I went to the Hamptons with a family that has been going every summer for over 30 years. I got to experience this popular destination through the lens of (sorta) locals. And honestly, by day two, they sort of quietly rewired my brain on the whole place for me, and in the best way.
I visited out east when I very first moved to NYC. It was a really quick trip but we truly packed it in. We saw so much in 36 hours. However, I remember thinking after that trip that I didn’t really feel the need to go back again. I felt like I saw quite a bit of it (we literally stopped into three of the most popular towns) and I just didn’t love the vibe enough to want to go back again and again. All that has now changed.
I’m actually not surprised by this. My first trip to the Hamptons had mediocre food outside of an incredible lobster roll that was nowhere near any town you see on TikTok. And on this particular visit, the hosts firmly admitted “the food here isn’t that great”. It’s not bad…it’s just, not that great.
There are some gems for sure and our hosts for the weekend took us to incredible meals that I absolutely loved. I suppose you just need to know where to go and there can be a lot of trial and error. Not everything you see on TikTok in viral roundups may actually be all that great.
I also find it fascinating that there are several popular New York City restaurants that also have locations in the Hamptons like Saint Ambreous and Le Bilboquet. Personally, when I visit somewhere new, I kind of want to also eat at new places. It blows my mind that New Yorkers, who have every cuisine and thousands of restaurants at their fingertips, would be excited to make a reservation at Saint Ambreous, the Hamptons location.
A few really good meals we had included the lobster tacos at Gosman’s, a company that supplies most of the seafood to restaurants in the Hamptons. And also Moby’s, a great Italian spot. Which says a lot because I’m a bit of an Italian food snob if I’m being honest.
This may be a combination of the stage of life I’m in—late 30s, not really drinking, friends are starting to have kids and so on. But a slower life of easy mornings, beach walks, casual lunches at home and simple dinners is really what this destination is for. I’m sure there’s partying at The Surf Lodge and other popular bars, but if you’re not into partying, this really is the best spot for a little relaxation.
I’ve now experienced both a hotel and a house and can confidently say, a house is the way to go. This is especially true if you don’t really want to eat every single meal out, which we didn’t. Instead, we could enjoy a full kitchen to whip up some eggs along with all the fresh fruit and produce from the farm stands. Lie by the pool or hop into town for some shopping, before diving into all of our prepared foods we stocked up on at Round Swamp Farm for lunch and afternoon snacking.
Having a car is also key because everything is so spread out. Something I was so surprised by in my first trip out east. You will either spend a fortune on Uber or you’ll be stuck in the one town you’re staying near. Our house was a quick 5 minute drive to some great coffee shops for early morning coffee runs, but each town is easily a 20 to 30 minute drive between them. If you want to shop and explore them, you’ll definitely need a car.
Listen, New York has definitely rewired my brain some when it comes to prices. It’s astronomical. But the Hamptons are possibly even worse. Everything is just so pricey for a few reasons. This destination is seasonal, so businesses want to maximize the season as best they can. The product is usually locally sourced from all the amazing produce. And it’s New York!
Just prepare yourself for this, because I don’t think there’s really any getting around it unless you cook most of your meals at home. Again, another perk to having the house so you can at least do easy breakfasts and lunches, or have a fun BBQ at home one night instead of going out to an expensive dinner.
I don’t think I truly understood this on my first visit. I remember stopping at Round Swamp Farm at 4:30 in the afternoon when the shelves were picked over. We didn’t need a meal, so we just got some cookies to try. They were good, but expensive.
But this time, since we spent so much time at the house, the produce was truly the luxury of the whole weekend. Incredible berries and peaches to start the day with. All the prepared foods from the different farm stands like yes, the all-too-popular Round Swamp chicken tenders (they’re good, but they’re $25) and a raspberry cream pie from Briermere Farms that was our post-dinner sweet treat every night.
Getting to enjoy all of this incredible food was one of my favorite parts of the whole trip. Especially as someone who hates spending a ton of money at restaurants, fancy meals are just not my thing. But casual snacking at home with good food? That’s my vibe.
After 5 days in the Hamptons with locals, I can confidently say that there’s definitely a right way to do it. One that takes advantage of the slower pace of life, enjoying the best produce, and also just knowing to suck it up when it comes to prices. It’s a vacation after all, right? If I ever go back, I’d make sure I do a few things:
Have a car and a house - I’d opt for a hotel with a pool and beach access if it’s a short trip
Definitely stop at Briermere Farms for raspberry pie to enjoy as a sweet treat throughout your weekend
Have a lot of meals at home when possible; the produce really is incredible
Choose only the best spots for dinners and make reservations ahead of time
Go on beach walks. This was the highlight of both my trips out east.
I created a comprehensive guide to the Hamptons from how to get out there, where to stay, a breakdown of the towns and more. I’ve also included my favorite restaurants and shops over on the blog. Read the full guide below.
xx Jessica
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