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Montauk Weekend Getaway | The Perfect 3 Day Itinerary for a Weekend in Montauk

Shadmoor cliffs in montauk new york at sunrise overlooking the ocean.

Montauk has a really special place in my heart and it should have a place in yours too! A small fishing village, a surfing town, a family beach vacation, a weekend getaway – Montauk means a lot of different things to a lot of different people.  To me, Montauk is home.  There is a good reason thousands of people decide to spend a weekend in Montauk each summer – it is a truly special and beautiful place.

Keep reading for my 3 Day Itinerary Guide for a Montauk Weekend Getaway including what to do in Montauk, where to eat and drink, and where to stay.

Read my other weekend getaway guides here: Tulum, Mexico, Rincon, P.R. & North Shore, Oahu.

girl wearing denim shorts standing in middle of road with sunrising behind her. weekend in Montauk

Where to Stay for a Weekend in Montauk

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Ditch Plains Beach.  Dark clouds over the beach.

Montauk Weekend Getaway

Montauk has so many great restaurants and places that I haven’t included on this list.  This post is meant to be a guide to help you plan your best weekend in Montauk. Read below for my suggested 3 day Montauk weekend getaway itinerary!

Day 1

  • If you’ve arrived the night before, I suggest grabbing a coffee or light breakfast at Blue Stone Lane and taking a walk in Shadmoor State Park.  My favorite walk to leads you on top of the buffs with Ditch Plains as your backdrop as you walk East.  The whole walk is about 2+ miles there and back.  (click here for a list of the 8 best walks and hikes in Montauk)
Girl on edge of cliffs in Montauk NY watching the ocean and waves at Shamoor state park.
Girl on edge of cliffs in Montauk NY watching the ocean and waves at Shamoor state park.
  • If you’re up for exploring a bit more, head to the Montauk Lighthouse & Camp Hero State Park for a bit of history and amazing ocean views.  Commissioned by George Washington in 1792 and completed in 1796 the lighthouse still serves as a navigation tool.  Camp Hero served as a military base for many years and old bunkers, a Radar tower, and some dwellings still exist in the park.
Montauk Lighthouse
  • You’ve come to Montauk to enjoy the beach!  The best beaches are in town with free parking for anyone.  Read my guide to the best beaches in Montauk here.
Montauk Beach
  • If you need a casual late lunch (or a few afternoon margaritas) TT’s or Hideaway is your answer.  
mexican corn and watermelon margarita
  • Or you can grab a quick slice at Blade + Salt before heading off to watch the sunset.
  • You can’t miss a Montauk sunset!  The Montauket has some of the best views over Fort Pond Bay.
  • After you’ve watched the sun set into the Long Island Sound and had yourself a few drinks – head into town to enjoy a great dinner.  I love 668 The Gig Shack for smaller bites (although they have amazing entrees too) & The Harvest for a group dinner served family style – try to sit outside in the garden if you can!

Planning more than just a weekend? Read my Complete Montauk Travel Guide here!

Day 2

  •  Craving a refreshing acai bowl?  Get to Happy Bowls for a morning acai bowl where you can choose your toppings.
What to do in Montauk - happy bowls acai bowl
  • Have an uber or cab drop you off at Ditch Plains for the day.  You must have a parking sticker to park in the parking lots and you will get hit with a nice parking ticket if you choose to park without one.  (don’t be that person)
  • Get Ditch Witch for lunch!  It’s my all time favorite food truck.  One of my favorites is the sesame noodles and you can add poke on top if your little heart desires.  Cash only!
Ditch Witch Montauk food truck at Ditch Plains Beach

Shop Summer Label swimwear here.

  • After baking all day under the hot summer sun, you’ll want a mudslide from Liar’s to cool you down.  Be mindful that these may not taste strong but they are!  Liar’s is Montauk’s famous dive bar located in the marina.  Cash only!
What to do in Montauk - liars saloon
  • For sunset and dinner I recommend two places: Crow’s Nest & Inlet Seafood.
  • Inlet Seafood is a second story restaurant over looking the jetty with a perfect view of the sunset.  The restaurant has amazing sushi as well as a range of appetizers and entrees.
  • If you decide to come to the Crow’s Nest, come on the earlier side to ensure you will get a table.  Walk down to the beach bar, on the shore of Lake Montauk, to enjoy a watermelon cooler and watch the sky change color as the sun sets and you wait for your table.  The food is amazing – the whipped ricotta is a must!
  • Of course nothing beats an at home BBQ or beach picnic to watch the sunset!
Two people watching the sunset at navy road in Montauk NY over looking Fort Pond Bay

Day 3

  • Are you hungover? Goldberg’s Bagels will help you out.  Order a flagel – a flat bagel that gets nice and crispy when toasted.
  • Montauk’s main attraction is the beach – you can pack a great lunch from Joni’s and head to the beach for the day.
  • In the afternoon be sure to hit up Montauk Brewing Company for a cold beer!  They always have new beers on tap to try and you’re always guaranteed to have a great time here! (plus I work here :))
Weekend in Montauk - Red brewery barn of Montauk Brewing Company with american flag in front of building
  • If shopping is more your thing.. walk around town and discover so many great little boutiques.
  • If you’ve decided to extend your weekend in Montauk and stay Sunday night, enjoy live music at the Surf Lodge or reggae night at Liars Saloon.  Both a great time!
  • End your evening with my favorite restaurant, The Dock.  It’s a Montauk staple!  Located at Town Dock, The Dock restaurant is a great little tavern-esq place.  Simple food, but amazing food.  I seriously love the whole menu but some of my favorites are: Jalepeno Poppers, Mussels, Clams Casino, Tuna Melt, Chili, Vegetarian Sandwich and the specials are always good.


  • Coming in the off season?  Read my Off Season Guide to Montauk for the best things to do in the Winter, Spring and Fall.
  • Click here for the most photograph worthy and instagrammable spots in Montauk.
  • Montauk is about a 3 hour drive my NYC however, in the Summer months you can hit tremendous traffic.
  • If you don’t drive out, the best way to get to Montauk is by the LIRR (train) or the Hampton Jitney bus.
  • The closest airport is ISP but most flights will come into JFK or LGA.
  • If you are coming from New England, there is a ferry from New London, CT on the Viking Fleet.
  • Montauk is an expensive place to visit.  Expect cocktails and wine to be close to $15 and entrees at restaurants to be over $30.  Cabs and Ubers are also expensive but worth the alternative 🙂
  • You can’t park at Ditch Plains unless you have a parking permit.
  • Always be respectful of the environment. Montauk is a beautiful place, let’s keep it that way!
girl in white dress and guy wearing shorts looking out to the ocean on the beach in Montauk

Planning a trip to Montauk? Read my Complete Locals Guide to Montauk or download the free guide below!

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Ariana Jasuta

Hi! My name is Ariana and I'm from Montauk, NY. I started this blog as a way to share my passion for traveling and capturing a place with photographs. I love helping others plan their travels so feel free to reach out to me! xx Ariana



  • Virginia - Ginnie Davis

    Very informative and clear, nice variety in all categories. Keep it going!!
    Lovely photos

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