With equally picturesque water and shore landscapes, Block Island has been a favorite spot of mine since my initial sailing excursion there a few years back. Formed by glaciers that pushed their way down the East Coast ten thousand years ago, the rocky landscapes that make up its shoreline lie 15 miles from Montauk Point, and 13 from the coast of Rhode Island. Though Block Island is reachable via ferry and flight, the true soul of the spot is discovered via boat, preferably under sail. A midsummer opportunity to visit aboard a friend’s 30’ ketch had me packing bags—primarily my camera gear and swim trunks—and lighting out of NYC’s clotted humidity last July.


My plan was rather simple: motorcycle from Brooklyn to Montauk, hop aboard my friend’s boat and sail to Block, then spend a couple of days sunning and exploring before a ferry return to Montauk and ride home.

Yet, unpredictability being one of the charms of sailing, plans changed. Slack winds meant my friend wouldn’t make the trip from Greenport to Montauk in time for my arrival. And our dreams of a brisk sail to Block were forming into a reality of motoring at 4 knots, accompanied by the asthmatic rattle of the onboard diesel. So, improvising, I backtracked from Montauk to East Hampton on the train—riding against the tide of visitors, headed East for a weekend of sunburns and luxury-priced cocktails.

Rendezvousing in East Hampton, we anchored for a calm, damp night in Three Mile Harbor Marina. Shortly after dawn the next day, fueled by propane stove heated coffee, we pushed off into a silent fog, sliding our way into the Block Island Sound. The near-windless trip was long and warm, but well worth it for the experience of dropping anchor in the Great Salt Pond in time for sunset.

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The next morning was set for exploring. We chose to rent the 50cc scooters that pepper the island’s few roads instead of bicycles, opting for convenience over health. Island Moped hooked us up with an early-bird special that provided ample time to cruise without inflicting too much damage to our wallets.

After a slow roll through New Shoreham’s downtown, was the BI Southeast Lighthouse and Mohegan Bluffs. Since 1875, the lighthouse has stood atop the 150 foot clay cliffs which tumble oceanward. Corn Cove, reached via an elaborate series of wooden steps, provides a beautiful, private, if rather rocky, spot to spend the day swimming and admiring a continuously-growing collection of visitor-built cairns. Dinner was spent in sleepy, post-sun daze at the excellent Eli’s Restaurant, which garners extra points for a full, delicious vegetarian menu.


The next day passed in a similar, if even less ambitious, way. Breakfast gluttony was secured from Payne’s, home of the self-proclaimed “killer donuts.” While piloting the dingy back to the boat, we discovered a beaching area where we could leave the boat and wander across a small path through the dunes to Fred Benson beach. Ocean dips, people watching and chilling was broken only by an excursion for tacos at Los Gatitos, the Mexican food deck dining option from the folks behind popular nightspot Yellow Kittens Tavern. Dinner was cooked on the boat, accompanied by one of the most jaw-droppingly beautiful sunsets I’ve ever seen. Not a bad ending to a visit to a little summer paradise.


To get here, ferries run from daily to/from Montauk and points in RI and Mass. Flights, which take a whopping 12-minutes, depart from Westerly, RI. While on the island, stay at the iconic Surf Hotel, built in 1876. Or check out various options via Airbnb. But nothing beats sleeping on board a boat, so make some friends!