Island. The very word conjures a place apart from the rest of the world. Bermuda, or perhaps the Caribbean; boats and sunshine and the sound of the ocean; lemonade on shady porches. Islands are usually so lovely, in part, because they so hard to reach.
There is one island, though, that is only two hours away by two pleasant ferry rides from Connecticut: Shelter Island.
Shelter Island is an 8,000-acre jewel nestled between North Fork and South Fork of Long Island, surrounded by azure Gardiners Bay, Shelter Island Sound and Peconic Bays. This island has been a seasonal retreat for generations of families. I had the good fortune to grow up summering on this island, and I still return to my family's house there every year.
The people who have made this island home have stamped their history into its architecture and culture for hundreds of years. These days, you can find old-fashioned gingerbread cottages next to chic restaurants and come-as-you-are bait-and-tackle joints.
Although there's been some noticeable "Hamptonization," the island retains a unique vibe. The beaches are never very crowded, the service in stores and restaurants is friendly, the water amazing for sailing and swimming, and the country roads scenic and uncrowded for bicycling. Hawk-like ospreys, miles of pristine beaches, salt marshes, three marinas, three deep-water harbors and an old-school yacht club lure visitors from throughout the world to this tiny island.
A particularly good way to enjoy Shelter Island is by bicycle. One caveat, though: If you haven't biked in a while, perhaps this isn't the best place to start. Not because the roads are busy—some days, the only traffic consists of deer and joggers—but because there are some fierce hills. Bikes are available for rental at Piccozzi's Bike shop in the Heights.
One of many special things about Shelter Island is that it's reachable only by ferry. Two companies serve the island, one from the North Fork, the other from the South Fork and the Hamptons. Most Connecticut visitors will come from the north, which is the prettier way to steam into town.
Right as you get off the ferry, you'll enter the remarkably picturesque Heights. Here, you'll find a collection of Victorian-era cottages—gingerbread, porches and wicker furniture included. The area feels like a step back in time. Indeed, the Heights was developed as a Methodist retreat in the 19th century. The 1873 Union Chapel in the Grove, a nondenominational chapel, is the centerpiece of the neighborhood. This Carpenter Gothic-style chapel has exquisite windows created by Shelter Island artist Walter Cole Brigham using local iridescent glass, polished pebbles and seashells. These Tiffany-like windows alone are enough to inspire devotion.
If your needs are on a more earthly plane, another former Methodist monument, the Chequit Inn, is happy to oblige. Built in 1872 as the dining hall and gathering venue for hungry parishioners, the inn now serves as a restaurant and hotel. The capacious porch is a particularly good place to people-watch, and the weary traveler can find sustenance here. Taking in the view of Dering Harbor, we've dined on calamari, fresh mussels steamed in white wine and garlic, Caesar salad, grilled chicken salad, iced tea, wine and beer. The lunch entrees range from $5.50 to $16.50, all worth the price. After all, what says summer more than a leisurely meal outdoors?
Beaches Aren't Crowded
Next up, the beach. If you feasted as we did, you'll probably be riding a little bit slower at this point, but no matter; you're on island time now. Hay Beach (or Menhaden Lane Beach) is a beautiful public beach about 2 miles from the Heights. Here, the biggest crowd is usually a flock of seagulls. If you pull up a beach towel, you'll be rewarded with a dreamy view across Gardiner's Bay. Instead of people-watching, you can boat-watch: There is a lot of incoming and outgoing traffic toward Greenport, so there are plenty of beautiful sailboats.
If you're after a trendier scene, try Crescent Beach (Louis' Beach, to the locals), the place to see and be seen. Here you'll find a swath of smooth sand and the Sunset Beach hotel. This 20-room hotel was built in the '60s, but André Balazas, a famous New York hotelier, has updated it in a millennial style. Here, the sunglasses are large, the bikinis tiny and the drinks potent and pricey. If you want to feel like you're at St. Tropez-on-the-Bay, here's your spot. The hotel's outdoor restaurant offers on its luncheon menu Salad Niçoise for $19 or a Sunset Beach Gruyère Burger for $17. On weekdays, you can park your car here free for the day, but on weekends, the charge for all-day parking is $15. All the Shelter Island town beaches require a $35 nonresident parking permit, so parking at the hotel is a good option for access to a swim and beach lounging.
All chic New Yorkers, though, need some fiercely stylish and incredibly delicious pick-me-ups once in a while, and for this sort of fix, there's only one place on the island: Mark it With a G, a handkerchief-sized bakery behind a real estate office on Grand Avenue in the Heights.
Variety Of Food
Life on the Island revolves around sailing, going to the beach, swimming, fishing, boating, bicycling, walking, tennis and golf—there are two golf courses, one public, one private. Did I mention eating?
On Shelter Island, a good take-out sandwich or panini can be had just down the street from the Chequit Inn at the Sunflower Market Place. Or try Redding's Gourmet Market in the Heights across from Piccozzi's Marina and Gas Station for an upscale selection of take-out sandwiches, cheeses and groceries. Redding's has tables out front, and there's a nice view from Piccozzi's dock of the Shelter Island Yacht Club. Another choice is the bar and restaurant called the Dory—there's a red dinghy parked on the roof. The Dory offers a lovely view from the outdoor patio of scenic Gardiner's Creek. The fare is straightforward, good for families with children.
To experience a bit of Shelter Island's stunning natural beauty, the Island offers one of the largest undeveloped nature preserves on the East coast, covering nearly one third of the island. Off Route 114, the 2,039-acre Mashomack Preserve is owned and maintained by the Nature Conservancy. Miles of walking trails through hardwood forests, meadows and salt marches make this a nature lover's paradise.
Getting There And Back
Because it takes two ferries to get there, you'll need to start early to have a full day at Shelter Island. The Cross Sound Ferry leaves New London hourly starting at 7 a.m. The trip to Orient Point, N.Y., takes about 80 minutes. From there it's a 15-minute drive to the North Ferry terminal in Greenport, N.Y., for the 15-minute trip to Shelter Island. That's nearly 2 hours each way.
It's not cheap, either. The round trip will cost a family of three more than $175. The Cross Sound Ferry fare is $102.40 for the car and driver, plus $26.71 per passenger. The North Ferry fare is $13 plus $4 per passenger.
For a complete guide to past "daycations" around the region, visit www.courant.com/daycation.
