I have fond childhood memories of sailing across the Long Island Sound from Connecticut and cruising into Shelter Island on a small boat to dock and dine. Almost 30 years later but the memories still strong, I returned to the island. This time I was reuniting with my friend Katy aboard the New London ferry as she wanted to introduce me to her childhood summer getaway once again and was eager to share how she was helping preserve and restore an arched white bridge from 1907 that managed to withstand the test of time.

The 27-square-mile island is literally sheltered (or sandwiched) between the north and south forks of Long Island – about two and a half hours (90 miles) east of New York City. Once the home of the Manhanset tribe of Indians, Shelter Island is now home to retirees and longtime locals and often caters to the uber-wealthy or those who have had family homes passed down for generations. It can only be reached by ferry from Greenport, N.Y. on the North Fork or North Haven, N.Y. on the South Fork.

Unlike other Hamptons stomping grounds, this haven has continued primarily as a peaceful escape, often one for those seeking a new post-pandemic existence or a break from chaotic city life. As we zipped onto the island in our Tesla off the second ferry from Greenport, it wasn’t long before we spotted groups of deer and wild turkeys with their babies. I admired wooden clapboard homes from the 1800s, something so foreign now after living in Los Angeles for 17 years. The island’s natural beauty and timeless character felt like being sent to summer camp.

Step back in time and get to know this sleepy isle.


Leon 1909
The buzzy new restaurant on the island – with a warm natural wood interior centered around a central wood-fired hearth and outdoor patio – serves uber-satisfying wood-fired dishes with Mediterranean flavors and an emphasis on seasonal and local ingredients. Share blistered veggies, whole roasted fish, or roasted clams with fennel sausage. The low-fired half chicken with herbed salsa verde is highly talked about for a reason. Leon’s house-made bread, chicken liver pate, and fresh tuna tartar are standouts and any happy communal affair should continue with Leon’s crisped Strozzapreti and Chimichurri hanger steak with summer squash. It was impossible not to ogle the hefty Leon burgers at the table next to us – topped with gruyere, caramelized onions, and sour pickles. Brunch is also available along with an extensive wine list and stellar cocktails; an Espresso Martini, Mezcal Al Fresco Bianco, and scotch lemon ginger Penicillina.


 The Pridwin
This timeless seaside resort hotel (est 1927) with cottages and restaurant perched above Crescent Beach is like stepping into a Wes Anderson film or the Dirty Dancing set location.

After a two-year renovation, old meshes with new – cozy fireplaces, classic sailboat art, and the same white exterior with hunter green window casements. Put on your polo shirt and find a spot on the wraparound terrace for stunning sunset cocktails.


Sylvestor Manor Educational Farm
Since 1652, Sylvestor Manor has been home to 11 generations of its original European settler family. Once a Native American hunting, fishing, and farming ground, the place has been transformed from a slaveholding provisioning plantation (for the Barbadian sugar trade), to an Enlightenment-era farm, to a pioneering food industrialist’s estate, and today as an educational farm. This nonprofit organization includes a historic plantation and Manor House, arts and education programs, an 1810 Dominy Windmill, and a seasonal Farm Stand with organic produce and meats.

Open to all from sunrise to sunset, walk the trails (dogs on leash permitted) through farm fields, wet and woodlands, formal gardens, grass lawns, and numerous barns and buildings or participate in one of their family or summer youth programs.


Perlman Music Program
Feel the beauty of the land and surrounding nature with a free “work in progress” concert from genius musicians ages 12-18 outdoors as young string instrument prodigies thrive here in the summer months thanks to The Perlman Music Program. Founded in 1994, musical training for young musicians is led by Itzhak Perlman and world-class faculty.


Shell Beach
Walk this narrow, secluded beach peninsula sandwiched between waterways and loaded with shells, like toenail shells and knobbled welk with their orange interiors. Calm oceans invite you to kayak or swim around the point.

Mashomack Preserve
Considered one of the richest habitats in the northeast, the preserve covers nearly 1/3 of the island and makes a wonderful place to hike with over 10 miles of trails, five well marked. Edged by 11 miles of coastline, The Nature Conservancy’s wildlife refuge offers 2,350 acres of interlacing tidal creeks, mature oak woodlands, beech forests, and marshes.


Seven on Shelter
Coming from Los Angeles, it seems impossible to imagine a place that allows self-check-in with your key waiting for you in the door – a place so safe that locking your room appears to be optional and feels downright comical or inspiring in 2023. Welcome to Seven on Shelter, created with love from a former art gallerist and curator who moved to the island for more wall space to accommodate her growing collection. While it may feel like staying at your friend’s east coast home, this newly restored 1902 farmhouse turned boutique bed and breakfast hotel comes with a grand heated pool hugged by red umbrellas and comfy chaise loungers, with various whimsical art-filled seating areas to socialize or find a book to remind you that you stumbled into the good life.

Guests can also expect brand new bathing facilities in the stylish rooms and the promise that you’ll get to know your interesting neighbors if you stay long enough. Each morning, arise to a complimentary French-inspired breakfast prepared for guests in the kitchen, including fresh coffee, croissants with jams, cheeses, hard-boiled eggs, yogurt, and berries. For those who don’t want to miss a workout while traveling, a poolside fitness room includes rowers, yoga gear, and a spin bike. Just a few minutes walk down the road, spend a day swimming at Sunset Beach or watching the famous west-facing sunset from the summer’s yacht-filled oasis, the seasonal Sunset Beach Hotel.

Shelter Island truly feels like a place where time stands still.

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