My mom and I booked a last-minute trip to Shelter Island to celebrate my birthday and it could not have been more perfect! It was our first time there and we absolutely loved it. We stayed at The Chequit, which is nicely nestled in the Shelter Island Heights area and is walking distance from shops, restaurants and the harbor. The hotel was recently renovated and every detail was accounted for—every room even comes with a sun hat and a turkish towel!
Shelter Island is only accessible via ferry—either to the North Fork of Long Island or to Sag Harbor. It was a bit overcast one day so we ventured over to Sag Harbor for the afternoon. It's such a picturesque town with great shops to wander through. Back on Shelter Island, we loved going to the beach near the Sunset Beach Hotel, which is another great place to stay or spend some time at.