Ever since Amerigo Vespucci inadvertently gave his name to 2 continents, people have been dotting improbable names all over maps of the New World. That’s how some of America’s most historic cities ended up sharing names with charming English hamlets and long-abandoned metropolises.

There are some outstanding places to visit that lent their names to famous cities in the United States. Those namesakes offer a great way to learn what was on the minds of those early American settlers. Discover the charm and grandeur of the cities that inspired a nation.

York, England

The Shambles, York

If you had to pick the city whose name you’d adopt for America’s most venerable metropolis, York wouldn’t be a bad choice. Founded by the Ninth Legion back in 71 AD, it’s been a center of English commerce and industry ever since. Not to mention, it’s one of the best-preserved medieval cities in Europe. There’s no shortage of things to do in York that show off the city’s historic grandeur, and you can learn how it hosted a cast of characters that ranged from Constantine the Great to Guy Fawkes.

You can pick up a sightseeing bus pass to explore one of the great historic English cities at your own pace. Don’t miss the spot where Constantine was proclaimed Emperor of Rome, or the charmingly haphazard neighborhood of the Shambles. Or, you can strike out to explore the Yorkshire Dales and see the manor houses and pastoral scenery that probably could have inspired Long Island.

Boston, England

St. Botolph's Church in Boston, England

An old port city that was one of the country’s prime centers of trade, Boston’s name fit so perfectly with its counterpart in Massachusetts Bay that the pilgrims didn’t even bother putting “New” at the front. A visit to Boston, England shows you a charming market town where medieval landmarks still stand along the modern thoroughfare of John Adams Way—which, yes, is named for the president.

You can stop by the 700-year-old Boston Guildhall to check out a free museum showing Boston’s days as a center of international trade, or visit the memorial to the Pilgrim Fathers, who left England 400 years ago in search of religious freedom. And you can visit St. Botolph’s Church, one of the tallest medieval towers in England—and learn the story of its vicar, John Cotton, who encouraged many Bostonians to emigrate in the early 1600s and gave the city a lasting legacy in the New World.

Orléans, France

Orleans, France

A center of commerce and culture with all the charm and beauty you’d expect from one of the great historic cities of France, Orléans was the natural choice to lend its name to French Louisiana’s most important settlement. A trip to Orléans in France lets you explore one of the most prosperous cities in medieval France, with a wealth of medieval and Renaissance heritage less than an hour’s drive away from Paris.

The attractions in Orléans tell the story of a city that’s been at the crossroads of history ever since Julius Caesar leveled it in his Gallic campaigns. Visit the university halls where John Calvin and Molière once studied. See the grand 18th-century manor built for the Duke of Orléans. Head to the museum where Joan of Arc stayed while saving the city from an English siege.

Toledo, Spain

Toledo, Spain at night

The fact that a group of Ohio settlers with no particular connection to Spain chose to name their city after Toledo says a lot about the old city’s stature. This was the capital of the Visigoths and a focal point for Jewish and Islamic history in Medieval Europe. There’s a lot of grandeur on display in a small and scenic area as you explore this historic city. You can find plenty of things to do in Toledo that show off its rich cultural heritage.

Toledo’s location in the heart of Spain makes it the perfect destination for a day trip from Madrid. There’s plenty to keep your attention if you’d like to stay for a while, too. Try out a range of tour options to get to know the best of the city. You can see the windmills that inspired Don Quixote and ride a zipline over the Tagus River while you’re at it.

Memphis, Egypt

Saqqara Necropolis in Memphis, Egypt

Andrew Jackson and his co-founders clearly didn’t lack for ambition when they got the chance to name a city. One of the oldest, most historic cities in the world, Memphis has nearly 4,000 years of memories resting on the banks of the Nile. Even in ruins, the modern-day site is home to some of the most storied relics in the history of civilization. So there’s no shortage of incredible sights to see in Memphis.

You can find plenty of ways to explore some of Memphis’ best-kept relics. Join a private tour to visit some of the oldest monuments in the world, including the 4,700-year-old pyramids in the necropolis at Saqqara, along with the giant 3,200-year-old statue of Ramesses the Great. While you’re in the neighborhood, you can check out the artifacts and exhibits dedicated to Memphis’ heyday with a tour of the Egyptian Museum in nearby Cairo and add in a visit to see the Great Pyramids of Giza.

A New World legacy

Memphis Pyramid and Bass Pro Shops, Memphis, Tennessee

Naturally, even the United States’ most historic cities haven’t been around as long as the places that they’re named for. But it’s still been an eventful few centuries. If you’re looking to explore history and heritage in the New World, here are a few good places to start:

The world has plenty more cities whose names inspired American settlers. (For instance, Rome, Troy, and Delhi all have namesakes in the state of New York.) So what’s your favorite destination with a certain familiar name?