Travel Guide: Southampton, NY

IMG_0641Hey everyone! I recently got back from a trip out to Southampton for my friend Natasha’s birthday! Since seeing it on Gossip Girl and hearing about how boujie it is, my gal friends and I had been wanting to go for years! It was in a lot of ways exactly what we thought it would be like in the sense that there’s a lot of upper class people and people are driving luxury cars like Porsche’s and Bentley’s on every corner. A lot of our friends gave us advice that when people go to the Hamptons, they typically rent a house and stay in that house to party (rather than going out to a lot of different places). Since we don’t live near NY, we wanted to do a lot of exploring while we were out there and I wanted to share that with you guys!


Where We Stayed

We stayed at an Airbnb 5 minutes from the Southampton train station (I can’t find the Airbnb link 😦 but the address was 130 Powell Ave). It was a close driving distance to a lot of restaurants and shops which was nice! Unfortunately our house didn’t have a pool but was much more affordable than other houses in the area.

How We Got There

My friends and I all got to Southampton a different way lol.

  • I flew in the night before to JFK so that I could spend a morning in NYC before taking the train to Southampton from Penn Station (~$20 one way).
  • Natasha flew directly into the ISP airport on Long Island and from there had the option of 1) taking an uber (~$50) or 2) taking an uber to the Patchogue train station and then taking an hour train to the Southampton train station. She ended up doing option 2 which was cheaper but I’m not sure what the exact price was.
  • Megan flew to JFK and then took the Hampton Jitney bus to Southampton (~$35).

How we got around

Guys we originally tried to rough it and just uber around but the Hamptons are not built for roughin’ it. Lol There are no sidewalks anywhere around the houses or restaurants because everyone drives. So after a day and a half we went to Enterprise and got a car since that was way more convenient and cheaper than taking ubers the whole weekend.

Where we ate

RUMBA Inspired Island Cuisine & Rum Bar– This place was affordable ($$ restaurant), yummy, and on the water! We loved the duck empanadas, shrimp tacos, fries, and sangria! The bar was lively too and there was a cool party-looking-bus at the back of the restaurant.

Cowfish Hampton Bays– This restaurant was also on the water and was one of my favorites! I ordered the clam chowder and it was a generous portion, house favorite, and so good! The lobster rolls here are $32 which is STEEP so I recommend splitting it with a friend since it’s plenty big (and comes with fries). We all paired our meal with a beer from Montauk Brewing Company! Once we were done eating, we sat on the couches at the front of the restaurant. It was so nice to chat and just watch the boats in the bay.

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Wölffer Estate Vineyard– Wölffer is a vineyard that my friend introduced to me about a year ago. I had been dying to go here because they seem so unique and their packaging is incredible. They are well known for their rosé and their rosé cider- both of which I definitely recommend! We were also told that Justin Bieber typically visits this vineyard when he’s at the Hamptons.Processed with VSCO with hb2 preset

Tate’s Bake Shop– Omg this place was amazing. I was obsessed with their chocolate chip cookies and cream cheese brownie (literally like a cheesecake and brownie combined). My friend said you can find their signature chocolate chip cookies in Whole Foods too so I’m definitely going to search for them.IMG_1438

Where We Went Out

Southampton Social Club– This spot had a $20 cover but was a great spot to stay at the whole night. They had a big outdoor patio with a bar as well as an indoor bar. Once it got later in the night, the dining area became a dance floor and was really fun!

We were also told that Beach Bar in Hampton Bays was fun but we didn’t go experience it. We also heard that Montauk is super fun for going out so if we go back to Long Island we’re definitely planning to live/ go out in Montauk.

What We Did

Adventure Paddle Board and Yoga Such a unique experience for just $35! It’s so funny to watch your friends fall off of a paddleboard if it happens during the yoga class (one of our friends did). The yoga class was well taught and was great to experience on the water. The instructor also let us paddleboard for however long we wanted after the class so it was like paying for two things with the price of one!

Sag Harbor– This was the cutest area with tons of boutiques, restaurants, and ice cream spots. We also walked down to the water to see the windmill and boats.

Cooper’s Beach– Note: this beach charges a $50 parking fee from 10am-6pm. I really enjoyed being at this beach though in the early evening. The water was freezing but the beach itself was nice.


Hope you all found this post helpful! Leave any recommendations in the comments!
❤ Emily


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