The Beach at the Cliffside Resort

In June Captain Awesome and I decided to head on out to Greenport, NY to get a little night away for our anniversary. It truly is a great destination for us because while there we get to indulge in some of our most favorite things… and beer! You see, Greenport is just a little over an hour away, and to make the trip go even better there are many Long Island wineries that we can visit. Once out there, Greenport is an adorable little town that has so much to offer. Restaurants, stores, bars, coffee shops and more. To me it is a quaint town that hasn’t blown up (yet) like the Hamptons, or even Montauk, but still feels like a destination. When there I felt away from it all, and isn’t that what makes a great getaway spot?

We planned the trip a little last minute and wasn’t sure on where to stay. We had only been to Greenport on a day trip and I just “googled” Greenport hotels. A few came up and the majority said they would only take a 2 night minimum stay, but we ended up at a beautiful spot. We stayed at the Cliffside Resort Condominiums. About a mile and a half out of town it was a peaceful spot with it’s own beach and pool. Each room is 2 bedrooms and 2 bathrooms, and immaculate. It had a small kitchen and a balcony and now that we know of this little spot we will be sure to return. Next time prepared with some food and drink to keep at the place.

As I mentioned above The Captain and I love to go to the wineries. As a matter of fact back when we were poor college graduates we would go out there as a date! Now, in Greenport there is a brewery too, so not only wine for me but beer for him.  Truly a perfect match! On this trip we visited the Kontokosta Winery . It truly is beautiful on a bluff on the sound. A new favorite spot we found on this trip was Mattebella Vineyards. It was such a beautiful spot. So much seating, they had servers and would be a perfect spot for a group outing. They offered some food as well as drinks, and we truly enjoyed it. Of course we visited both locations of Greenport Brewery. There is a tasting room in town, and one in Peconic. The one in Peconic has a great big outdoor area with corn hole and is just a great space to sit back and enjoy the beer.

There are so many places to choose from to eat in this cute little town. We asked a “local” at the Cliffside and were told to try out 1943 Pizza Bar for lunch. They didn’t disappoint! We got the coal fire pizza, and after looking at other people’s food we realized that we would’ve been happy ordering other things too! After lunch we made reservations at the Recommended American Beech. They have an amazing outdoor area which we saw on our last visit and we were not disappointed. I don’t usually rave about food but the burger I had there was amazing! Not to mention the Greenport Mule I had. Overall, it was the perfect dinner spot. In between lunch and dinner we met some friends at Claudio’s on the water for happy hour. I was bummed that we missed the live music, but it is always nice to have a drink on the water!

We traveled this time with out our kids, but I believe Greenport could be a family destination too. They have a beautiful carousel on the water, and with the town being on the sound with beaches nearby there is much to do with the kids.

I don’t feel like there are many resort towns on Long Island, but this is definitely one of them. It was a perfect getaway for me and Captain Awesome and we can’t wait to return.