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Weekend Get-away: The Chequit, Shelter Island

by Marissa on September 2, 2015

The Chequit Shelter Island - Where I Need to Be

Like lots of things during summer, my blogging has gone on a bit of hiatus. But I’m back for a minute to rave about our long weekend surprise trip to Shelter Island where we stayed at The Chequit Shelter Island. This trip came just as Summer seemed to settle into New England and we were greeted with the most perfect weather. 

Every Summer we spend at least one weekend out East, but it’s usually in The Hamptons. When we visited Shelter Island for the first time two years ago, we knew we had to go back. It’s the perfect blend of laid back-casual meets city-chic at the beach. Since it’s an island, the only way to reach it is by ferry so that makes it feel slightly more chill and secluded than dealing with the crowds at the beaches in Montauk or The Hamptons. 

We left Thursday afternoon, but the rain and traffic prolonged our travel time so that by the time we arrived, we were both ready to relax.

The Chequit Shelter Island is a charming Summer cottage-turned Inn that sits on a hill. Newly opened and renovated with a beachy-antiquey feel, it’s one of the most inviting places to stay on the island. When we checked in, we were shown to a cozy room in the annex which is a separate building but a stone’s throw from the main cottage. We quickly changed and went to the on site restaurant Red Maple for dinner where we had some of the most delicious food of the trip. The focus at Red Maple is on local and seasonal and David’s chicken and my larger-than-life prawns did not disappoint.

The Chequit Shelter Island - porch plants - Where I Need to Be

After an early bedtime and an early-morning run around the island, we made our way to the porch for an out-of-this world, healthy, homemade continental breakfast. This was not cereal and toast. We’re talking a daily frittata, homemade granola, Greek yogurt, fresh berries and homemade pastries. The best part is that is was included with the room.

The Chequit Shelter Island - grounds - Where I Need to Be

We always lingered a little longer at breakfast because of how inviting the porch and the grounds were for eating and relaxing. 

The Chequit Shelter Island - lobster roll - Where I Need to Be

The rest of the trip was spent exploring the nearby towns: lunch in Sag Harbor, a day trip to Montauk and pit stops for green juice and lobster rolls on Montauk Highway (I’m all about the balance!).

The Chequit Shelter Island - beach at sunset - Where I Need to Be

Of course, a trip to Shelter Island isn’t complete without sunset drinks at Sunset Beach. We made sure to sneak that in too!

Another favorite meals was at Vine Street Cafe, a must-visit on Shelter Island. It was impromptu and we were lucky to snag a seat at the bar where we dined on delectable grilled octopus, a tasty arugula and olive salad and a cheese plate along with local rose. 

On our way home Sunday evening, we stopped at a few of the road side farm stands to pick up local fruit and veggies which are always super fresh and so good. 

It was truly one of the best and romantic trips I’ve had and the best part is that it’s only a couple-hours drive from the city. 

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