A weekend at The Pridwin Hotel & Cottages on Shelter Island felt like the kind of escape Jason and I didn’t realize we needed until we were there. From the moment we arrived, everything slowed down in the best way. The setting is classic and charming, right on the water, but with all the thoughtful touches that make it feel elevated and special. It was the perfect mix of relaxed and refined—exactly how we love to travel together.
Moke
One of our favorite perks was the complimentary Moke rental, which made exploring the island feel fun and effortless. Cruising around Shelter Island with the windows open, salty air blowing in, and nowhere to rush to was such a highlight. It instantly set the tone for the weekend—easy, playful, and a little nostalgic, like summer vacations should feel.
The experience was taken to another level with a private sunset boat ride, complete with champagne and lobster rolls. Watching the sun dip below the horizon while sipping bubbles and sharing lobster rolls felt incredibly intimate and memorable. It was one of those moments that makes you pause and think, this is exactly where we’re supposed to be right now.
Back at the hotel, we enjoyed dinner at The Pridwin’s restaurant, which focuses on seasonal ingredients and elevated coastal flavors. The atmosphere was warm and inviting, perfect for lingering over a meal and a glass of wine. Everything felt thoughtful and unpretentious—great food without the fuss, which we always appreciate.
We ended one evening at Sunset Beach, soaking in golden-hour views and that unmistakable Shelter Island energy. It was the perfect contrast to the quiet elegance of The Pridwin—lively, beautiful, and full of summer buzz. That balance of serenity and fun is what made this getaway so special. Our stay at The Pridwin was romantic, refreshing, and truly unforgettable—one we’re already talking about returning to.
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