jitney, which picks up in Midtown and drops passengers off in various towns through the Hamptons. Montauk is the last one! It’s a pretty comfortable way to travel, and there is a bathroom. This is about $30 each way.
By Train: The last stop on the LIRR Montauk Branch is Montauk station. The train gets packed on summer weekends, so get on early and grab your seat! This is also about $30 each way.

Where To Stay

Renting a House

This is my favorite option. More space and privacy! There are plenty of rentals listed on Airbnb and VRBO but with they seem to get booked up months before the summer! This year my friends found a home nestled between Montauk Highway and Old Montauk Highway, and just a short walk to the beach! It was really ideal with a large kitchen and living room for big meals together, a heated in-ground pool, a large sun deck, an outdoor shower, and a fire pit.

When renting make sure you are looking at the area, because Montauk is pretty spread out! Many homes are far from town so you’ll need a car or will have to rely on Ubers.

Hotels

There are many good options in Montauk, which I broke out by price and quality. You’ll see that even the accommodations in the ‘Save’ category are still not cheap. There is high demand and that means higher prices!

Splurge

Stay

Save

One of my visits we stayed at the Montauk Lake Club. It’s beautiful, and has a great pool and lake access at the marina. One of my closest friends got married here last year so it will always have a lot of great memories for me!

Day One

First we immediately hit the beach! We decided to go to Kirk beach which is an easy walk from town. We enjoyed eating lunch and watching some whales in the distance.

There are some great take out lunch spots to choose from in town, here are a few I recommend:

Goldberg’s: Amazing sandwiches and bagels, I end up eating it once a day in a typical Montauk weekend
Joni’s: Healthy but delicious options, ranging from sandwiches, wraps, salads and smoothies. Usually has a line!
Naturally Good Cafe: Healthy and organic, great for smoothies and juices
Round Swamp Market: Groceries, fresh produce, and pre-made dishes

Once you’ve had some lunch, you can stop by Bounce Beach MTK for happy hour drinks!

Next stroll through town, exploring all the cute shops and home stores! Don’t be embarrassed if you end up with a Montauk sweatshirt, I don’t know why but thats pretty common.

For dinner, we went Duryea’s Lobster Deck. The outdoor deck is beautiful overlooking the water, and a perfect location to watch the sun set. Even after sundown the mood is still set with tons of string lights and candles.

The food here is delicious. Everyone raves about the lobster rolls and the famous lobster cob salad! This place can often have a wait, but it’s worth it. I highly recommend putting your name in, getting some drinks and fried calamari until your table is ready.

We ended the night with some wine at the house and relaxing by the fire pit!

Day Two

Wake up and grab some coffee and breakfast in town somewhere like Hampton Coffee Company or Montauk Bake Shoppe.

Then take a drive to explore the Montauk Lighthouse! This is the farthest point, and such a beautiful view. You have to pay for parking, and when we got there it was so windy that we decided to nix paying for the entrance to the lighthouse and museum, and just walk the property instead. We were really happy with that choice!

Then we spent the afternoon enjoying the pool at the house. Even in the end of September, the sun was beating down and made for a comfortable afternoon. We even utilized the slide!

If that’s not an option for you, I suggest a beach day.

In the late afternoon swing by the Montauk Brewery for some beers and fun.

Then pack up a picnic or some drinks and head to the beach for a bonfire at sunset! It’s the best budget friendly happy hour in town :)

Once the sun went down and we got hungry, we ordered in from Harvest on Fort Pond for a nice dinner at home!

Day Three

Start the morning with something active, like a run to the beach or a spin class at Soul Cycle in town! Running down old Montauk highway is fun for spotting some of the most gorgeous homes, and great views of the beach!

Then get ready for a little day trip out of MTK!

You know what rocks about it? No directions needed, you never even have to get off Montauk Highway.

First up is some lunch at either the Lobster Roll of Clam Bar!

Casual food at both places, and everyone loves it! Prepare for a little wait if you are going in high season.

The next stop on this day trip is my favorite, an afternoon at Wölffer Estate Vineyard in Sagaponack!

If you love wine like I do you are going to have a great time here. Their Summer In A Bottle rosé is so delicious. I’ve been several times over the years, and anyone who comes here loves the vibes! Hanging out and having some wine and cheese on the patio looking out at the vines makes for a wonderful activity and afternoon.

You can either do a group tasting through Wölffer, or make your own tasting by getting a bottle of wine for the table and trying various kinds!

If you can’t get a reservation at the vineyard, at least stop by the wine stand next door! The best part? It’s a drive-thru! You can pick up some of their wine, liquor or ciders without even getting out of the car.

On the way home, stop by Amber Waves in Amagansett! An adorable ocean-side farm with a large variety of fresh produce straight from their on-site garden! I came here for the first time when I was in middle school, and still remember their delicious breakfast and having a warm scone in their cute outdoor garden. I love going back and seeing that they are still such a successful small business!

You can grab coffee and a hot beverage in the mornings, or fresh ingredients for cooking up a delicious homemade dinner that night. They also have a variety of local wines, and jelly.

I love a good farmers market, but this farm stand is one of the best I’ve ever been to. Don’t miss it!

Take yourself on a tour of the garden before you leave. We literally picked a baby tomato or two off the vine, and oh my goodness the freshness and taste! When you get home make yourself some divine fresh caprese sandwich and guacamole.

Dining

There are so many great restaurants in Montauk. Here are a few of my favorites!

Best Dining and Views

Harvest on Fort Pond - delicious food and on the water
Navy Beach - fresh seafood + drinks on the beach
Crow’s Nest - sunset happy hour on the water (pictures below)
Montauket - sunset happy hour on the water
Duryea’s Lobster Deck - delicious seafood and the famous lobster cobb salad
Scarpetta Beach - this spot is delicious and has swanky vibes. Love going out at Gurney’s afterward.
Showfish - great food and beautiful water views, located at Gurney’s at Star Island

More options around town

Sel Rose - pretty restaurant and good food, great for groups
668 Gig Shack - fun and cute! Has a small patio and sometimes live music
TT’s - very grammable restaurant with some outdoor dining as well
Salivar’s Clam and Chowder House - great seafood
The Dock - dive bar vibes but cool food and good value

Coffee Shops

Casual Bites

Sausages - Best pizza! Get the buffalo chicken pie
Pizza Village - Could be the drinks talking after hours at the Point, but this pizza is key for late night
MTK Street Food - Casual seafood
Anthony’s Pancake House - Great for Breakfast
Johns Pancake House - Great for Breakfast
Johns Drive In - Burgers and Ice Cream

Spots for Drinks & Going Out

Montauk is a TON OF FUN. Here are some of the best places to go out.

Ruschmeyers - outdoor camp grounds vibes with fun music
The Point - sports bar
Memory Motel - dive bar dance party
Surf Lodge - dining + drinks
Lynn’s Hula Hut - has live music!
Shagwong - late night dive!

See how much fun you can have out East? So what are you waiting for - book yourself a weekend!

And it’s not too late. I highly recommend planning a trip this Fall, because even though Montauk in the summer is my favorite, there is so much to still do in the Hamptons in October and November.

Xx Gab

Visits Out East

I’ve made quite a few trips out to Montauk over the years, and while I may not have done a house for a whole summer I’ve certainly spent a lot of long weekends and explored most of the town by now. Whether it’s dining at the best restaurants, finding gifts at the shops in town, hitting a beach bar after a day on the sand, or sipping drinks at happy hours and dancing the night away. Montauk has always been a favorite summer destination.

Montauk