Montauk, NY

I recently turned the big 3-0, wooo! Originally the plan was for a group of our girlfriends to get together and go on a trip to celebrate, but given the world is in shambles we were unable to do so. BUT, I was still able to make the best of it and go away to Montauk with my boyfriend for a long weekend. This was my first time exploring the Hamptons so I was a little excited to say the least. We stayed in Montauk for four nights and it was a jam packed trip so this post might be a little lengthy- but worth it!

Wolffer Estate Vineyard

We drove out to Montauk which only took a couple of hours given we’ve been staying on Long Island, but you can also take the train too. On our way out there we stopped at Wolffer Estate Vineyard for a wine tasting. We were able to reserve a table a few days prior and enjoyed some delicious rosé, summer white wine, and a cheeseboard. The estate is absolutely gorgeous, if you’re in the area I highly recommend you go check it out. From the vineyard we continued our drive to Montauk and stopped at Lunch for an amazing lobster roll and fries. We called in our order which was a great idea as there were lots of people lined up and waiting for their orders. 

Navy Beach

We finally made it to Montauk and did a contactless check in to our hotel, Aqualina. The hotel was just what we needed, it was right in town, a very cute room, pool and quartyard area, and right across the street from the beach. After we checked in, we walked over to Montauk Brewing Company for some beers. They were only serving to go so we went across the street to the park and sat on the grass and enjoyed them. Not sure if that’s legal but nobody bothered us! For dinner we took an uber over to Navy Beach which has a great view of Fort Pond Bay for the sunset. The food and cocktails were really good and the sunset was beautiful.

The next day (my actual birthday, yay!) we woke up and went straight to Montauk Bake Shoppe. You MUST go to this bake shop if you have any desire for pastries, breakfast sandwiches, heck any type of sandwich. This place was amazing, I cannot say enough nice things about it. We got croissant breakfast sandwiches, and a mini key lime pie and lemon bar for my birthday “cake”. FYI my favorite dessert is anything lemon. Everything was so good we ended up going back our last morning in Montauk and getting a whole box of things to take back. They are known for their jelly croissants which I got the second time around and I regret not buying a dozen of them, they’re to die for!! 

Jelly Croissant
Key lime pie & lemon bar
Croissant breakfast sandwich

After indulging at the bake shoppe we went to Ditch Plains beach for the day. We had to drive to get there but it’s definitely worth it. Just note that in order to park in the beach lot you need a pass, you will get a ticket if you don’t have one. Ditch Plains is a beautiful beach, tons of surfers everywhere, and you get a beautiful view of the cliffs. There is a food truck in one of the parking lots called Ditch Witch, we ate lunch here and got a lobster roll. It was pretty good, wish we would’ve tried more food but I was still stuffed from the bake shoppe. We made a pit stop at the lighthouse on our way back from the beach. You have to pay for parking here but the lighthouse is a Montauk staple. You can walk along the dirt path to get a good view/picture of the lighthouse rather than paying to get on the property (you have to pay for parking + separately pay for entrance). 

Ditch Witch food truck
park at the lighthouse

For my birthday dinner we went to Showfish, a new restaurant at the Gurney’s Resort on Star Island. This property is right on the water with boats docked right next to you. The service and food were both amazing. We ordered so much food, you only turn 30 once! We got oysters, shrimp cocktail, lobster tagliatelle, lobster and kimchi fried rice, and the whole lobster. Along with some cocktails of course! We walked around the property and through the docks during sunset, it was the best birthday dinner I’ve ever had. 

Gurney’s Star Island

The next morning we went to Bluestone Lane for coffee and breakfast, another croissant sandwich for me! The coffee was very good here, the sandwich was ehhh compared to the bake shoppe in my opinion. After breakfast we went to Shadmoor State Park for a little hiking. The Shadmoor trails take you to the top of the bluffs where you are overlooking Ditch Plains beach. It is a gorgeous view, reminds me a lot of the cliffs in San Diego so I was feeling very nostalgic. The hike is not strenuous at all, there are also multiple trails though so you can get a decent workout in. 

Shadmoor State Park

Although Montauk seems like a very small town, there was plenty to do to keep us busy. There are lots of cute boutiques to go shopping in. Some of my favorites were Wyld Blue, Indy Home Design, and Montauk Clothing Company. Another great trail that we did that was a little bit longer and more strenuous was Amsterdam Beach Trail. This trail takes you up to a lookout point and also down to the beach, just be sure to watch out for ticks! We also went to Gosman’s for lunch one day. There’s a few different places you can eat at Gosman’s, we went to the rooftop which had great views of boats passing by. On our last night we had dinner at South Edison, the food was very good and the cocktails were great as well. We also spent a couple of full days just lounging on the beach, we brought a cooler filled with snacks and drinks and it was absolutely perfect and so relaxing. 

“Yeah I’m drinking, Luann” -Tinsley
Bluestone Lane Coffee

One thing I learned from this trip, which may be due to Covid, is that you need a reservation at most of these places and you need to make it in advance. Also, a lot of the restaurants were “first come first serve” and would literally fill up their waiting list the second they opened. Next time I definitely want to try Harvest and Montauket, both restaurants with sunset views that were impossible to get a table at. I also want to go to Gurney’s Montauk once the spa reopens, it’s supposed to be one of the best spas on Long Island and have great restaurants and beach scene. The Surf Lodge, which you may have heard of before because it’s known for celebrity sightings, was closed only to those staying at their small hotel. That was a bummer, it’s supposed to be a fun place to go to. 

I had such a great and relaxing time in Montauk. The town is so laid back and it doesn’t feel like you’re even in New York anymore. Although this year isn’t turning out as we thought it would, I’m still extremely thankful for these experiences and can’t wait for more in the future. 


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