Doing Montauk: Family Style!

What was meant to be a quick 2 day getaway, turned into a glorious 5 day family vacation. Never having been to Montauk, I didn’t realize that 2 days there wouldn’t possibly be enough. The weather was perfect, the vibe was incredible, and all 3 members of my little family were having a great time. I’m now a big believer in all things Montauk and hope to make it an annual, summer tradition.
I feel like when you go somewhere for the first time, everything is a bit of trial and error. You ace some of the activities, and others you wish you would have known just wouldn’t be that great. Our trip was pretty impromptu, so we didn’t really do any planning or research when it came to…well, anything. In this post I’m going to include a few great things we did and a few things we weren’t so crazy about.
The first two nights we stayed at a little motel in Montauk Harbor called the Sun N Sound. It was a no frills place with a pool and a kitchenette for added convenience (though it’s not like I actually turned on the stove at any point). The best part was having the ocean right outside your back patio. It was beautiful looking out into the ocean and waking up hearing the waves right from our room. Once we decided to stay another two nights, we moved to the hotel literally across the street called The Haven. We had met a couple of families on the beach highly recommending the accommodations there. Boy were they right! We loved this place! We were actually lucky to even get in there and at such a reasonable rate. The rooms actually reminded me of the beach hotels in Greece. They were very white, bright, and crisp. The pool was almost that of a resort’s. It had nice beds to relax on (def. couldn’t do too much of that with a 3 year old running around), a bunch of floats for the kids, and was just all around really nice. The hotel also had a huge outside space with tables, bbqs, and a big fire pit in the middle. It was awesome for the kids staying there to run around and play with each other after the sun went down. We even roasted our own marshmallows the last evening there, which Grace absolutely loved (turns out she’s a pyro at heart).
Both of the places we stayed were about a 5 minute walk to a tiny, basically private beach. It was right on the Long Island Sound so the water was calm enough for the kids to play right on the shore without scaring the parents half to death. After dinner, we would head back down to catch the absolutely breath taking Montauk sunset. We were very happy with both accommodations and their locations, but will likely be booking The Haven for future family adventures.
As far as dining, we had both hit and misses. Our first night we went to Salivar’s. Grace had a very healthy meal consisting of edamame, french fries, pasta, and ice cream! LOL Sean and I shared a bunch of really delicious appetizers. This place had a huge menu, but we stuck to the sushi portion knowing you couldn’t get it any fresher. We enjoyed this place for sure. For our first breakfast we were just looking for a simple diner in town. If that’s what you’re looking for, you basically only have 2 options: Anthony’s Pancake House or John’s Pancake House. We ended up trying out Anthony’s. Wow were we stressed in that place. It’s not that it was even crazy busy, it was just SO disorganized. Maybe New York has worn down our patience. Also, the fact that Sean and I were in the industry for so long, we notice everything. It took forever to get sat, not because there weren’t tables, but because the man doing the seating was soooo slow. We had to beg for water and coffee several times and the food was super subpar-even for a diner. The next few days we opted for a place called Bliss. This place was simple, easy, and good. We got giant coffees and just had bagels and breakfast sandwiches, which we ordered from the counter. For us, simplicity is key. They had a nice back garden with chalk to decorate the patio with. That kept Grace contained for a bit while we enjoyed our breakfast. For lunch, we brought sandwich stuff with us so we basically just stuck to that. Grace pretty much just had an array of Goldfish, Popcorn, and Pretzels most lunches (You can send me my mother of the year award anytime THANKS). Our second dinner was at a place, also on the harbor, called Fletchers. The food and cocktails here were tasty. The scallops were probably the freshest I’ve ever had. Once again, Grace had pasta. If your kiddos are picky eaters, a lot of the menus at these seafood restaurants become pretty limited. I was happy with this place, but it’s not somewhere I would go again with a child. It’s more for a nice date night. The next evening we kept it easy and just picked up a pizza from Primavera Pizza. We set it up in the hotel’s garden and enjoyed a nice, chill dinner. The pizza here was really good. Again with the easy. Our final night we had dinner at Gosman’s Restaurant. This was the biggest MISS of our vacation. The food was absolutely disgusting. I’m not one to bash a place, but this place is worthy of it. Sean got the 2 lb. lobster. His excitement over it diminished as soon as he tasted how old it was. I ordered the fish and chips. Both the fish and the chips were frozen. Like why? You’re right there on the water…why in the world would you sell frozen fish at your restaurant? The madness of it all was how busy it was. It did have a gorgeous view of the harbor and the staff was nice enough, but it was an obvious tourist trap. I’d rather have edible food than a nice view. But hey, to each their own. Our biggest lesson learned was to bring our own food next trip. With a huge grill at the hotel and even the mini kitchen, it would be so much better to grab our own fresh fish or even some burgers and cook ourselves. When it comes to grilling, it’s really too delicious and easy not to do it, at least a few times on the trip. Spending a fortune on vacation just seems to come with the territory, but I really feel like we were kinda suckers when it came to the food. We just didn’t know any better. Anyway, ya live and ya learn!
On our third day, we drove out to the Montauk Point State Park. It had a cute playground where Grace could run around for a while. We walked down to the lighthouse, which was a sight to see for sure. We didn’t pay to go in. It’s something to do when Grace is a bit older. I had a feeling we would get in and she would be bored to tears. Instead, we walked down the path to the beach and skipped rocks for a while. Before leaving, we sat in the swings up top the overlook and stared into the never ending ocean. It was very peaceful. After, we ventured back into town, where we decided to stop by the Montauk Brewery. I would definitely recommend hitting this place up. You wouldn’t believe how cool it is. It’s literally run out of what looks like a barn house. They have a bar in front, with some tables and stuff outside. It’s very charming and the people working there do such a great job. The Watermelon Session Ale blew our mind. I never thought I would be into a beer with the word watermelon in it, but this one proved me wrong. Apparently, it is brewed as an IPA first, so as not too focus on the fruity side of it. This place had a really good ambiance about it. Was a favorite of the trip.
We peeked in a few of the stores in town to grab hats, t-shirts, koozies, and some beach toys. In fact, Grace ended up being a walking, talking billboard for the town of Montauk. We got a few basics at Plaza Surf and Sports. It’s a massive beach store with literally everything from clothes to surf board rentals. The best piece of clothing we go was from Montauk Clothing Company. Grace got this adorable shark hat there (posted in photo). We have a tough time getting her to wear hats in the sun and this was one she loved wearing. She wore it everywhere! And everywhere she wore it, she got loads of compliments. My favorite thing we bought in Montauk, was selfishly, a stand up paddle board rental. I had never done stand up paddle boarding before until our second day at the beach. I borrowed one from a fellow beach goer after asking how tough it really was to do it. I immediately fell in love! I had a tough time finding a place in the harbor that would rent paddle boards. I wanted to find somewhere close where I could just carry it to the beach so we didn’t have to face the hassle of tying it to the car. Our last day at the beach, I found Corey’s Wave. What an awesome business. They provide surfing lessons and rentals. They actually delivered the board to the beach we were at and picked it up when I called them to let them know I was finished. The board was nice, the couple that dropped and picked up really friendly, and the convenience of it all was incredible! With all of that, I couldn’t believe how reasonable the price was. I had such an amazing day on that board. Being able to paddle out in the ocean and just take it all on was completely exhilarating. I will definitely use Corey’s services for years to come.
Overall, this trip was one of the best we have had. Even with a couple of bad restaurant experiences, you lose all of that being at the beach. I guess that’s the whole point of going out there-letting go. Letting go of the city, letting go of the every day nonsense, letting go of all negativity… Being in a place like Montauk reminds you of the simple beauty in things and I cannot wait to get back.




  1. It’s really embarrassing, but we still haven’t made it to Montauk! I think we’ve always worried that it would be too crowded or too much of a party atmosphere, but your post makes it sound really approachable. Great tips, too. Will definitely look to do this sooner rather than later!

    Liked by 1 person

    1. Don’t be embarrassed! I had a good friend hook us up with the first hotel. If that hadn’t have happened we probably wouldn’t have gone either. I’d say it’s definitely better to go during the week. I’d be worried about the party atmosphere being a bit much over the weekends. Also, we didn’t want to drive at night, so we mostly just stayed close by our hotel in the harbor, which was super chill. Have a great time if you decide to venture out!


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