At the fishtails that are the eastern end of Long Island, N.Y., visitors enter a magically bucolic world, where the setting is simple and relaxed even at the peak of tourist season. How could it not be? Separated from the hustle and bustle of Greenport on the North Fork and the Hamptons to the south, “The Rock,” offers a wonderfully convenient place to get away from it all just a 15-minute boat ride from more chaos if you need it.
Enjoying down time is exactly what most visitors to Shelter Island plan to do. Dering Harbor is the most popular place to tie up, as it anchors the island’s small shopping district affording easy access to provisions, fine dining, a liquor store and a pharmacy. The setting may seem modest as you step ashore but that doesn’t mean you’ll go without, as there are two marinas residing side-by-side here. For some don’t-miss shopping, stop in Marie Eiffel, a fashion boutique, or rent some bikes at Piccozzi’s Garage & Bike Shop and venture to Shell Beach — a secluded stretch that juts out into Shelter Island Sound.
If you would rather just get away from it all, stay overnight in beautiful Coecles Harbor on the Northeast side of the island and catch a magnificent sunrise. For a short cruise inland and a peek at waterfront homes, pull into West Neck Harbor on the island’s southwest corner. This tight but navigable passage also affords dockside access to SALT Waterfront Bar & Grill, one of the island’s premiere dining experiences. Dress casual and be sure to visit the onsite Shipwreck Bar — it’s actually the hull of a ship.
Shelter Island may be small at only 8,000 acres, but there is always something going on here. The winding roads are perfect for biking or jogging if you don’t mind some hills. Those who like to wet a line will find that fluke, porgy and blue fish rule the summer and stripers patrol the rocky shoreline come fall. More passive nature lovers can head over to expansive Mashomack Nature Preserve to hike. Be on the lookout for osprey and their nests. Finally, a perfect place to unwind is Sunset Beach Restaurant, sipping on a cocktail while watching the day come to an end — with a spectacular sunset.
Where to Eat
- The Pridwin (81 Shore Rd., 631-749-0476) is known for its famous tuna burger and tuna steaks caught fresh in the waters around Shelter Island.
- SALT Waterfront Bar & Grill (63 S. Menantic Rd., 631-749-5535) offers an assortment of contemporary American food including Shelter Island clam chowder and Korean BBQ. Salt also has a great Tiki bar.
Where to Dock
- Coecles Harbor Marina & Boatyard includes a swimming pool, free WiFi, diesel fuel and pumpout.
- Piccozzi’s Dering Harbor Marina is a full-service facility with fuel, laundry and showers and accommodates vessels up to 160 feet.
Getting There by Boat
Approaching Dering Harbor from the east, stay south and west of Long Beach Point to avoid shoaling. If coming from the mainland, figure Dering Harbor to be roughly 20 nautical miles from Old Saybrook, Conn., 37 nm from Bradford, Conn., and 27 miles from Stonington, R.I.