Stories/ A Travel Guide to Shelter Island by Jillian Eversole

A Travel Guide to Shelter Island by Jillian Eversole

Why The Pridwin Is the Only Place to Stay on Shelter Island

Shelter Island surprised me at every turn, and here’s why you should visit. This intro makes it sound like I’d never been to Shelter Island before but, in fact, I’ve popped over for dinner with family who live in nearby Sag Harbor. I loved the feeling I got when I first visited and always felt eager to return to the little island. This month, I finally had the chance to revisit when Edwin and I snuck up for two nights. I loved it so much so I’m excited to share a travel guide to Shelter Island with you today!

Here’s the gist, Shelter Island is tucked between the North and South Forks of Long Island—you can call it the Hamptons but it doesn’t have the flash of other Hamptons towns, which is exactly what makes it so special. It feels to me more similar to what Sag Harbor used to be. I knew I’d enjoy our stay but the truth is, I absolutely love, love, loved it. Shelter Island surprised me at every turn – here’s why you should visit… it has quiet beaches, tree-lined roads, and a slow pace that makes you feel like you’re in the exact right spot at the exact right moment. You will simply never want to leave. The highlight of our stay was The Pridwin Hotel, which manages to feel both nostalgic and completely fresh at the same time. It’s the kind of place that makes only two nights feel like a true escape. It’s a place we already know we’ll return to time and time again. It has that intangible “this must be the place” feeling that you can’t manufacture. It’s a holdover from another time (the hotel is just barely shy of her 100th birthday) so it just feels right.

A Travel Guide to Shelter Island

How to Get to Shelter Island

Depending on how you slice it, getting to Shelter Island can take not just planes, trains, and automobiles but also boats! In all seriousness, you’ll love this because it deters some people from finding their way to Shelter Island, making it all the more magical for the people who do visit. It feels like a world away yet reaching Shelter Island is much easier than you’d think. And getting there is part of the fun! Driving a car onto a ferry will literally knock the sock off my boys—they will think it’s so cool, the way only 3 and 4-year-olds can.

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A Room With A Table Chairs And A Painting On The Wall

Why The Pridwin Is the Only Place to Stay on Shelter Island

If Shelter Island has one must-stay spot, it’s The Pridwin Hotel. Originally built in 1927 and recently refreshed in the most beautiful + authentic way, it’s the definition of classic summer Americana. Think Adirondack chairs on the lawn, kids running between the woodsy tennis court and the water, couples sipping cocktails on the deck at sunset (aka us!) – it’s old-school charm with every modern comfort. The Pridwin is what really surprised us about the trip. I had no doubt that we’d enjoy our stay – it looked amazing on Instagram, after all – but I had no idea we’d flip for it the way we did. Edwin captured it perfectly; he equated it to a Northeast version of The Gasparilla Inn. It is so friendly and welcoming, beautifully appointed but in the most familiar and approachable way, it is upscale but laidback at the exact same time, it is brimming with character and rooted in history. It’s the good stuff. A travel guide to Shelter Island wouldn’t be complete without it.

We found The Pridwin to also be the type of place where you notice yourself chatting with the couple at the bar next to you or the family playing lawn games beside you at sunset. Conversations inevitably led to “where are you from?” to which we were always met with “Charleston, wow! How did you find this place?” I hate to even write this blog post because the hotel does, in many ways, feel like a hidden gem. I’m a person who has eyes on and I’m a bit of a magpie for hotels but everyone we met was from the Northeast and was surprised we knew to come. I had no idea it was, in the minds of some, under the radar because it has very much been on my radar since it’s full refresh but the cats out of the bag I’m afraid! It’s fantastic! Here’s what makes it so special:

Activities for everyone. Tennis, pickleball, boating, a spa, a pool, lawn games, mokes, bikes, kayaks, and a private beach mean you can be as active or as relaxed as you want.

We played pickleball, enjoyed the pool, took a moke into town, relaxed on the beach, jumped off the dock, and did an evening boat cruise (with rosé and a picnic basket full of lobster rolls and potato chips!), and played an an exhaustive amount of cards on the deck. We couldn’t have been happier! There’s also more than one golf course on the island for those that play.

Beautiful gathering spaces: From the expansive deck overlooking the water to cozy lounges filled with board games and vintage details, there’s a spot for every mood and everyone. There’s a game room for kids and adults alike (sounds corny, it’s not), a room called The Nook where they play classic movies at night (we watched Indiana Jones one night after dinner with personal popcorn bowls – it was too much fun!), and a gorgeous lawn polka dotted with corn hole, kids running around, and adults milling about, cocktails in hand, watching the sunset all while kids drop lines down below off the dock and boats come and go all evening long. I’m not exaggerating in the slightest, it is as magical as it sounds.

Food & drinks: The Terrace, the hotel’s restaurant, serves fresh, local dishes for breakfast, lunch, and dinner while two different bars give you options for a casual afternoon drink (the outdoor poolside bar) or a more lively evening cocktail (prettiest bar off the terrace!).

“ From the expansive deck overlooking the water to cozy lounges filled with board games and vintage details, there’s a spot for every mood and everyone.”

Perfect for couples and families alike: It’s just as easy to spend a romantic weekend here as it is to bring the kids. We talked to so many families who loved the cottages, scattered around the property, for traveling with their kids. If I had a dollar for every time we said, “we can’t wait to come back with the kids!” well, then I’d be able to pay for that trip in full already.

Sunsets like nowhere else. Watching the sun dip into the water from The Pridwin’s deck is reason enough to visit. It’s a nightly event that never gets old.

One night during sunset, I babbled on to Edwin about how I love the human experience and the human race because of sunsets. No one sunset is alike so there’s something innately human about stopping everything to watch a sunset. They never cease to bring a smile.

The seasons: It was absolutely perfect in the summer but I now keep saying to Edwin that we just have to experience it in the fall. Vibrant fall leaves set against the water, chefs kiss! From what we could see while we were there, it looks like the hotel does a lot of fun fall programming for guests too. Pumpkins, s’mores, sign me up (again, my kids would be in Heaven!). The Pridwin manages to capture that “summer camp for grown-ups” feeling while also being an incredible family destination. I have to admit, it’s rare to find a place that balances both so well. I’m always searching for such spots, but not always finding them!

Our Itinerary

Here’s a look at how we spent our days on Shelter Island:

DAY ONE

Arrive on the Island at lunchtime (we had an early flight), stop at Marie Eiffel Market for a delicious lunch on the waterfront deck (also a great spot to pick up some yummy provisions), window shop at a few shops right there by the restaurant, check-in at The Pridwin, walk around exploring the property, corn hole on the lawn, sunset cocktails on the deck with a side of gin rummy, a walk down the beach to dinner at Sunset Beach (The Pridwin and Sunset Beach are about a half mile from each other, which is so fun! I’d been to Sunset Beach before for dinner and it never disappoints because the ambiance is that good), walk back to The Pridwin (I wore a sweater – the dream!), homemade pie for dessert, watch Indiana Jones with popcorn in The Nook, bed!

DAY TWO

Morning reading in lounges on the deck followed by breakfast outside on the deck, pickleball, a little bit of work in the most beautiful common space room off of the terrace restaurant, a Moke to town to buy the kids shirts at Bliss, relaxed afternoon by the pool, running and jumping off the dock into the water, evening sunset boat ride around Shelter Island on Fred’s Folly, gin rummy and margaritas on the deck, dinner al fresco on the deck, homemade pie for dessert (I can’t pass up pie, it’s simply not in my constitution).

DAY THREE

Visit family in Sag Harbor. If we had one more day on Shelter Island, we would have taken bikes to see some of the neighborhoods we saw by boat the night before, made spa appointments, read more, walk/hiked Mashomack Preserve, and paddle boarded.

Jillian Attaway In A White Dress Holding A Glass Of Wine And A Person In A Black Dress

Travel Guide

More to Explore on Shelter Island

While The Pridwin could easily keep you entertained for an entire stay, Shelter Island itself has a lot to offer:

Crescent Beach, Menhaden Lane Beach, Shell beach, Wades Beach, and Kissing Rock for swimming and people-watching.
Mashomack Preserve for hiking + great views.
Local dining at Léon 1909 for French-Italian dishes, Vine Street Café for local quaint cottage-style delicious food, Marie Eiffel Market for delicious, casual waterfront lunch + provisions, Sunset Beach for a vibe-y beachside meal, and Tuck Shop for ice cream.
Haven House and Sylvester Manor for a little history of the island
Haven’s Farmers Market and Sylvester Manor Farm Stand for a taste of the island

I hope this post, A Travel Guide to Shelter Island, was helpful! We were so surprised by just how much we loved it and by how sensational the hotel was in every way. It made our stay. It gives off a familiar happiness you can’t quite put your finger on. Even if you’ve never been, it still feels familiar. The nostalgia the property is dripping in makes it feel effortless, beautiful, familiar, easy, and inspiring. The island is laid-back but full of beauty and nature, simple but never boring, and classic in a heritage Americana way. With The Pridwin as your home base, it’s the kind of place you’ll want to return to year after year. I have a very strong feeling we will! I know you’d love it just as much as we did!