Lucky in Love: Boston, Massachusetts
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From New York to Boston
From Manhattan to the old streets of Boston, with coastal New England in between.
On Lucky in Love, Sophie and Anna hand each day's planning to a coin toss. One of them makes the pick, and the other goes along. This trip is built the same way, and it covers the stretch of the Northeast between its two biggest cities. You start in New York City, then drive north along the coast through Connecticut, Rhode Island and Cape Cod to Boston. Every stop is a choice between harbor and history, and you make the call. The link below opens the full trip, and you can change any part of it.
Start With the Big City
You land at JFK and take a private transfer to the Cambria in Chelsea, a Manhattan neighborhood on the west side with galleries, restaurants and the High Line park close by. The New York City Pass covers the headline sights, so you can move between them without buying tickets at each door. A guided walk through Soho, Greenwich Village and the Meatpacking District shows the city at street level, with cast-iron buildings, cafes and cobblestones. Leave a day open for Central Park or a museum, and treat the city as the warm-up before the driving starts.
Gillette Castle is as interesting as it is eerie.
Drive the Coast Slowly
Once you pick up the car, the pace changes. The road heads north from New York to New Haven, then turns inland for a detour to Gillette Castle State Park. The stone castle was built in the early 1900s by the actor William Gillette and stands on a hill above the Connecticut River, with views out over the water. Back on the coast, Mystic is a small seaport town built around its maritime history, and a good place to walk the waterfront before the road continues east.
From Newport, the route crosses into Massachusetts and reaches New Bedford, a working fishing port with a long whaling history. Beyond it lies Cape Cod, a hook-shaped peninsula that juts out into the Atlantic. The Cape Cod National Seashore, a protected stretch of coastline along its outer shore, gets a free day of its own, with plenty of time for long beaches, dunes and lighthouses. The route then goes on to Boston by way of Plymouth, where the Pilgrims settled in 1620. Each stop is sized for a half day of looking around, with harbors, lighthouses and seafood shacks to fill in the gaps.
You’ll love exploring Boston’s famous Acorn Street, located right next to the Freedom Trail!
Finish in Historic Boston
The trip ends in Boston, one of the oldest cities in the country, and the Harborside Inn puts the waterfront within walking distance. With the Boston City Pass, you can follow the Freedom Trail, a red-lined path through the city that links Boston Common with Bunker Hill and the sites of the American Revolution.
Lunch in the North End is a good break from history. The neighborhood is full of Italian bakeries and narrow brick streets. Lastly, a guided tour of Harvard rounds out the stay and shows the university the way the people who study there see it.
The link below opens the full itinerary, with hotels and car rental included. Flip the coin and pick your days.
From New York to Boston
From Manhattan to the old streets of Boston, with coastal New England in between.
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