Montauk: Weekend Escape from NYC

For our girls trip this year, we decided to make it a little more low-key and escape on a road trip instead of flying since we were all traveling to Punta Cana for our friend's wedding in the Fall.  We were deciding between a few destinations but landed upon Montauk!  I had only been there once before and no one else had been so it was a perfect opportunity!  Since we weren't spending money on a flight, we decided to spend a little extra on the hotel and ended up getting a really good deal through Booking.com.  Traveling out East from the NYC area gets very crowded on the weekend so we traveled Sat-Mon to beat the traffic.  Keep reading to find out all of our favorite spots!

Day 1: Saturday

We arrived at Montauk right before lunchtime and luckily our room was ready early! We stayed at Gurney’s Star Island Resort, not to be confused with the OG Gurney's! We might have accidentally went there first thinking it’s where we were staying and after figuring out there was another Gurney’s (who knew!) we drove up to our correct location and was so delighted with the hotel.  We had a beautiful room with a giant bathroom/closet including an outside sitting area that opened right onto the dock since we were on the bay side. It was perfect for the four of us! Since it was a gorgeous sunny day, we drove to grab some wine and headed to the beach for the rest of the day. If you do stay at either Gurney’s, there is a complimentary boat ride every Saturday at 2pm that we didn’t know about until afterwards but would definitely take advantage of it in the future!  We munched on some pizza and a Mediterranean plate from the hotel’s restaurant before heading back to the room to change for dinner at Navy Beach. We heard this was the perfect outdoor dinner spot for a sunset dinner on the beach and we were all for it! Our table was essentially a giant couch on the beach and we had a front row view of the sunset. We shared a ton of plates as well as a couple bottles of wine and had an amazing time. The mac and cheese was one of our favorites! After, we did a little bar hopping before ending at The Sloppy Tuna for a bit then The Point.

Day 2:  Sunday

The sun was out again for another perfect day so we decided to indulge in egg sandwiches and avocado toast at Tillie’s, which is located in the other Gurney’s, before taking advantage of their amenities!  Even though we didn’t use it, the hotel has a shuttle that brings you back and forth between both Gurney’s so you can use the amenities at both locations! We were set up with complimentary beach chairs and towels and sipped on the new Gurney’s beer and pina coladas for the next few hours.  After enjoying the sun and walking along the beach, we headed back to our hotel room to get ready for the rest of our activities of the day! Our first stop was the Montauk Lighthouse. We went after it closed (free parking) so we walked around a little bit and and enjoyed the view. Our next stop was Montauk Brewing Co which is perfect in the Summer since it has a bigger outdoor area than it does inside and you can bring your own food!  We stopped at Tacombi for a little taco appetizer beforehand and brought it with us to the brewery. The brewery also allows dogs so we made a couple friends. 🙂 We went back to the hotel to change for dinner at The Crow's Nest. We originally were going to South Edison but heard that if you could get a table at The Crow’s Nest, you should definitely do it. They don't take reservations but we were able to walk right in and snag a table before it got super busy.   The lobster fettuccine was the highlight of the dinner - it is a must get! It’s massive so we ordered that and a few other dishes and shared plates again so we could taste everything! We stayed there for hours eating, drinking, talking and laughing - it was a perfect dinner and we were so glad we took a risk and went. We went to Surf Lodge for a bit and then ended up going back to our hotel and our plan was to hang by the fire pit but we ran into a wedding after party that we may or may not have accidentally crashed! 

Day 3: Monday: 

Since it was our last day and a bit cloudy, we skipped the beach and explored the main part of town.  Our first stop was the cutest coffee shop, Bluestone Lane, which also doubles as a boutique clothing store!  We visited Vintage Pink next which had everything a girl could want - we could have spent half the day there admiring everything!  Only a small breakfast was needed since we were having a big early lunch so we grabbed a couple pastries from Montauk Bake Shoppe including their famous jelly croissant!  After walking around a bit more, we made our way to Lobster Roll aka LUNCH (otherwise known as the restaurant on The Affair!). It gets packed very easily so we made sure to get there exactly when it opened. We were in a bit of lobster heaven from the yummy lobster rolls we had!  Our next and last stop of our girls weekend was Wolffer Estate Vineyard in Sagaponack. This gorgeous winery also gets very crowded so it was perfect that we saved it for a weekday when everyone was back to work! We sat outside on their beautiful patio and enjoyed a flight of wine while looking out to the vines which was the perfect ending to our trip.  Of course we had to buy some bottles to take home (their table rose is one of our favorites!) so we loaded up the car and headed back home.

Breakdown of our favorite spots and some we wish we explored (in no particular order):

Breakfast/Coffee:

  1. Montauk Bake Shoppe - jelly croissant
  2. Bluestone Lane
  3. Left Hand Coffee
  4. Joni’s
  5. Tilley’s

Lunch: 

  1. Tacombi - tacos
  2. Lobster Roll aka LUNCH
  3. Gig Shack

Dinner:

  1. Navy Beach - go for sunset
  2. The Crow’s Nest - no reservations
  3. South Edison
  4. Scarpetta Beach
  5. Muse @ The End
  6. Swallow East

Ice Cream:

  1. John’s Drive

Nightlife:

  1. The Dock
  2. Hideaway
  3. Surf Lodge
  4. Backyard
  5. Swallow East
  6. The Stephen Talkhouse
  7. The Point
  8. The Sloppy Tuna
  9. Montauket - sunset view

Things to do:

  1. Montauk Brewing Company
  2. Montauk Farmers Market
  3. Montauk Lighthouse & Montauk Point State Park
  4. Montauk Salt Cave (also have one in NYC)
  5. Wolffer Estate Vineyard & Wine Stand
  6. Sagaponack Farm Distillery
  7. Channing Daughters Winery

Need more inspo for your next girls' trip? Check out our Charleston guide!

xo A

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