This 8,000-acre coastal getaway bypasses the Long Island Expressway headache for calm waters and a historic 1650s estate

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Natalia Alvarez

 ·  May 30, 2026

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This 94-Mile Coastal Route Might Be One Of New York’s Most Scenic Summer Drives—Connecting Breezy Beach Towns & The State’s Oldest Lighthouse

New York’s Best-Kept Secret For A Summer Drive: This Idyllic Waterfront Route Is Home To 60+ Vineyards And One Of NY’s Most Iconic Lighthouses

Looking for the ultimate summer escape without the bumper-to-bumper Long Island Expressway headache?

Tucked quietly between the North and South Forks, Shelter Island is a serene, ferry-access-only retreat that completely bypasses the typical Hamptons crowds.

With its Mediterranean-style beach clubs, calm waters, and secluded coves, it offers New Yorkers a cinematic, European-style summer getaway right in their backyard.

It has the exclusive, sun-drenched feel of the French Riviera, but you can reach it in just a couple of hours.

A slice of preserved history

The island has deep roots, originally inhabited by the Manhanset tribe who called it Manhansack-aha-quash-awamock, which beautifully translates to “Island sheltered by islands.”

From its early days as a 17th-century provisioning plantation to its late 19th-century boom as a summer resort, the area is packed with fascinating heritage.

You can visit Sylvester Manor, a historic estate dating back to the 1650s, or wander through the Heights to admire the perfectly preserved Victorian-era summer cottages.

Pristine nature and beaches

Spanning around 8,000 acres, nearly one-third of the island is protected by The Nature Conservancy. The Mashomack Preserve is an absolute dream for nature lovers, offering incredible bird-watching and hiking trails that range from quick 1.5-mile walks to immersive 11-mile treks.

Of course, a Shelter Island beach getaway isn’t complete without hitting the sand. The island is surrounded by the gentle waters of Shelter Island Sound and Gardiners Bay. Grab your sunscreen and head to:

• Crescent Beach: Famous for its stunning sunset views and lively shoreline atmosphere.
• Wades Beach: A spacious, family-friendly spot with incredibly gentle waves.
• Shell Beach: A secluded, narrow strip perfect for peaceful, quiet strolls.

🚢How to get there

You can’t drive directly onto the island, which is exactly how it keeps its peaceful charm. It is only accessible by a short ferry ride.

You can hop on the North Ferry from Greenport (about an 8-minute trip) or take the South Ferry from North Haven (a quick 5-minute crossing).

Once you arrive, you’ll find a tight-knit year-round community of about 3,200 residents, though the population safely swells to over 20,000 during the peak summer months.

Plan your escape

📍 Shelter Island, NY (Suffolk County)

🚢~2.5 hours from NYC

📅 May through September (Peak season)