As we took the ferry across the bay and docked on Shelter Island we felt the tension melt off our shoulders. My husband and I have been taking trips to the forks for decades since his family is from Long Island, but we had never ventured to the tiny island tucked between the North and South forks. The gorgeous weather we were having was a good start to a few days away kid free before the school year kicked off. You can access the island only by ferry, a roughly 15 minute ride from either Sag Harbor via the South Ferry or Greenport, via the North Ferry. The island is mostly residential with little public beaches tucked away down side streets throughout the island, and a small hub of restaurants and shops not far from where the ferry drops you off on the north end of the island. But you can find a handful of hotels sprinkled throughout the island and many of them have been renovated since the pandemic. If you have grown tired of the hustle of the Hamptons or even the activity of downtown Greenport, Shelter Island provides the right level of respite, with plenty to keep you just the right amount of busy—or still. My husband and I had a lovely couple days away without the kids, but a family getaway there works, too. Here are a few must-see locations to put on your schedule.
Where to Stay
On the northeast corner of the island stretches Ram Island, a peninsula that was, at one time, an island of its own. When Joan Covey built Rams Head Inn in 1927, the island was accessible by car only at certain times of the month when the tide was low. For decades now, a road built on the narrow sandbar connects Ram Island to the main island year round, and as you drive across, the salt air, 360-degree water views and ospreys in flight recharge you like a deep breath. Current owner Aandrea Carter, who has a house in Sag Harbor, bought Rams Head Inn during the pandemic and renovated it for the modern traveler, but has kept much of the character and charm of the century-old inn intact. She fell in love with the property when she caught sight of it while boating with friends, and, as luck would have it, the former owners were ready to sell. She takes her role as custodian of the property’s history and natural beauty seriously. “Rams Head Inn is quiet and unpretentious luxury with a chic residential feel set in a beautiful campus of gardens with views of the waterfront,” says Carter. “A stay is much like visiting an elegant country home. It’s quite magical.”
Among all the hotels we visited during our stay, the Rams Head Inn had the most peaceful setting, with sweeping lawns dotted with Adirondack chairs overlooking the waterfront. The inn has a private beach with access to complimentary paddleboards and kayaks, and my husband and I took advantage of the opportunity for a peaceful morning kayaking around the bay. Pickleball and lawn games are at your disposal at all times. Rooms are simple with four-poster beds, frette linens, wood floors and no TVs. Bathrooms, which have been redone, are all in white with pedestal sinks and rain-head showers. “Every room is unique,” says Carter. “Many of our guests like to come multiple times to enjoy different experiences.”
“We want people to feel at home in peaceful surroundings,” says Carter, who raises babydoll sheep on the grounds. You can pick up some feed at the front desk if you want to give them a snack. “We want our inn to be a kind of salon where people gravitate to find interesting experiences such as book readings, jazz programs, friendly gatherings and wonderful meals. The inn has a history of attracting interesting people. A notable historical fact is [the first Shelter Island Conference on the Foundations of Quantum Mechanics], a gathering of nuclear physicists including Robert Oppenheimer, took place at Ram’s Head Inn in 1947, so intellectual curiosity is in our DNA.” Events are held weekly and year-round, adds Carter. Many of her repeat guests like visiting in the shoulder season, or in winter, for book readings, cozy fireside chats and live music.
Where to Eat
Whether you stay at Rams Head Inn or not, be sure to have a meal there. They serve lunch and dinner all week, as well as Saturday and Sunday brunch. Executive chef Adam West, a CIA graduate, puts the focus on sustainability and locally sourced ingredients. In fact, the inn has its own vegetable garden and apiary, and their homemade honey is sold on the premises. You’d be remiss not to order the sweet and salty melt-in-your-mouth honey buns as an appetizer. The crab bucatini is a local favorite but our green curry halibut, which was the special, served with crispy potatoes and spinach, was equally delicious. After dinner, you can have a glass of wine on the lawn, the patio or at the bar inside, which has a distinctive 1920s-meets-2020s vibe. In the summer, the restaurant and bar are kept open-air to let the sea breezes flow in.
If you are looking for a little more action, head over to SALT, where the boat and people watching is a lot of fun. Proprietors Keith and Ali Bavaro set it up in the Island Boatyard and Marina on South Menantic Road, and guests have the ability to dock for dinner. The eclectic menu has lots to choose from; don’t miss the local oysters and clams from the raw bar. Whether you arrive by land or sea, visit the Shipwreck Bar before or after dinner. It’s the restaurant’s outdoor bar where you can have a cocktail on the hull of a boat and admire the vessels of other seafarers docked in the marina.
If you’re renting a house or even looking for a quick lunch or breakfast option, visit Marie Eiffel Market downtown for take-out or eat-in. Authentic French-press coffee, made-to-order omelets and sandwiches, fresh-made chips and shoestring fries are all delicious, but if you can get there early for the pastries, you’ll think you’ve died and gone to France. They sell out quickly.
Where to Shop
Ram Design Home is a gorgeous shop and interior design firm on North Ferry Road where you can find select home décor items and artwork. Visitors clamor each year for local artist Kiki Boucher’s annual Shelter Island Poster, but you can also find handmade ceramics by Michelle Currier, abstract wall art by Erica Hauser and authentic Makun pillows. Design services from Ram Design Home are by appointment only.
Beachside keepsakes depicting the island are a must-have for vacationers, but Bliss Department Store isn’t your average beach shop. Fifty years and three generations later, the same family still runs the store, and you can feel the heart of this mom-and-pop still beating strong. Tee shirts and swag are just the beginning of the items you might find here, including essentials for those who forgot to pack socks and underwear, and Dockers for those who decide to schedule an impromptu golf game at Goat Hill, the public course at Shelter Island Country Club. The sweatshirt Shelter Island throw blankets are a customer favorite and prove cozy on chilly evenings around the fire pit.
Pure Soul, which has a sister location in Old San Juan, Puerto Rico, is run by owner and designer Sylma Cabrera, a former design director for luxury brands like Saks Fifth Avenue and Christian Dior, among others. The resort-inspired boutique has a selection of unique bags, jewelry, beauty products and clothing hand-picked with a luxurious, cross-cultural lifestyle in mind.
For the Kids
The kids will love spending an afternoon at Shelter Island Whale’s Tale, and on a hot summer day, their shady mini golf course and Hershey’s ice cream bar are just the ticket to keeping cool. A small arcade room and large outdoor terrace also make it ideal for get-togethers with friends and family.
Sylvester Manor
For history buffs, Sylvester Manor provides a unique opportunity to understand Shelter Island’s history, and it’s an up-close look at the 1810 Windmill, which you’ll drive by as you travel the island. The manor frequently is the site of concerts and cultural events, when you can bring a picnic and listen to live music.
Crescent Beach
The largest public beach on the island is Crescent Beach also known as Louis Beach. It’s a strip of sandy beach in Shelter Island Harbor. The water is lake-level calm like many of the beaches on Shelter Island. The beach gets crowded because it’s the most prominent one on the island and has lifeguards, so if you plan to buy a day pass to park, do it early. The Sunset Beach Hotel is across the street, and you can dine there for lunch or dinner, or pop over to the bar for cocktails. It’s a lively setting with a vintage and European vibe.
For Wine Lovers
There aren’t too many people who make it out east on the island without a stop at one of the many vineyards, but did you know you can do a tasting right on the island? Stop by White Oak Farm and Gardens, a beautiful garden décor destination, wine shop and tasting room. Winemaker Tom Spotteck (of Lenz winery on the North Fork) and White Oak Wines owner Kristian Clark team up for a selection of boutique wines by local makers that you can taste and buy. White Oak Wines is known for their rosé. The property holds special seasonal events, like the “Oak-toberfest” coming up Saturday, October 22, at noon.
