What To Do When You’re Out In The Hamptons

Being in New York City definitely has its perks. Like being only 2 hours away from the Hamptons and Montauk.

The first time I went to the Hamptons was when Allie invited me to come spend a weekend at her house. It was a weekend to remember FOR SURE. I think that was in 2016. Since then, we’ve had so many fun trips out East together – from poolside chats, to long dinners out at restaurants, to shooting summer and fall content in town, to late nights that I’ll never forget (although Allie might want to hehehe), to venturing to the North Fork for the morning to shoot in lavender fields – we’ve done it all.

Fast forward to this year: Nick teaches yoga some weekends at a gorgeous hotel in Montauk, so we’ve spent some weekends out there. Naturally, not much was open and things are definitely different. But now, heading out East is a great little weekend getaway for us.

where to stay

The only place I’ve actually stayed in out East is the Marram in Montauk  because Allie graciously invites me to stay at her house. Marram was completely renovated last year, and honestly one of the most gorgeous places I’ve stayed. It’s situated RIGHT on the beach. It’s such a calming atmosphere, with neutral vibes, and just such a great place to stay. Since COVID, they’ve had to come up with creative ways to do things, but now that New York is in a good place, more and more things are starting to open (with restrictions and cautions, of course). The pool is open, the fire pits/lounge areas outside are open, and they have a service that sets up beach chairs/umbrellas for you just steps outside of your room! They also have yoga and meditation – not in person yet, but all over Instagram Live – so guests can still experience some kind of wellness during their stay.

Some other hotels include

what to do

Sunset at Wolffer Estate (Winestand) Sunsets at Wolffer might be one of my favorite things to do in the Hamptons. I recommend getting there earlier than normal to get a table. But the only thing to do next is grab a bottle (or two) of your favorite wine, and enjoy! It’s such a relaxing atmosphere, and one of the best sunset spots out East!

Hang at Ditch Plains I’m not a surfer at all. But there’s something so cool about hanging on Ditch Plains beach watching people surf.

Get a drink at Montauk Beach House Nick brought me to his favorite spot in Montauk and we go there every time we’re out there. It’s probably my favorite place in Montauk. I love how you can go in the pool, grab a drink and lay down on one of their chaises, or sit around fire pit tables.

Walk around Southampton In my opinion, Southampton is one of my favorite towns in the Hamptons. Shopping aside (obviously it’s great), I just think it’s so cute. And they have lots of places to get little snacks and treats (I love fudge). In the next part of this post, you’ll see one of my favorite restaurants is in Southampton!

Visit local farm stands I always love in the Hamptons, and seeing all of the little farm stands with fresh fruits and veggies. It’s a great way to support local businesses. Some stands that come to mind are Balsam Farms and Serene Green.

where to eat

Some of my favorite restaurants are out East. No, it’s not cheap to go out to eat in the Hamptons, but there’s nothing better than wining and dining when you’re out there for a weekend.

Moby’s Moby’s is honestly, like, a staple in me and Allie’s Hamptons diet. I think we make sure to go every time we’re there…even if it’s a 5PM dinner reservation LOL. I mean, I get the exact same thing when I go: Tuna Crudo, Burrata, and the Spaghettini. *chef’s kiss*

Tutto il Giorno This is my second favorite restaurant. Actually, it ties for first with Moby’s. I think the last time Allie and I went there the waiter judged us for ordering SO much food. It was fantastic.

Topping Rose House Dinner at Topping Rose House is always a solid choice. I love their wine list, and the food is always good. The only thing I will say, that sometimes it feels like people are slightly entitled at this restaurant. I don’t know why I feel these vibes when I’m there. But nonetheless, still have always had a good time at dinner when I’ve gone.

Lunch Summers are for lobster rolls. I don’t think there’s been a time when I’ve been out East and didn’t go to Lunch for a lobster roll.

Almond While I definitely prefer Almond in Flatiron, I do like doing drinks at Almond. Their dirty martinis are DELICIOUS.

where to go out

Naturally, the Hamptons are known for it’s party scene. So here’s some bars/places I love to go to have a good time.


Crow’s Nest

Sloppy Tuna (which is now Nick’s on the Beach)

Stephen’s Talkhouse


what to wear

Obviously when you think of the Hamptons, you think of luxury. So naturally, many people wear their best looks. But to be honest, I usually wear my most comfortable, casual, yet still put together looks. So basically, I wear what I always wear. I don’t LOVE getting dressed up when we go out, I actually feel like the vibes are way more chill out there.

Here’s what’s always on my packing list (also remember it gets sliiiightly chillier at night):

  • Jeans
  • Oversized t-shirts
  • Sweatshirt
  • Long sleeve tee
  • Birkenstocks
  • Mules
  • Heeled sandals
  • Going out blouse
  • Bathing suit
  • Denim shorts
  • Big tote
  • Crossbody

Many of my Hamptons looks are linked in the LTK app.

photos by allie provost

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  1. 7.13.20
    Lisa Autumn said:

    This look is so summer casual and I love it!

    Lisa | lisaautumn.com

  2. 7.13.20
    Laura Leigh said:

    I want to go SO BADLY! Definitely very high on my travel wish list! I always love following y’all’s stories while you are there. LOVE this outfit. LOVE this spot. LOVE those hydrangeas.

    xo Laura Leigh

    • 7.14.20

      YES YES YES, you HAVE TO! And I know you love the hydrangeas 😉

  3. 7.14.20

    Love your outfit! And thanks for all of the tips for the Hamptons. I’ve been wanting to go for awhile and I think we may have to take a trip there next summer!

    xx Chelsea Finn

    • 7.14.20

      Thank you, Chelsea! You HAVE to take a trip – it’s so gorgeous out there!

  4. 7.14.20
    Morgan said:

    Yep, for sure saving this post for when I finally get to head to the Hamptons one day! It always looks like you have the best time there!

    the HER chronicles [] http://theherchronicles.com

  5. 7.14.20
    Jenn Lake said:

    Dana! I’m LOVING this lewk on you!!!

  6. 7.14.20

    I am obsessed with your outfit! I love those loose pants and the colorful scarf.