Visit the Hamptons and Shelter Island
Visit The Hamptons and Shelter Island
When you visit the South Fork of Long Island, you step into a world of luxury. Feel like a celebrity while walking down the streets of the Hamptons, or enjoy a coastal getaway unlike any other on Shelter Island. Enjoy three days of coastal elegance and island charm by setting off on this itinerary made just for you.
Day 1
Start your Hamptons visit with a trip to Downtown Sag Harbor. This historic whaling village is now home to several boutique shops, waterfront views, and cafes full of life that stand out against the rest of the Hamptons. Take a stroll down Main Street and see what’s waiting for you.
As sunset falls over the horizon, you’ll want to head to Cupsogue Beach to see it. Westhampton’s miles of soft sand and Atlantic Ocean make this the ideal sunset spot of the Hamptons. When night comes, check into Barons Cove, an upscale waterfront retreat with cozy-chic rooms that are just steps away from Main Street.
Cupsogue Beach County Park
Day 2
Enjoy a day of art and wine along the South Fork! Immerse yourself in the local art scene when you visit Guild Hall of East Hampton. Inside, you’ll find visual art exhibits, theater. live performances, and more.
Head to Sagaponack next to have a taste of the Long Island wine scene. Wolffer Estate Vineyard, one of the few vineyards in the Hamptons, offers world-renowned rose and artisanal bites along the vines.
Day 3
With your Hamptons checklist complete, take the ferry out of Sag Harbor to Shelter Island where you’ll enjoy scenic views of Peconic Bay along the way. Looking for a quiet spot to unwind when you arrive? Head to the secluded Shell Beach. This calm stretch of sand is the perfect place to go kayaking, find some shells to take as a souvenir, or just unplug.
Check into the Ram’s Head Inn for the night, a beautifully restored inn now included with modern amenities. You’ll find rooms with wraparound porches and even onsite dining to top off your relaxed Shelter Island visit.
