242 miles SW of London; 161 miles SW of Southampton

“It’s seen better days”—if ever a town fit that cliché, it’s Plymouth. Historic and once-beautiful, Plymouth was founded in the 11th century and grew to become the principal seaport of Tudor England. All the known world sailed here and walked its narrow medieval streets. Few places in the south of England are as rich in romantic lore.

Sadly, most of that old Plymouth has gone. German bombing raids during World War II all but devastated the city; as many as 75,000 buildings were destroyed. Whatever the Nazis didn’t destroy, spectacularly bad development in the 1950s and ‘60s did. Huge swathes of the city were replaced with oppressive, brutalist concrete buildings. Today, Plymouth is the kind of city that one passes through and winces at the thought of how good it must once have looked.

However, not all the historic old town was lost. The Elizabethan section, known as the Barbican, contains many original buildings, and a few good sights relating to the first Pilgrim Fathers who colonized America. The Mayflower and Speedwell, which sailed from Southampton in August 1620, docked into Plymouth after suffering storm damage. The Speedwell was abandoned; the Mayflower made the trip alone. The next stop from here was the New World.

In Britain, Plymouth is more associated with its most famous son, Sir Francis Drake—the swashbuckling admiral and one-time favorite of Queen Elizabeth I, who fought off the Spanish Armada in 1588. Legend has it that he was playing bowls up on Plymouth Hoe (a stretch of cliff overlooking the bay) when a messenger galloped over to tell him of the impending invasion. “There is plenty of time,” he is said to have replied, “to finish this game and beat the Spaniards.”

Unless you’re a Tudor history buff, there is little to detain you in this workaday town. The Barbican is interesting, and its historic sights impressive—but not impressive or plentiful enough to warrant more than an afternoon’s detour.