Real World/Road Rules Challenge: The Hamptons

hamptons15After months of anticipation, it was time to stop being polite and start heading to Southampton, New York for my first vacation of the summer. I was especially excited because this was my first time in the Hamptons. Dave and I rented a place from AirBnB with some of our college buddies and 7+ strangers. I have to give major kudos to my friend Tom for organizing the booking of the place, picking up the food, and putting together a great crowd of people. The area itself is beautiful with lush, hydrangea lined homes and beautiful beaches. I think we all have an afterglow of sorts; it was a truly amazing weekend.

Dave and I traveled from Boston to New London, Connecticut and caught the ferry to Orient. From there, we drove a little bit and caught the ferry to Shelter Island. The final ferry from Shelter Island took us to Sag Harbor, and from there we explored a bit until check in time.

hamptons2The best non fried fish tacos from Estia’s Kitchen in Sag Harbor.


hamptons3All of the bacon and eggs á la Ron Swanson.


hamptons4As a responsible adult, I purchased $50 worth of super soakers. They were heavily utilized.

hamptons5 hamptons6 Special delivery to the beach.

hamptons7Dave, Matt, and I cooked up a massive taco feast. The entire weekend in general involved mass consumption of tacos and rosè.

hamptons8 hamptons9 hamptons10 hamptons11On Saturday the group ventured to Montauk. Dave and I visited the Montauk Point Lighthouse and climbed the cliffs (which was super scary). I had “Play Crack the Sky,” by Brand New stuck in my head the entire time.


hamptons12Some of the group practicing their performance to “End of Time” by Beyonce.

hamptons13 My friend is an educator at Amber Waves Farm in Amagansett. He moved to East Hampton in June and suggested that Dave and I visit. Amber Waves began as a wheat farm but there are lots of other goodies. We had actually passed it on our way to a family friend’s house on Friday.

hamptons14 Raspberry bushes.

hamptons15 Hi!

hamptons16 Even more amazing fish tacos (+ beef empanadas) from Maria’s Kitchen on Shelter Island.

hamptons17 Shelter Island Craft Brewery’s summer shandy.

hamptons18Almost home on the big ferry.

12 thoughts on “Real World/Road Rules Challenge: The Hamptons

  1. Rena

    Unfortunately I have never been to the Hamptons but your beautiful post show me again that this place is really worth to visit! Really kudos to your friend – and to you, too, that you share here the amazing pictures <3
    xx from Bavaria/Germany, Rena


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