What Happens in Greenport stays in Greenport

Let me first begin this with, I survived!

Secondly, let me state I can never show my face in Greenport again – joking…Kinda

To say it was a fun weekend, would be a huge understatement.

Having never been to Greenport before, I had no idea what to expect. It is touted as the less prentenious, cheaper alternative of the Hamptons. They say it resembles a small New England town. It is the end of the line for the LIRR, but the gateway to Shelter Island.


All of that would be correct.

Getting out there is no small feat. With eight lanes of traffic, my cousin expertly maneuvered the car, while I covertly grabbed the “Oh shit” handle and prayed to the driving car Gods to get out of this Nascar rodeo.

All to soon thankfully, but perhaps not soon enough, my beating heart began to relax as the crazy darting traffic thinned and glimpses of countryside began to show, until suddenly it was all farm land and vineyards in the forefront, in the distance you could see boats bobbing along as they anchored in the marinas.


It was utter perfection to my mermaid heart.

The house we stayed at through AirBnB was the quintessential beach house. Only blocks away from the heart of town it was perfect, as we consummate New Yorkers could walk everywhere.

And walk we did.


That first night we explored boutiques, getting a taste of the shopping, food and drink. Taking pictures on the marina, that overlooked the stunning Shelter Island. We experienced the local revelry as only tourists can. Yet by the end of our weekend we had met enough people to feel like we had lived there all our lives. Or as my friends and I joked, just gone to Greenport High.

And what a place to live.


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