Curator’s statement
Shelter Island, a hidden gem nestled between the North and South Forks of Long Island, New York is a popular weekend getaway from New York City. It’s a nature lover's paradise with its pristine beaches, lush landscapes and charming local shops. This quaint island offers a tranquil retreat, perfect for a weekend getaway.
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Day 1: Arrive at Shelter Island
From Manhattan on a good day, the drive is about 3-½ hours. An east-end trip wouldn’t be complete without stopping at the lavender fields. Here you can stroll through the fields and enjoy the calming ambiance as a prelude to your weekend Lavender by the Bay.
Once on the island, stop at the Pridwin Hotel for lunch on the Terrace with a view overlooking Crescent Beach.
Check into your hotel. Once checked in, grab a bike. Most hotels offer free bikes to tour the island. If biking isn’t your idea of relaxation, go for a leisurely walk, taking in the natural beauty and serenity of this island getaway.
For drinks and dinner, head to the Rams Head Inn Grab a cocktail and stroll through the beautifully landscaped grounds. Say hello to the adorable sheep and check out the organic gardens and beehives.
Dinner is served on the veranda with stunning sunset views of the water through the trees. Make sure to order the honey buns, deliciously homemade with their signature Rams Head Inn honey butter.
End your evening at the Sunset Beach Bar or if you are looking for a more relaxed evening, grab a book and cozy up in your room.
Day 2: Kayak and drive to the Mashomack Preserve
Start your day with breakfast at your hotel. Then head out onto the water to kayak or SUP.
After checking out, drive to the Mashomack Preserve to walk the sprawling nature reserve. The preserve has a boardwalk and trail system with distances from a quarter-mile to just over three miles. Here you might spot deer, ospreys and other wildlife while enjoying the views and woodlands.
Before you get on the ferry for your drive back, stop at Stars Cafe for a quick bite or take-to-go for the journey home.
Need to know
Getting to Shelter Island: The Island is accessible only by Ferry Service from the North Fork of Long Island in Greenport and the South Fork in Sag Harbor. The ferries on either side are frequent, so you don’t need a reservation. Just hop in a line that reads “Ferry Lane” upon arrival and drive onto the ferry for the 10’ ride to the island. Traffic is boarded on a first-come, first-served basis. There are a few differences in pricing/duration depending on which one you choose. Please consult with the Ferry Companies for schedules and fares:
North Ferry Information: www.northferry.com | You can only purchase your tickets on the ferry with cash or check. North Ferry Tickets– Greenport ($15 one way, $24 round trip).
South Ferry Information: www.southferry.com | The South Ferry allows you to pay with cash, credit card or online. South Ferry Tickets – Sag Harbor ($15 one way, $20 round trip) +$2 per person, $3 R/T.
Travel Advisor
Jill Bauman
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This itinerary is part of our ongoing series on travel to New York.