Discover Montauk

Spend a long weekend in Montauk, NY…to some it is a surf town, a fishing village, a romantic get-away or a family vacation. I assure you one thing. You will not be disappointed, keep reading for what do in Montauk for an extended weekend…

Montauk is called “the end of the world” because it is the easternmost point of the island and NY state, it is about a 2.5-hour drive from JFK and I would highly recommended renting a car. Although Montauk is a small town; the resorts, parks, beaches, restaurants and day trips are between 10–30-minute drives apart.

We stayed at Gurney’s Resort. Phenomenal location, stellar service and staff in addition to having a cool, hip vibe at their beach club and the outdoor lounge. I would suggest renting a cabana for one day if you are with a group of people. Or take long walks along the beach right in front of the resort and grab lounge chairs for the day.

Here are the restaurants I would highly recommend.

  • Lunch (aka the Lobster Roll from the famous television series, the AFFAIR)
  • Scarpetta’s Beach inside Gurney’s Resort, outdoor seating and perfect views
  • Navy Beach freshest seafood and the best for sunsets
  • Duryeas for Lobster Salad with water views, sunset and boardwalk seating
  • Sel Rose hip,cool vibe and cuisine
  • Sisi just reopened along the water at EHP, it is in East Hampton but worth the drive
  • Tutto II Giorno in Sag Harbour, a quick 25 minute drive for some of the best Italian ever
  • TT’s in Montauk Harbor for taco’s & tequila after a day fishing or an evening casual bite
  • Surf Lodge is a MUST but make reservations and plan to stay into the night! Amazing sunset, amazing food, cocktails, vibe and scene if you like a dance party to some of the hottest dj’s and bands alike.

Take a day trip to Sag Harbor and stroll Main Street for art galleries, unique clothing boutiques which are lined with restaurants and coffee houses. And if you have the time, take a walk around the marina and darling side streets.  End your day in Sag Harbor at Wolffer Estate winery. Their famous Summer in a Bottle and the Noblesse Oblige Rose are a must. The scenery and ambiance are divine and an absolute must in your weekend to relax, take in the beauty of this magical vineyard to “sip & snack”!

For a spin out on the water, I had a blast on a half day private fishing charter out of the bay into the ocean. Seeing the Montauk Lighthouse from the boat and catching some sun and striped sea bass was awesome. We took our fish to a local hook and cook spot to grill up your catch of the day. Try Kenny at My Joyce Fishing Charters and he will take good care of you and your group!

Our last day we spent 3 hours at Shadmoor State Park, this was an easy hike that leads you to the top of the buffs with Ditch Plains as your backdrop as you walk East.  There are also two “staircases”, that lead you down to the ocean. I would highly recommend this trail if you don’t have time to check out the other half dozen I wanted to! You can’t beat the scenery, the wildflowers and the coastline view.

Spend time walking around the surf town of Montauk itself. Cute shops, coffee houses and a few local boutiques to check out. I suggest the perfectly curated Wyld Blue & Wyld Black.for upscale vintage, unique pieces, home décor, children’s clothes, jewelry, all decorated and hand selected by Sasha Benz.

I wish I had more time in Montauk. Add it to your bucket list, “it is not the end” for me but just the first of many trips back!


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