I’ve lived in New York for my entire life (aside from the past 3 months in Jersey City), and until this summer I had never been to Montauk or anywhere that far out east. My friend Nicole wanted to plan something fun for her birthday, so we got all of our college friends together and planned a trip!
Both Montauk and Amagansett were beautiful and I hope to make it back next summer.
How We Got There
I don’t follow golf, so I had no idea that the US Open was happening this weekend in the Hamptons. My boyfriend warned me the week before so I thought taking the LIRR would be the best option to avoid traffic. It ended up being – hands down- one of the worst travel experiences EVER!! Only 4-5 trains go all the way out to Amagansett every day, so we got a 7:55am train that Friday, thinking we would have a nice peaceful ride. When I got to Penn Station people were pushing and shoving to the platform to get on. I definitely would have preferred sitting in traffic. We took Ubers everywhere throughout the weekend which was fine because we split the cost each time, but it would have been nice to have a car.
Where We Stayed
We ended up finding a reasonably priced Airbnb in Amagansett. The area was beautiful and walking distance to a private bay, but the house was a disaster. It was obviously a cheap house they built just to rent on Airbnb. It wasn’t for us, but it would be decent for a group of 8-10 who don’t want to spend much and don’t plan on staying in the house. I honestly don’t think I would stay there again, but I would recommend it if you have a large group and are looking to spend under $250 each (which is sadly a STEAL for that area). We got lucky because the host also rents out a mansion nearby, where guests get their own limo (!). She graciously offered to have us picked up from the train in the limo, which was hilarious. I was really thankful for that because we were able to stop and get lunch/groceries. The driver told us he could take us around later, but the host quickly messaged me to tell me that we only get one ride, sorry.
Where We Went
I had heard some negative things about this place, and unfortunately we experienced some of that. We headed to the Surf Lodge for dinner on Friday night around 5:30pm. The food, drinks, and atmosphere were great, but we felt SO rushed during dinner! One of my friends even asked the waiter what the problem was. I get it, it’s a popular restaurant and they want to honor all of their reservations on time. But this was next level. We weren’t even done with our food and our waiter scurried over and dropped off the check! We saw the manager/hostess staring us down and felt pretty uncomfortable, even though we had ordered an extra bottle of wine. So, yeah – I don’t recommend eating here because it wasn’t pleasant.
Aside from the dinner incident, the rest of the night was a lot of fun. We got seats at one of the tables right next to the stage and there was a live band all night. To be honest, I’m not sure that I would go back. The whole vibe was a bit pretentious and I could seriously barely fit into the bathroom stall. Also, the hostess still stared us down all night; so bizarre!! We just laughed it off and had a great time. SO great that we ordered pizza when we got home.
Well, we didn’t really go here.. two brave souls took an Uber to the closest bagel shop on Saturday morning to pick up breakfast for the group. The bagels were pretty good, but my friends said the lines were crazy long and that everyone in the store was barefoot (?). Interesting.
We finally got out of the house around noon. We decided to take an Uber over to Montauk and by the time we got there, we were starving. We stumbled upon a beachfront bar which turned out to be the infamous Sloppy Tuna! Since it was the afternoon we didn’t witness the party spot that it apparently turns in to. The lunch was decent but I wouldn’t write home about it, same with the drinks. I got fish tacos and a “Frose.” It was still nice to be sitting outside since it was the perfect weather. After eating we headed down to the beach for a bit.
LOVED this place. I’m not a beer drinker but their drafts were really refreshing. I got the Juice Box IPA and actually enjoyed it. Both the inside and outdoor area are tiny and there is really nowhere to sit, so we just stood at one of the tall boys outside. Some of our group split up and went back to the beach, but I decided to stay. There is a brewery in the back, but no actual tours or anything. The place had a good vibe and the staff was really friendly.
You can take the girls out of the city but we end up going to the exact same places. Yep, we ended up at Tacombi after the brewery and got some drinks and apps. The food was consistent with the Flatiron location, so I can’t complain! I do wish we had tried something new, but I enjoyed the guac and margaritas.
We really wanted to try lobster rolls at one of the cute lobster shacks we passed on our way up, but it would have been a hassle to Uber there. This casual restaurant was right in town, so we decided to grab food to go and bring it back to the house. I got a “Lighthouse Lobster Roll” which is essentially a warm lobster roll, and it was AMAZING. Probably the best meal of the trip.
….AAAND because of all of the eating and drinking we did, we didn’t make it out after dinner on Saturday!! I guess that’s what happens when you’re in your late 20’s and just eat and drink ALL day. We really tried to make it out to Stephen’s Talkhouse but we were all just so exhausted and ended up sitting on the couch and watching the Crown. Still fun!
We finally made it to Amagansett on our last day! This was the cutest little Mexican restaurant with a nice little backyard. We were planning on catching a 1pm train and had all of our luggage with us, so it was perfect. The food was authentic, affordable and delicious. I got a chicken quesadilla and it was perfect.
The Journey Home……
Once again, the LIRR failed us. Our train was cancelled with no explanation, and since there are only 4 trains from Amagansett a day on Sunday we didn’t want to risk waiting for the next one. So, we found a rental car company at the East Hampton airport and the 6 of us squeezed in! 100% driving next time.