Our Endless Summer Guide to Shelter Island

That's the spirit behind our Endless Summer campaign with The Pridwin on Shelter Island, a historic waterfront retreat that inspired a season of optimism, color, and effortless style. With colorful interiors, timeless coastal charm, and days filled with tennis matches, boat rides, and sunset cocktails overlooking Peconic Bay, it was the perfect backdrop for a collection of vibrant new hues, versatile dresses, elevated separates, and easy layers.

Designed for every moment between now and Labor Day—and every adventure that comes after—our Endless Summer collection feels right at home on Shelter Island.

Here's our guide to experiencing it for yourself.

Stay at The Pridwin & Why We Love It

A beautifully restored waterfront retreat set on ten acres overlooking Peconic Bay, The Pridwin is everything we love about an East Coast summer.

Here, everything you need is right outside your room: tennis matches by the water, boat rides around the bay, lawn games, beach days, sunset cocktails, and the kind of nostalgic moments that make you want to return year after year.

Celebrating its 100th birthday in 2027, The Pridwin has welcomed generations of families to Shelter Island for nearly a century.

Following a thoughtful restoration by owner and designer Colleen Bashaw, every space is layered with cheerful color, playful patterns, collected antiques, and timeless coastal charm.

Equal parts nostalgic and fresh, it's a place that invites you to slow down, savor the season, and enjoy every colorful moment.

P.S. We have an exclusive booking code for you! https://www.caperesorts.com/pridwin/packages/lilly-pulitzer-exclusive-offer 

Where to Eat

The Terrace at The Pridwin

(our first reservation)

Order the Linguine with Clams—it's a signature for a reason. Don't skip cocktails featuring The Pridwin's collaboration with NYC's iconic Dante.

Léon 1909

A beautiful dinner destination serving a wood-fired menu with European influence.

Stars Café

The local breakfast spot for coffee, pastries, and people watching.

Marie Eiffel Market

Pick up French pastries, sandwiches, and provisions before heading out for the day. Enjoy breakfast or lunch on the back porch overlooking the harbor.

Tammy Fender at The Spa at The Pridwin

Palm Beach has arrived on Shelter Island. Book the signature holistic facial from legendary skincare pioneer Tammy Fender. Equal parts treatment and ritual, it's the kind of restorative experience that leaves you glowing long after you've returned home.

Finley's Fiction

First, pick out your summer read. Then, hop in a Pridwin Moke and take the scenic route back to the hotel to spend the afternoon poolside, book in hand, with nowhere else to be.

The Sunset Plan

Fred's Folly: Reserve the sunset cruise aboard The Pridwin's classic boat. It's the kind of late-summer moment you'll remember long after you've returned home.

Our order:

• A lobster roll picnic
• A chilled bottle of Château Minuty Rosé
• Golden hour on Peconic Bay

Explore Shelter Island

Mashomack Preserve: Hike miles of peaceful woodland and coastal trails through one of New York's most beautiful nature preserves.

Sylvester Manor: Wander the historic grounds, stop by the Farmstand for seasonal flowers and just-picked produce, and explore one of Shelter Island's most treasured landmarks.

Sweet Treat: You simply have to order The Pridwin's house-made Ice Cream Cookie Sandwich. Best enjoyed poolside.

In the evening, gather around the fire for homemade marshmallows and s'mores—one of The Pridwin's sweetest traditions.

If It Rains

The Pridwin was made for cozy afternoons: 

• Ping pong in the Game Room
• Jenga in The Nook
• Backgammon in the Living Room
• A good book and one more cocktail before dinner

Sometimes a rainy afternoon is part of the charm.

Entertainment

Every Tuesday evening, head to The Grove, The Pridwin's intimate outdoor amphitheater, for live music beneath the trees where an outdoor bar and fireside s'mores await. It's one of our favorite summer traditions! 

Explore Beyond the Island

One of our favorite things about a stay at The Pridwin is how easy it is to turn a weekend getaway into an even bigger adventure. When you're ready to explore beyond Shelter Island, both the North and South Fork are just a short ferry ride away.

North Fork: Spend an afternoon vineyard hopping, browsing farm stands, and exploring charming waterfront towns at a slower pace.

South Fork: Looking for a change of scenery? Hop the ferry to Sag Harbor for shopping, galleries, and a leisurely stroll through one of the Hamptons' most picturesque villages.

See you on Shelter Island! xx Lilly