A Skipper’s Welcome: Sailing Into Stonington, Connecticut
And spend a restful night at the most romantic inn along the New England shoreline
By Bill Griffin, owner of the Inn at Stonington
There are mornings on the Inn’s back porch in Stonington Borough when I catch myself pausing mid-coffee.
Out past Water Street, the harbor is doing that thing it does when the light comes in low, and the lobster boats are already halfway to their traps.
That’s when I remember – there is no better stretch of American coastline to drop a lunch hook in.
I’m Bill Griffin, owner of the Inn at Stonington, New England’s most romantic shoreline inn.
My guests arrive by car, by ferry, and more often than you’d think, by sail.
After three decades of pouring coffee for captains in this little village, I can tell you the real magic of southeastern Connecticut happens the moment you swing the dock lines off and head for open water.
Stonington Harbor: A Dock with a Past
Stonington Harbor isn’t just a pretty natural anchorage – it’s Connecticut’s easternmost cruising port and the only one with a real taste of the Atlantic working its way in.
Forty-four slips at the municipal marina welcome runabouts, trawlers, and proper yachts alike, and the protection of the breakwater makes it feel almost inland – until a swell rolls through and reminds you exactly where you are.
From the inn, I can watch the Stonington Harbor Yacht Club come alive in the morning.
Members have been gathering here for over two decades, and the club maintains a remarkable network – more than 75 reciprocal relationships with yacht clubs around the world.
But the real gift, as any of our cruising skippers will tell you, is the reciprocal handshake that stretches from one end of the Sound to the other.
Pull up your burgee at the SHYC dock, and you’re treated like family from Noank to Port Washington.
The Picnic Stop: Sandy Point, Watch Hill’s Quiet Neighbor
For lunch, my favorite run is south and east out of the harbor and into Little Narragansett Bay.
There’s a place we locals call Sandy Point – a thirty-five-acre barrier island, mostly in Westerly, Rhode Island, and partly in Stonington, Connecticut.
It is the closest barefoot island to Watch Hill you could ask for – sitting roughly a mile and a half north-northwest of Napatree Point – and it almost feels as if it were put there for sailors with wicker hampers and a thirst for quiet.
What makes Sandy Point special is what it doesn’t have.
There are no buildings to ruin the horizon, no road access, no loud concessions.
The Avalonia Land Conservancy keeps it wild.
Pack a bottle of something cold, a wedge of cheese from a shop in Stonington Borough, a loaf from one of our bakers, and drop the hook on the lee side.
A swim, a stretch on the sand, the open sky over the Sound – that’s a Stonington afternoon, uncomplicated.
When guests at the inn want to combine a sail with a stroll ashore, I’ll send them back up the hill to Watch Hill afterward.
The Watch Hill Yacht Club has been part of this coast since 1913 and stands ready to welcome reciprocal members.
A short walk up Bay Street brings you to the carousel, the boutiques, and one of the prettiest sunset overlooks in all of New England.
The Cut: A Two-Mile Squeeze Worth Every Minute
The sail I most love to recommend to guests is the one that takes you through The Cut – the privately marked channel that threads between the tip of Napatree Point on the Rhode Island mainland and the eastern shore of Fishers Island, New York.
It is a tight, beautiful two-mile squeeze – Fishers Island sits a tick over two miles offshore from Napatree Point (Fort Mansfield) – where Fishers Island Sound opens to the south, and the current can run close to two knots at the change of the tide.
Back in the day, The Cut was a working channel for oystermen and freight boats running toward Block Island.
Today it’s a quiet rite of passage for anyone who wants to say they’ve properly cruised the eastern Sound.
Line up on the marks, watch the tide setting across your bow, and you’ll pop out the south side with Block Island laid open on the horizon and the Montauk light visible in the distance.
I tell first-timers the same thing every time: respect the current, sound a passing sequence, and don’t be shy about hailing the Fishers Island ferry if you need a hull-up clarification on local traffic.
The harbor masters on both sides of this passage are unfailingly courteous, and that same courtesy is what keeps this piece of coast working like one big, friendly yacht club community.
Reciprocity: A Coast Without Borders
This is the part that surprises new arrivals most.
There’s almost no friction when you cruise between Stonington, Watch Hill, Noank, Mystic, and Fishers Island.
The Stonington Harbor Yacht Club recognizes more than seventy-five clubs globally, and within a single day’s sail you’ll find the same handshake waiting at Watch Hill Yacht Club, Ram Island Yacht Club in Noank, at outposts like the Indian Harbor Yacht Club over in Greenwich, and at places like the Saugatuck Harbor Yacht Club down in Westport.
Most of these arrangements have been quietly in place for generations.
It isn’t just a paperwork relationship – it’s a shared understanding that anyone with a proper burgee on the stern and a polite voice on the radio belongs at the table.
A captain visiting from one of those clubs can pull into our harbor at Stonington, step off the dock, and find the dining room ready and the launch waiting.
Bone of Our Bone: The Whalers Who Built This Town
You can’t really understand the harbor I look at every morning without knowing the men who built it.
Stonington’s story is soaked in whale oil and rope tar.
By the 1830s and on through the mid-1800s, this little village was putting out sealers and whalers with the best of them, and historic Mystic – right next door – launched twenty-eight vessels on a hundred and two whaling voyages in roughly thirty years.
When the seal populations finally gave out mid-century, the Stonington fleet pivoted hard, and our captains were soon sailing right alongside the great New Bedford ships – among them the Charles W. Morgan, the last wooden whaleship still afloat in the world, preserved just up the road at the Mystic Seaport Museum.
You can feel that whaling past in the Borough’s street names and in the old captain’s houses facing the harbor. And envision the Battle of Stonington in 1812.
Many of the families who have welcomed lodging parties at the inn over the years had grandfathers who signalled whales from the headlands and uncles who spent three years at sea chasing the great leviathans below the Horn.
Connecticut ranked second only to Massachusetts in the American whaling trade, and Stonington carried more than its share of that weight.
Come In, Drop the Hook, Sit Awhile
So that’s the invitation I offer anyone who books a room at the Inn at Stonington.
Come for wine and cheese in the evenings and stay for the sailing.
Spend one morning with a chart on your lap over our continental breakfast, then let the tide carry you through The Cut.
Picnic on a quiet stretch of sand where nobody can reach you except by boat.
Tie up at a yacht club where the dockmaster already knows to expect you by your club’s flag.
We’ll have coffee on the porch when you come back in.
The water will be flat, the gulls will be working, and the harbor will look much the way it looked to the whale captains two centuries ago – patient, generous, and ready to send you out again.
We welcome you to the Inn at Stonington, the most romantic inn along the New England shoreline.
Your hosts – Sue, Stephanie, and Bill
60 Water Street, Stonington, CT, 06378
