Our First Family Trip as Four: Montauk in November

When I learned that my brother and sister-in-law were getting married in Tarrytown / Sleepy Hollow, NY—and that I’d be about eight weeks postpartum on their wedding day, I knew the only way to avoid complete chaos while traveling with two (virtually) under two was to extend the trip.

As much as I loved taking Charlie to Manhattan when she was one, I remembered the reality: navigating the city in cold weather, hauling a car seat, stroller, and bags through narrow hotel hallways… it was a lot. And Manhattan hotel rooms? Not exactly designed for two adults, a toddler, an infant, and all the gear that comes with them.

So Manhattan was out. But where to?

I started my manifestation list: fun, effortless, and bucket-list material. Somewhere new that offered space, waterfront views, seafood, walkability, and warm hospitality for a family of four.

That’s when I landed on the idea of our first family vacation as four, in the Hamptons.

Why Montauk

In my research, Montauk checked every box. The downtown looked charming and easily walkable. The surfer culture gave it a laid-back yet elevated energy, not as fancy as East Hampton, but not as sleepy as Amagansett. We could fly into LGA, rent a car, and be in Montauk in under two and a half hours. (When you have two tiny travelers, proximity is everything.)

We spent five nights in Montauk in November 2025, and everything that follows is what I learned, loved, and would’ve loved to do if it were in-season—or if this had been more of an adults-only trip instead of a “brand-new baby” kind of trip.

So, would I go back? Absolutely. In fact, Ronnie’s already talking about heading back in July for tuna season.

Alright, let’s get into it.

Getting There

This was our first trip to the Hamptons, and we went during what’s definitely considered the off-season. From my research, many of the most-recommended local spots close after Labor Day. So if you’re hoping for that “summer in the Hamptons” energy, you won’t quite find it in November. What you will find, though, is a version of the Hamptons that’s easier to get to, blissfully uncrowded, and, despite its sleepiness, absolutely charming and delightful, honestly, maybe with even better hospitality.

We flew into LGA since we were renting a car and wanted an airport that was central to both Montauk and Tarrytown, LGA sits right between the two, so it worked perfectly. We did briefly consider flying into MacArthur, but ultimately decided against it.

The drive was about 2.5 hours each way, though a long stretch of the route runs along Highway 27, one lane in each direction, with speed limits that dip between 45 MPH and 25 MPH. I can only imagine how backed up it gets during peak summer weekends (especially if someone’s trying to make a left turn through traffic). It reminded me so much of driving from O’Hare or the western suburbs of Chicago to New Buffalo, Michigan… about the same distance and level of commitment. Two and a half hours feels doable… until you hit that extra hour or two of traffic. Still, the payoff is so worth it.

If you’re visiting in summer, I’d highly recommend traveling early in the morning or late at night to avoid congestion.

One thing that surprised us: the deer population. We saw a road sign noting nearly 600 deer-related accidents on Highway 27 in the past year—and honestly, I believe it. We spotted so many deer families (including one majestic buck!) along the way.

For this reason, and for sheer convenience, I finally understand why Blade exists. If you want to splurge, you can book a Blade helicopter directly from LGA to the Hamptons and arrive in a fraction of the time.

Eat

I am sure there are a gagillion incredible eateries that I’ve missed, but what I have included were our favorite stops while we were there. Worth noting, since it was off-season, and we were traveling with two kiddos, we didn’t get out as much for dinner as we would have otherwise, regardless, these are the spots we loved:

Montauk
- Harvest — We ordered for carryout on our first night in town, based on a recommendation from a friend. The Fluke, Short Rib, and Burger were very good. The restaurant was also super cute.
- Gigi’s at Gurney’s — We ended up eating here twice during our stay because it was so close and so good. For our anniversary dinner, Ronnie and I snuck away from the kids for a dozen oysters, the angry lobster, a delicious branzino, and a 20oz ribeye with Angry Lobster. For lunch a few days later we tried the Lobster Roll, Burger and the Beer Battered Onion Rings … I am still dreaming about the Beer Battered Onion Rings.
- Montauk Bake Shoppe — My friend Carolyn told me about this spot, and said that I couldn’t leave Montauk without trying the Jelly (or Cream!) Stuffed Croissants, after trying them myself, I can confirm they are indeed worth going out of your way for. Tasha, my bestie, joined us a few days into our vacation, and as she will attest, I took her back for these.
- The Dock — Okay, OMFG, do not miss this place. First, the decor is hilarious and slightly offensive, but it’s a good vibe. Secondly, we had the Lobster Grilled Cheese, Almond Crusted Flounder, Crispy Halibut Tacos, Fresh Tuna Melt Sandwich, and Shrimp Chowder and I can’t say enough good things about any of these items, we were BLOWN away by how good the Flounder was, how unexpectedly delightful the Tuna Sandwich was (our waitress recommended), by how much damn lobster was on the grilled cheese, and finally whatever sauce came with the tacos actually blew our mind.
- Joni’s — I loved this cute little breakfast nook. It was the most bumping spot in town on Sunday morning, so naturally I returned a few days later to check out the hype for myself, after my delish breakfast burrito, and acai bowl, while watching sunrise over the ocean less than a block away, I can say this: I get they hype. It’s a great spot! Apparently Joni is a local legend, she’s got a Montauk cookbook, so I went ahead and snapped a pic of a recipe that looked quite fabulous to try at home.
- These spots we unfortunately didn’t get a chance to go to because they were closed for the season, but came highly recommended by locals:
  - SíSí — Mediterranean inspired menu, waterfront dining.
  - Duryea’s — The Lobster Cobb is legendary.
  - Inlet Seafood — Apparently a great spot for sunsets and casual(ish) bites
  - Gosman’s Dockside — Supposedly one of the best spots in town if you’re craving a seafood lunch!
East Hampton
- Tutto Cafe — During a mid-afternoon shop and putz around East Hampton, we needed a caffeine pick-me-up, this was our spot. So cute, reminded me of a little Italian cafe. Great coffee, great desserts, very European service.
- Smoky Buns — THIS BURGER THOUGH. Oh my god, we really enjoyed our lunch at Smoky Buns, pretty much the entire group got the Smash Burger and the Hot Honey Chicken Sammy. You can’t go wrong either way. Good googly moogly.
- Citarella Market — I LOVE a shoppy shop and Citarella did not dissapoint! An incredible selection of fresh produce, curated prepared foods, and the cutest brands! One of my new brand discoveries was Xilli, “a collection of thoroughly-researched, artisanal Mexican preparations, that represents our country’s true culinary heritage, while honoring its traditions” … I got the oaxacan salt which I can’t wait to use as the salt rim the next time I make a spicy mezcal marg!
- Grindstone — The Spicy Mocha!!! The Peppermint Mocha!!! The DONUTS! This spot was a highlight and became my “daily coffee run” spot while we were in town (aka I went their 3x).
Amagansett
- We had a reservation at Rosie’s but when the girls were too tired to make it, we opted to stay home instead.
- Bonfire Coffee House — Yum! My mom and I spent an afternoon here (the croissant sandwich was SO good) when it was rainy and we were on girl duty, with nowhere to go. The hospitality was the biggest highlight, what a wonderful group of women running this spot!

Stay

Airbnb — We opted to stay at this Airbnb because we needed space to spread out and we were traveling with a group of peeps: me, Ronnie, our daughters, my parents, and my bestie, Tasha. It was 5 min walk to Gurneys, 10 min drive to downtown Montauk, and a 15 min drive to East Hampton. Complete with pool, hot tub, and a huge kitchen perfect for making the Fish Tacos of our dreams (after Ronnie and my dad caught 18 striped bass and took home the maximum amount of fish meat, 20lbs, they could fathom) we ended up making fish so many different ways — Sashimi, Baked, Grilled, Tacos, you name it!
Gurneys — If Ronnie and I were going for an anniversary trip without the kids, we’d probably stay here. It’s bougie, but the hospitality is incomparable, the resort is sprawling, the restaurants and spa are excellent, it’s right on the beach, and they have indoor (including hot tubs and cold plunge) and outdoor pools that you only dream about!
Hero Beach Club, Marram and The Surf Lodge are spots we discovered while in Montauk, each had a charm about them that made me think “maybe I’d stay there at some point” they are more affordable than Gurneys, but have a wonderful surfer-aesthetic and vibe to them I really like.

Workout

At eight weeks post-partum, traveling to the Hamptons in the off-season, I wasn’t sure if I was going to feel like going to a group fitness class, but if I did, these are the spots I would have checked out:

New York Pilates — I’ve never been, but this looks like the spot for THAT girl in Montauk and East Hampton.
Soul Cycle — After the original Soul Cycle opened in Manhattan, they opened a spot for Hamptons-going summer people, I feel like going to a Soul Cycle class in the Hamptons pays homage to the co-founders and the cult that is SC.
Tracy Anderson — I have never been to one of her classes or studios, but she’s got two it looks like in the Hamptons, considering how many people are obsessed with her, I would certainly check one of these out.

Play

Depending on what you’re into, I think the Hamptons really offer so much to do! With a five day itinerary, I’d probably do a combination of these things!

Shopping Day — Get in the car and go shopping at the various stores along highway 27 or in the downtowns of Montauk, Amangasset and East Hampton, here were a few of my favs: Homeport (Montauk); TWP, Clic Home (East Hampton)
Spa Day — Head to Seawater Spa at Gurneys for a Spa day! I had a fabulous massage and enjoyed the spa amenities and ocean view at the indoor pools and tubs after.
Fishing Charter Day — Despite my desire to go fishing with Ronnie, with my mom and dad in town, and my dad, ever the fisherman, I had him accompany Ronnie on a charter on My Joyce for some fishing. They went out for “Striper” and holy shit did the fishing gods deliver, after catching 18 Stripers (you can only keep four), the boys came home smiling ear to ear. Shout out to Mark at Pelagic Outfitters for hooking this up.
Adventure Day — We passed a good amount of signs for Wine Country, and while I can’t quite say that we “found it” we did drive from Montauk to downtown Sag Harbor passing Wolffer Estate on the way. And even took take the Ferry to Shelter Island. This was a fun little exploration, and had we had more time (and no kiddos with us) I think we would have really enjoyed adventuring quite a bit to the other spots nearby.

The Final Verdict

When I originally planned this vacation, Ronnie rolled his eyes “do we really want to go to The Hamptons in the off-season? What are we even going to do?” I insisted, and he, begrudgingly, went along with my plan. I knew if I could just get him there, he’d see what all the fuss was about, and that the off-season would actually be the PERFECT time to go for our first trip there, as it would make exploring 100x easier, and allow us to map out our favorite spots, assuming one day, we’d want to do a return trip.

So where did we net out? Ronnie and I can’t wait to go back.

Ronnie is already planning a trip back in July for Tuna season. This trip also inspired us to think about other destinations on the East Coast that we would love to check out, which offer similar amenities and vibes, including: