Shelter Island jewels. (Photo by author)

Anyone who’s visited the beaches of Long Island knows how lovely they are. Over the years I’ve clocked time in the gorgeous towns of East and South Hampton, the hamlet of Amagansett, and one of my favorite places in the world, Montauk, affectionately known as The End. But in all that time, I’d never been to Shelter Island. Always passed on the way out to the eastern end of Long Island, I’d look at the ferry sign and think that one day I’d visit. Anyone I know who’s been always spoke of how gorgeous it is. This past weekend I got to see its beauty.

I’m leaving on a…quick ferry ride. (Photo credit: Tim Kelly)

Nestled between the North and South Forks of Long Island, the island really is sheltered. I was heading there for a wedding, and took the first morning train on the Long Island Railroad out to Greenport. The three-hour journey is the first step in getting that “away” feeling and gives you time to read, nap, or catch up on whatever needs catching up. By the time the train arrives, decompression is nicely underway. A few steps later you’re at the ferry, excited with the anticipation of being so close to your destination. It’s a quick seven-minute zip across Shelter Island Sound but enough time to make me feel like I was a million miles from New York City.
Visiting Shelter Island is like being in a time capsule. With its lack of noise and overall hustle and bustle, white picket fences, gabled homes, wrap around porches, rolling hills, boats bobbing in the harbor, and lush land, it feels like Mayberry RFD. Its natural beauty is startling. Just to give you an idea, The Nature Conservancy owns one-third of the island. This keeps it real and keeps it wild. No one was walking around with head’s down staring at their cell phone; in fact I didn’t see one person on their phone the entire time I was there.

Dering Harbor.

There’s no such thing as perfect but to this visitor the pristine beauty of Shelter Island was almost overwhelming. To boot, the weather was bright sunshine, no humidity and clear skies. From the moment I checked into the Chequit Inn, the wedding couple spoiled me (and all their other guests) rotten with goodies and meals. Sure, I was there to celebrate their union but being there gave me—and the rest of the crowd—an opportunity for a little vacation. A mode that everyone seemed to take to immediately.

The added bonus was reuniting with friends who don’t live in the US anymore, and making new ones. A gang of us rented bikes and spent Saturday exploring. It’s probably the best way to see Shelter Island, you can stop and start back up when you like. We rolled through the roads of Dering Harbor and gaped at the off the hook homes that look like something out of The Great Gatsby. We made a pit stop on a wide-arced, sandy white beach, empty except for a sole person in a deck chair reading; a turquoise umbrella sheltered her. Aside from the gentle lapping of water on the shoreline, all was quiet. She had the world at her feet and heaven around her.

A sweet ride.

We swam in Coecles Harbor, near the Ram’s Head Inn, where I found my new favorite sport—paddle boarding. We could have lolled seaside all day but we had to head back to our hotel to get spiffed up for the night’s festivities. Cycling home along the shoreline the breeze carried the sweet smell of grass and clover mixed with salty air, creating the sort of moment that only summer can bring. The sort of feeling you had as kid, when you didn’t have a care in the world. When a minute seemed like an hour, and before sound became noise. The feeling that you didn’t want the day to end, wishing you could capture it forever. Magic.

Sunset ceremony sky over Coecles Harbor. (Photo credit: Lawrence J. Winston)

We returned to the Ram’s Head for the outdoor wedding ceremony during that golden hour where the sun blazed over the rolling lawn that overlooks the harbor. As it set, it cast a lingering gift of neon orange glow over the dinner party. Then this brilliant fireball slowly dipped into the sea. Delicious food, good times, no one wanted the glamorous night to end but we eventually had to call it quits.

Show me to my table. (Photo credit: D. Powell)

The following day the celebration continued with lunch on a secluded private beach. More food, more drink, more laughs, more swimming. We combed for seashells and found a treasure of mermaid’s toenails, scallop, spindle and snail shells. My sun hat became a bucket for my bounty. So many shells, so much sunshine, so much summer.

Someone asked me what time I was leaving, I said never.