Embark on an unforgettable passage from the iconic skyline of New York City to the rugged coastlines of Newfoundland. This high latitude adventure combines exhilarating offshore sailing with landfalls at some of North America’s most historic maritime towns and beautiful coastlines. Along the way, you’ll hone your skills at sea, work as part of a watch system, and experience the thrill of true bluewater sailing. On such an adventurous route, the exact itinerary will differ everty time as the widn and weather dictate where we can stop. Here is a rough outline of highlights along the way.
Departing New York City
There are few sailing departures as dramatic as slipping lines in downtown Manhattan. You’ll step aboard in the heart of New York, stow gear, and complete a thorough safety briefing, including practice with lifejackets, harnesses, and cold-water immersion suits. With everything secure, we cast off and ease down the Hudson River. The city’s skyline towers above us, a canyon of glass and steel. The Statue of Liberty comes abeam and then its under the Brooklyn Bridge. Ahead, the East River carries us past Governors Island, the Upper East Side, and the barbed-wire outlines of Rikers Island before we push out into the wide waters of Long Island Sound.
Long Island Sound
The 110-mile reach of Long Island Sound is one of the busiest and most beautiful waterways on the U.S. East Coast. To the north lie the wooded shores and historic towns of Connecticut – Mystic, New Haven, and New London – each with a long maritime history. To the south stretch the beaches and palatial estates of Long Island’s “Gold Coast,” once the summer playground of America’s industrial titans. We’ll sail past old lighthouses, navigate tidal rips, and, if conditions allow, drop anchor in Oyster Bay. This sheltered inlet was home to President Theodore Roosevelt at Sagamore Hill, and it makes for a perfect first night away from the city. From here, we may make a longer overnight passage of 150 nautical miles to push north, settling fully into the rhythm of life at sea.
Newport, Rhode Island
Few places encapsulate America’s maritime spirit like Newport. This handsome seaside town hosted the America’s Cup from 1930 to 1983, and its harbours are still filled with classic sailing yachts, working lobster boats, and racing fleets. Approaching from the ocean, we sail past the dramatic cliffs and Gilded Age mansions of Bellevue Avenue, built by families like the Vanderbilts and Astors as their “summer cottages.” Ashore, Newport’s cobblestone streets are a mix of colonial architecture, bustling wharves, and a lively waterfront lined with seafood shacks, galleries, and chandlers. For sailors, Newport is a pilgrimage site – a living museum of yacht racing history and seamanship.
Martha’s Vineyard & Nantucket
Just beyond Cape Cod, two islands embody the romance of New England sailing. Martha’s Vineyard has wide, dune-fringed beaches, oak forests, and the colourful “gingerbread cottages” of Oak Bluffs – remnants of the 19th-century Methodist camp meetings. Farmers’ markets are full of local produce, and harbours fill with classic wooden sloops and catboats. A few hours’ sail further east is Nantucket, once the whaling capital of the world. Its cobbled streets, grey-shingled houses, and historic lighthouses make it a living postcard, while its bustling centre boasts boutiques, bookshops, and some of New England’s best seafood. Both islands allow you to soak in the coastal history and enjoy a taste of seaside culture before we turn north into open water.
Offshore Passage to Nova Scotia
From Cape Cod, we strike out on a 350-mile passage into the North Atlantic, usually just under a three-day sail depending on conditions. Now the yacht becomes our world. We stand watches through day and night, adjusting sail trim to the wind and weather we face. The prevailing south-westerlies can provide fast, exhilarating sailing, though weather in this part of the ocean is famously changeable, demanding good teamwork and vigilance. It’s the perfect stretch to improve your offshore skills and enjoy the magic of open ocean night sailing under the stars. Wildlife sightings are frequent – pods of dolphins, shearwaters skimming the waves, and as we push further north, minke and fin whales may be surfacing alongside.
Landfall in Nova Scotia – Lunenburg
After the passage, the granite headlands of Nova Scotia rise over the horizon. We likely make our landfall at Lunenburg, a UNESCO World Heritage Site and one of the most beautifully preserved wooden towns in North America. Founded in 1753, it still boasts around 70% of its original colonial buildings, painted in striking shades of red, yellow, and blue. Once ashore, we can stroll the waterfront boardwalk, watch wooden schooners being restored at the historic shipyard, or visit the Fisheries Museum of the Atlantic. This is also the birthplace of the famous Bluenose schooner, a Canadian icon that once dominated the international racing scene.
Across the Gulf of St Lawrence
A passage of around 250 miles now takes us across the Gulf of St Lawrence – one of the richest marine ecosystems on the planet. Here, the cold Labrador Current meets warmer waters from the south, creating nutrient-rich upwellings that attract whales, seals, and vast flocks of seabirds. We may encounter humpbacks breaching, minke whales feeding, or even the towering icebergs that drift south from Greenland each spring and early summer. The gulf is also known for sudden fogs and strong tidal currents, which demand precise navigation and sharp watch-keeping – an excellent test of the skills you’ll have been honing throughout the voyage.
The South Coast of Newfoundland
Arriving on Newfoundland’s south coast feels like stepping back in time. With no roads connecting many of its settlements, this is a region where communities like Francois, Ramea, Grey River, and Bay d’Espoir are still accessible only by sea. Sheer granite cliffs plunge hundreds of feet into the Atlantic, waterfalls cascade from high plateaus, and deep fjords cut into the coastline, providing spectacular anchorages. The villages themselves are clusters of brightly painted houses clinging to the rock, where fishing is still the mainstay of daily life. It is one of the most isolated, dramatic, and rewarding cruising grounds in the world.
Saint Pierre & Miquelon
A short sail off Newfoundland’s southern coast are the French islands of Saint Pierre and Miquelon – the last foothold of France in North America. Here the tricolore flies, euros are the currency, and you can wander narrow streets lined with pastel-coloured houses, bakeries, and cafés that feel straight out of Brittany. The islands have a unique cultural blend: French cuisine and wine meet a rugged North Atlantic setting. This is a rare chance to experience a piece of Europe without leaving the western hemisphere!
Arrival in St Johns
Our journey culminates as we sail along the northeast coast of Newfoundland. We sail past the colourful, steep-sided city of St John’s, the island’s capital, before rounding Cape St Francis – the northern headland that marks the entrance to Conception Bay. From here, the coast is rugged and imposing, with landmarks such as Imfath Rock standing as sentinels above the icy Atlantic swell. Turning south into the broad expanse of the bay, the land begins to soften, with fishing villages and wooded slopes lining the shore. Our voyage concludes at the Royal Newfoundland Yacht Club in Conception Bay, a fitting end to a passage that has carried us from the skyscrapers of New York to the wild edge of the North Atlantic.
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