Guide to Shelter Island: Things to do, lodging and more 

Shelter Island, located between the frenzied Hamptons and increasingly buzzy Greenport, has no movie theater, nightclub or shopping center to draw traffic or crowds. Instead, miniature golf, sailboat races and beach barbecues serve as entertainment in this tranquil paradise. Here are some tips for experiencing this quiet eye in the center of the Twin Forks’ storm.

HOW TO GET THERE

Unless you have your own boat, you’ll have to take a ferry from either Greenport or North Haven. Both the North and South Ferries are cash only, no reservations, and leave every 10 to 20 minutes. Both ferries accept walk-on passengers for $2, and bicyclists for $4 (North Ferry) and $6 (South Ferry). 

The North Ferry (northferry.com), which runs from Greenport to Shelter Island, operates from 5 a.m. to 11:45 p.m. (and until 12:45 a.m. on Friday and Saturday from Memorial Day through Labor Day). Cost is $14 per vehicle, $22 same-day round trip.

The South Ferry (southferry.com), which runs from North Haven to Shelter Island, begins service at 5:40 a.m. The last ferry leaves Shelter Island at 11:45 p.m. Sunday through Thursday, 1:45 a.m. on Fridays and Saturdays (from late June through Labor Day, the daily hours are 5:40 a.m. to 1:45 p.m.). Cost is $15 per vehicle, $20 same-day round trip. 

THINGS TO DO 

With 20 miles of coastline, it’s not surprising that beachgoing is the most popular summer activity here. On the south side of the island and fronting Shelter Island Sound, Wades Beach is popular with families for its wide stretch of sand, shallow swimming area, lifeguards and restrooms. For people-watching, Sunset Beach, also known as Crescent Beach, is the place; across from Sunset Beach Hotel, it is the island’s most popular spot, filled with designer-clad bathers. Less accessible, and thus quieter, is Shell Beach, a narrow spit of sandy beach extending into the water with West Neck Harbor on one side and Noyack Bay on the other. Beach parking is only by permit between mid-May and mid-September; daily permits available online (shelterislandchamber.org) for $25 and are sometimes offered gratis by hotels.

End your day at the beach with a round of mini golf and some ice cream at the Whale’s Tale (shelterislandwhalestale.com). Another spot to explore is Mashomack Preserve (nature.org), which has 11 miles of coastline, trails and an abundance of birds to observe. For some water-focused fun, the Menantic Yacht Club, which is celebrating 90 years of racing, holds sunfish races every Sunday at 2 p.m. from the end of June through Labor Day in West Neck Harbor.

For shoppers, Shelter Island has a few standout retail spots. Black Cat Books (blackcatbooks.com) is a must-stop for rare- and used-book lovers. Marika’s Eclectic Boutique (marikasshelterisland.com) is a treasure trove of vintage furniture and home accessories, unmissable because of the large collection of colorful patio sets on the lawn in front of the shop. 

There’s plenty of culture here, too. Learn about the island’s history while exploring the grounds of Sylvester Manor (sylvestormanor.org), a historic plantation built in 1650 that now exists as a nonprofit organization and has trails that are open daily from dawn to dusk. A downloadable walking-tour app of the grounds will take you past the manor house, an Afro-Indigenous burial ground and more. The Perlman Music Program (perlmanmusicprogram.org) is an idyllic summer retreat for gifted young musicians. You can hear them play at the program’s annual summer gala on July 28 and at other events throughout the summer.

GRAB A BITE

Even the fine-dining establishments have a low-key vacation vibe. Léon 1909 (leon1909.com) serves Provençal-style cuisine and a selection of complicated cocktails. Vine Street Café (vinestreetcafe.com), which serves elevated comfort food like duck confit and lobster pot pie, has an expansive outdoor garden where diners can kick back and relax. 

If you want a waterside table, stop in at SALT (saltshelterisland.com) for sushi, seafood and fresh local salads. It features an outdoor repurposed sailing ship (known as the “Shipwreck Bar”) where barefoot patrons belly up for tropical drinks and then settle in to listen to live music daily (Memorial Day weekend through August). SALT also is adding Family Fun Day (June 27 through Labor Day) starring the “Goat on a Boat” puppet show truck. Shelter Island Craft Brewery (shelterislandcraftbrewery.com) offers hyperlocal brews on tap in its small tasting room and at outdoor tables. 

A best bet for breakfast includes the artisan bagelry Eccentric Bagel (eccentricbagel.com), which sometimes features off-menu specialty bagels. Shelter Island Slice (shelterislandslice.com) is a good option for pizza, pasta and sandwiches. 

OVERNIGHT STAY

Shelter Island boasts two classic hotels. The Pridwin Hotel and Cottages (caperesorts.com) is a resort property geared toward families with a private beach, pool, tennis, croquet and scheduled kids’ activities, plus a full-service restaurant and spa for mom and dad. Starting rate for an overnight stay is $594. The Chequit (thechequithotel.com), located within walking distance of the North Ferry, features a restaurant helmed by well-known local chef Noah Schwartz. The iconic porch and patio features several fire pits, and its pub has a pool table and flat screens where both guests and non-guests can stop by for a drink or catch sporting events on the tube. Starting rate for an overnight stay is $375.

KNOW BEFORE YOU GO 

• To avoid the $25 parking permit fee, walk or bike to the beach. Bikes can be rented at Piccozzi’s Bike Shop (jwpiccozzi.com). 
• No dogs are allowed on beaches from Memorial Day through Labor Day, so make sure you can leave Fido at your lodgings while you take in the sun. 
• In contrast, no permits are required for barbecuing on Shelter Island beaches. So bring your grill along with towels and sunscreen if you’d like.