Returning to Montauk after almost a decade was a surreal experience. The salty ocean, the soft sunsets, the quaint town. Some things alway feel like home.

Derek and I spent a long weekend in Montauk over our anniversary weekend. Especially after the non-stop hustle and bustle of Manhattan, and then the madness that is Penn Station and the Long Island Railroad. Derek wasn’t expecting it, but having witnessed the weekend exodus from the city before, I can’t believe I chose to leave for Montauk on a Friday afternoon. Honestly, can’t recommend it.

Suffice to say, we were ready to kick back with more space and fresh ocean air!

Best advice = hotel on the beach.

We splurged for a hotel right on the beach, the Montauk Blue. The reception staff was super sweet to offer a substantial discount upon our arrival (before even finding out we were celebrating out anniversary). The beach was where we wanted to spend most of our time, and it was wonderful to have easy access via our own private porch, day and night. We also chose this hotel because it is the only in town with an indoor pool. We thought that it might rain, which is common for early June in Montauk. Luckily, it didn’t, but we did spend a lot of time in the pool. The ocean was cold as balls, to put it bluntly. Most everyone actually swimming was a surfer in a wetsuit. The hotel provided beach chairs and umbrellas and after stocking up on snacks, we happily camped out for the day.

My Montauk Must Visit List

Having grown up spending my summers in Montauk, I had a handful of locations that I wanted to visit. Places. had loved or frequented. The funny thing was that once I was there that list sort of slipped away, almost as if the meaning only resonated if I wasn’t actually there. Just being in Montauk gave me the feeling I thought I needed to see specific things to feel. So we didn’t visit everywhere on this list, but there’s time for that, and now we know we will be back. I guarantee Montauk is full of places worth seeing. And feeling. And I believe that if you feel it once, it’ll actually be in your heart forever.

Ditch Plains- this my beach neighborhood back in the day. It’s a couple miles outside town but the beach and bluffs can’t be beat for scenery or watching the surfers. My siblings and I used to pick mussels off the rocks on the jetty. We’d take them home to boil and eat with dinner!
Tacombi- This Mexican restaurant was such a cute vibe for an early casual dinner. We liked being right in town with a great view and I was able to satisfy my Pina Colada craving. That first night in town there was also the most beautiful sunset an we watched it over tacos and chips.
The Crows Nest Restaurant- Recently redone, this restaurant has retained its romantic yet dingy pirate vibe, and is one of the best in town. Closer to Ditch Plains than town, this is a great option after a day at the beach.
Lighthouse- a quaint and cute location to visit at “the point“. I used to know people that would surf off the point, and every time I went there I just couldn’t imagine. Summers only kid here, who never quite found that ocean bravery needed to surf.
Herb’s Market - Derek and I hit this amazing mini grocery and made-to-order deli every morning for amazing egg sandwiches and coffee. We’d take it back to our cozy patio and enjoy them oceanfront. But Herb’s also do catering for lunch and dinner, and have a great selection of beach snacks and beverages. I remember going to Herb’s all the time with my Mom, grabbing stuff for a day at the beach, and ordering full dinners when company came to town. The food is delicious and you get to feel good about supporting a business that has been trusted and successful for so long.
The Surf Lodge- Our cab driver told us on the drive into town that The Surf Lodge lost it’s liquor license until right after Memorial Day weekend, so they were gearing up for their big weekend party. We decided to forgo a huge crowd, but the chic beach club was so popular my last couple summers. I’m definitely excited to visit next time.
Gosman’s Dock Restaurant - This restaurant was a highlight for both Derek and I. The restaurant sits right on the intlet, so we were able to watch the boats go by either entering Lake Montauk or heading towards the sound. The seafood is amazing, obviously, the fish is all caught right there! And the ambience is romantic. My favorite was the baked clams!
Memory Motel Bar- I’ll never forget someone explaining that the bar at the Memory was “the definition of a dive bar“. And then the next summer I came back with a fake ID and I realized that it was still one of Montauk’s best drinking spots. Some things never change.

Now I’ll get sappy.

Revisiting places that felt like home in the past is good for the soul.

I was worried before I went that all the memories would come back. Bad ones too. And they did, but it just didn’t matter. Having Derek there to share the experience kept me so present and joyous. He is always joking, and he even kept the mood light in tough travel situations. Now I see I had to go back to really make peace with the past, hold onto the good, and bring that into the future. Also, I actually can’t wait to go back!