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Michelle Smith’s Guide to Shelter Island

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She’s back! Milly’s Michelle Smith gives her tips for summering on Shelter Island just in time for the last long weekend of summer. Kick back and listen up!

To Shelter Island! My kiddos are always game for a field trip, and Shelter Island has been our go-to for years.

Getting there: The Shelter Island ferry is always an option, but I prefer to arrive in style! Round up the squad—and a friend with a really nice boat—and enjoy a speedy ride over. Dock up at one of The Island Boatyard’s day slips, where you can catch some live music and a cocktail later in the day!

What to do: My first stop is Piccozzi’s Bike Shop, where we rent bikes and explore one of the many scenic bike routes. From there, it’s kayaking, exploring the Mashomack Nature Preserve, sailing lessons at the Shelter Island Yacht Club, or heading to the beach.

Where to dine: Sunset Beach Restaurant Café & Bar, for a little taste of the French Riviera and coastal Italy.

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