Shelter Island guide: Restaurants, hotels, things to do

A ferry ride away, here's how to plan a very long Shelter Saturday on Shelter Island. 

8:30 a.m.: Ferry from Greenport or Sag Harbor

The first — and last — decision to make is yours: which ferry to take, one that may well be dictated by its proximity to your domicile. The North Ferry (631-749-0139, northferry.com) leaves from docks at the terminus of Third Street in Greenport (although lines often begin on Wiggins Street and wind their way toward the boats). Round-trip prices are $24 for a vehicle and driver, $3 each way for additional passengers, for a trip that takes about nine minutes. As for the South Ferry (631-749-1200, southferry.com), it leaves from docks at 400 Ferry Rd. in Sag Harbor, and round-trip prices are $20 for vehicles, $3 each way for passengers (both in-vehicle and walk-on), for a trip that takes about five minutes. Both ferries are cash or check only, and neither takes reservations. 

9 a.m.: A breakfast for the ages

Wherever you land, there’s something apropos about starting your journey at the distinctly North Forkish Shelter Island Heights Pharmacy (19 Grand Ave., 631-749-0445). Maybe it’s the ancient general-store vibe, or the antediluvian lunch counter, where locals congregate daily to catch up on gossip and scan the Shelter Island Reporter’s exceptionally thorough and entertaining police blotter ("To avoid hitting the deer, she hit a tree, damaging the right front bumper and quarter panel."). But the real draws are the breakfasts and lunches, which the pharmacy has been banging down on its counter for more than 100 years, and there are few things in life more Sheltery than the sight of eggs being fried and spatula-ed onto a paper plate, garnished with bacon and laced with feathery-good hash browns, unless it’s chocolate milkshakes being whirred, or BLT sandwiches stacked skyward at this island original.

11 a.m.: Picnic provisions

There’s no getting out of it — you’re going kayaking today. The rowing is allegedly novice-level, and your destination is . . . well, more on that later. No proper kayaking experience is complete, apparently, without the traditional gathering of enormous amounts of picnic provisions and stuffing them into every part of a boat’s cockpit not otherwise occupied by one’s legs. One North Forkish place that stands more than ready in this regard is Sylvester Manor Farmstand (21 Manwaring Rd.), which stocks lots of fresh produce, snacks like North Fork potato chips and beautiful bouquets of wildflowers, bringing a romantic touch to every picnic blanket.

Those who like their picnics premade might head to Maria’s Kitchen (55 N. Ferry Rd., 631-749-5450, mariaskitchenshelterisland.com), which, although it specializes in Mexican plates, offers a robust selection of eat-and-run items, including wraps, quesadillas and chicken salad sandwiches on a roll.

Noon: Postpone kayaking

We said you had to go kayaking, but not that you had to go this second. Why not stall for time — in style — at The Terrace restaurant and bar at Pridwin Hotel and Cottages (81 Shore Rd., 631-749-0476, caperesorts.com), which was spruced up mightily after a 2022 renovation. 

It’s so pretty that some will undoubtedly consider staying the night — where prices this time of year start at $549 for a king guest room — while the rest of us will happily settle for fine mai tais with rum and orange Curaçao, spectacular hillside views of Crescent Beach and its attendant swimwear — as skimpy and statementy as anything they’re hawking on Newtown Lane.

1 p.m.: OK, now you really do have to go kayaking

If you go on just one novice kayak trip this summer, make it the 2½-mile Coecles Harbor Marine Water Trail, which begins at the exact spot where Kayak Shelter Island (80 Burns Rd., 631-749-1990, kayaksi.com) launches its well-maintained rental kayaks, both singles ($35 for two hours, $50 for four, $65 all day) and doubles ($55; $75; $100).

And those not wishing to spend an entire day on the water should at least make it to Taylor’s Island, which is not to be missed. Privately owned until 1998 and now owned by the Town of Shelter Island, the island features the historic Smith-Taylor Cabin, an Adirondack-style cabin built around 1900 with 1930s additions. 

4 p.m.: Tour a historical haven

Once back on dry land, hang up the paddle and head back to civilization, or rather civility, and the Shelter Island Heights Historic District. A walking tour of the neighborhood, first laid out in 1872 as a religious summer retreat for Brooklyn Methodists and utterly unchanged since, is a folk architecture lover’s fever dream. Every cottage is cuter than the last, all of them adorable relics from a simpler era, with all the gabled roofs, verandas and dollhouse touches the name implies.

5 p.m.: Canoodle with the glamorous set

Dinner at 5 p.m. is verboten on Shelter Island, at least judging by the hordes that descend on the Sunset Beach Hotel (35 Shore Rd., 631-749-2001, sunsetbeach.fun) at that hour. Blessed with an ideal location across the street from Crescent Beach and well- stocked with persimmon-hued deck chairs and flappy yellow awnings reflecting a game attempt at the French Riviera, the hotel (where prices at this time of year typically start at $799 a night) is the spiritual home of the Shelterati, movers and shakers from the Hamptons and beyond.

High-priced cocktails include Gimme Shelter, a chili-salted-rim riot of mezcal, ginger, lemon and pineapple; and St. Tropez limonade, composed of gin, basil, cucumber and lemon. 

6 p.m.: Soak up the atmosphere at a charmer

Continuing your oscillation from highfalutin to low key, you arrive at yet another hotel happily reclaiming its former glory, The Chequit (23 Grand Ave., 631-749-0018, thechequithotel.com), its face-lift completed in 2022. The inn’s 19 rooms located in the main building, which dates to 1872, have all been updated (they start at $525 for a king bed), as has the exterior, spruced up to include everything from hanging egg chairs on the veranda to a lounge with lots of cozy, firepitted areas surrounded by bushy hydrangeas. 

8 p.m.: Enjoy country club digs, no membership required

By this point, you’re no doubt wondering if there’s any spot on Shelter Island that doesn’t lean more North or South Fork by a writer determined to run his conceit into the ground. There is. It’s the 1901 Grill (26 Sunnyside Ave., 631-749-5466, shelterislandcc.org), which underwent a renovation in 2024.  Whether you’re a golfer or not, a Shelter Island Country Club member or not, you are expressly invited to end your trip at the top of Goat Hill, adjacent to the course’s ninth and final hole. 

Thus the Grill, where chef Casey Williams flawlessly executes garlicky-buttery linguine with clam sauce, superb brick chicken with pureed potatoes and more. It is an eatery both no-frills and fancy, upscale and approachable, which is to say equally North and South Fork, right down to the cocktail menu, which features a North Ferry Negroni and South Ferry Spritzer.

By Scott Vogel

scott.vogel@newsday.com

Newsday writer and restaurant critic Scott Vogel aims for a refreshing, gimlet-eyed take on the Long Island food scene, often while drinking a refreshing gimlet.