Eight days city-hopping in New England with Jihane

America is home to some of the prettiest road trips in the world – routes that many of us have been lucky to take for ourselves. Here, we’re looking back to 2019, when a member of our London team set off on a weeklong jaunt from Boston to Maine and back to Cape Cod. This is Jihane’s story. 

Words by Jihane 

It seems like it’s been years since I was dreaming up my route through America. Do I take the East to West route, set off up Highway 1, or pass through some of the most stunning landscapes on the East Coast? Of course, within each of those options lie the countless decisions on which cities to stop in, where to veer off for the inevitable road trip photo opp and what roadside hole-in-the-wall restaurant that I absolutely can’t miss.

From London to Boston

After months of planning with my family, this past summer it was finally time to depart on a week-long trip. Most of the travel was done by car but for a few extensions of the trip we used air travel so that we could make the most out of our jam-packed itinerary. The first stop: Boston.

It’s a direct flight from London and has been top on our list of American cities to get to, so naturally, we landed here first. The city is steeped with history from its museums, wide-open parks, or cozy restaurants – all within walking distance of each other.

History at every turn

Walking down the cobblestone filled streets, passing the rows of brownstones and old-style English pubs, you get a sense of just how special this city is. Follow the Freedom Trail to learn more about the city, a 2.5 mile red line taking you to 16 historic national sites. Every twist and turn will tell you more of the American Revolution and is an experience you shouldn’t miss.

You’ll also pass a lot of restaurants and outdoor markets on the trail, but definitely make a point to try North Square Oyster (famed for their seafood plateau) and The Warren Tavern. Located in the oldest public square in America (once Paul Revere’s home), North Square Oyster serves up a seasonal menu based on the availability of fresh seafood and local ingredients.

Inspired? Time to talk to one of our experts about your own trip

Inspired by Jihane’s trip? Follow in her footsteps to set off on a coastal road trip that you’ll never forget.


However, there’s really nothing like catching your own fresh seafood straight from the ocean. The next day, we departed for lobster fishing and spent most of the visible daylight out to sea, looking back on the port of Boston in the horizon. If you are a crab, lobster or seafood lover you’ll want to spend a few days in Boston before boarding a plane and heading up to Maine.

National Parks, seals, and puffins

We then boarded a flight for Bar Harbor where we spent two nights in the middle of Acadia National Park, where you’ll find woodlands, rocky beaches and glacier clad peaks in the distance. There’s nothing like waking up with coffee in hand and watching the fog rise over the horizon and dust over miles of beautiful wilderness straight from your bedroom.

That morning, we walked down to the harbor, boarded our cruise around the island of Bar Harbor and spent the day spotting seals and puffins. This was my son’s favorite activity of the whole trip and we probably could have spent the rest of our time on the east coast counting the marine wildlife swimming by.

The wakeup call the next morning came all too quick as we departed on our road-trip. We encountered wide open views of the ocean and stunning landscapes sprinkle the coastline all the way to Kennebunk. It’s inevitable that our windows were rolled all the way down, radio turned up on blast and noses high in the air, breathing in the fresh breeze rolling right off the ocean. It’s about a three-and-a-half-hour drive to Kennebunk, which I highly recommend for those traveling with kids. From there, head all the way down to Providence, a city like Boston that has a touch of the Old World with its historic buildings and walking tours that will take you back int time.

We ended the trip with Nantucket, Newport, and Cape Cod – a fantastic destination trio in terms of beach and atmosphere with lots to see and do. To name a few: history and bike tour of Nantucket, cliff walking tour in Newport, and a culinary journey in Portland. Though, sailing on America’s cup racing yacht was the icing on the cake (my husband and I both are giddy about America’s Cup and follow it closely). The last couple of nights we spent at the White Elephant, a charming harborside hotel, and then it was back to London via Boston.

Read more about this journey in our new itinerary here.

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