10 a.m.: Hop on the Ferry
Start your day by taking in the stunning views on the ferry ride to Shelter Island. The South Ferry shuttles visitors from North Haven to the island every 10 to 15 minutes from 5:45 a.m. to 1:45 a.m. Pro tip: If you’re not bringing your car or a bike across, take the North Ferry out of Greenport, as there’s a bike rental on that side of the island.
10:30 a.m.: Enjoy Baked Goods
After the 10-minute ferry ride, head to the north side of the island for breakfast at Marie Eiffel Market, an adorable patisserie that feels like it was transported from a side street in Paris (maybe because it’s run by a French expat). A croque madame and an almond-pear tart should be plenty of fuel to get you through the morning.
11:30 a.m.: Kayak the Harbor
Time to explore: Rent a kayak or take a guided tour with Shelter Island Kayak for a serene, up-close look at some of the island’s waterways. The calm harbor is ideal for kayakers of any skill level (including kids), and you’re likely to spot turtles, fiddler crabs and other critters.
1 p.m.: Eat Amazing Seafood
After working up an appetite with all that paddling (hey, triceps), it’s time for lunch. Local favorite Salt offers a daily raw bar, lots of large plates of locally caught seafood—ideal for sharing—and summery, easy-drinking cocktails (like the watermelon-basil One in a Melon).
2:30 p.m.: Hunt for Treasures
Post-lunch, window-shop the island’s collection of charming shops. Book lovers should stop into Black Cat used bookstore and hunt for first editions of their favorites.
4 p.m.: Take a Walk with a View
Head back toward the south part of the island for a hike in the Mashomack Preserve, which covers 2,039 acres (a full one-third of the island). The mix of freshwater marshes, tidal creeks and oak woodlands make for a great place to spot ospreys and other wildlife.
7 p.m.: Finish the Day with Pasta and Live Music
Before hopping on the ferry back to the South Fork, stop at casual Vine Street Café for linguine and shellfish fra diavolo and a superb wine list. Afterward, swing by The Ram's Head Inn for cocktails (and, if it happens to be Sunday, live jazz).
9 p.m.: Head Back…or Don’t
Not ready to say goodbye to the peaceful surroundings? Grab a room at The Chequit, a charming seaside inn that ticks every box on our lodging wish list: bright, luxurious quarters, breezy porch for lounging and complimentary breakfast.