Postcard from Shelter Island

Buggy and friends recently took a long weekend in Shelter Island, trading the city’s hum for ocean breezes and coastal charm. Between a leisurely dinner with friends and a sunlit boat ride filled with laughter and rosé, the days unfolded with an easy rhythm. 

Just a few minutes by ferry from the Hamptons, Shelter Island captures a nostalgic, frozen-in-time charm while still feeling fresh. Here’s how to spend the perfect long weekend. 

SHELTER ISLAND TRAVEL GUIDE

Stay

• The Pridwin Hotel & Cottages
  Recently renovated, The Pridwin feels like an elevated adult summer camp. Its airy, light-filled rooms bring a modern polish while still nodding to the timeless Americana.

 

Stephanie in the Coral Halter

Lunch

• Marie Eiffel Market
  A local favorite that’s part café, part market. Order fresh sandwiches or salads and eat out on the waterfront deck. Afterward, browse the shops in the village—it’s a perfect midday outing.

Drinks & Dinner

• Vine Street Café – The island’s go-to dinner spot, where the food is consistently good and the Machete cocktail is practically famous.
• Sunset Beach – Just minutes from The Pridwin, vibe-y beachside spot with euro, lively energy. 
• The Pridwin – Stay in for dinner at the hotel, or grab drinks at the bar.  This fall they’re partnering with NYC’s Grand Banks for a culinary collab. 

Sweet Treat

• Tuck Shop Ice Cream ParlorThis beloved, old-fashioned ice cream shop is pure nostalgia. Order a cone and take a sunset stroll—you’ll feel like you’ve stepped back into a classic summer vacation.

Stephanie in the Fête Dress

Buggy in the Fête Dress

 

Things To Do

• Mashomack Preserve – Walk Mashomack Preserve, more than 2,000 acres of tidal creeks, oak woodlands, freshwater marshes, and fields
• Beach Time – swim or lounge at The Pridwin’s beach, or soak in the more social scene at Sunset Beach.

Buggy in the Starfish Halter