This Tuscan hill town will transport you back to the Middle Ages. Siena's grand cathedral, built in the 1200s, has treasured artworks and marvellous marble floors. The Piazza del Campo, the main town square, is a UNESCO World Heritage Site. It's also home to the Palio, perhaps the most infamous horserace in the world. No goofy hats and mint juleps here—this is a mediaeval tradition involving bareback riders racing on cobblestones (so as you might imagine, it's quite dangerous). Siena is an easy daytrip by train from Florence, just 43 miles away.

This picturesque Umbrian city has a history that spans many eras. The city wall and arch are Etruscan; the sixth-century Sant'Angelo church was built atop a Roman temple; the town's cathedral is both Gothic and Renaissance. If you have a sweet tooth, visit the famous Perugina chocolate factory; if you have a full set of sweet teeth, visit during the Eurochocolate festival, held in October, when the entire town reportedly smells of chocolate.

Centrally located Umbria's principal cities include Spoleto, Assisi, and Terni. The capital, Perugia, is famed for its chocolate. Take a tour bus or prepare for daredevil Italian drivers if you opt to rent a car. Assisi's Basilica has a host of treasures, including works by Giotto. The town is also home to the crypt of St. Clare, patron saint of television. St. Francis' meditation retreat is in the mountains to the north. Classes at Velia's Cooking Style in Terni make good use of local produce.

Getting its name from the medieval Duchy of Limburg (now split among Holland, Belgium and Germany and the birthplace of the infamously pungent Limburger cheese), Limburg is the Netherlands’ southernmost region. Many of the area’s best attractions are concentrated in the capital of Maastricht, but other sights include the 12th-century Valkenburg castle ruins, the 17th-century Eijsden castle, the 20th-century Glaspaleis (built next to a medieval church at Heerlen), and De Meinweg National Park.

A spot of white in the turquoise waters of the Aegean Sea, the island of Naxos is a unique blend of ancient ruins and beach culture. The largest of the Cycladic Islands, Naxos is the childhood home of none other than Zeus, king of the gods. Upon arrival in Naxos, hike over a causeway to Palatia, where the Portara, a stone gateway to an ancient temple that no longer exists, stands alone, the symbol of the island. At sunset, the views of the island, and the sea beyond, are breathtaking.

With its collection of historic homes, museums and battlefields, Frederick, Maryland, is a must-see destination for any history enthusiast. The sites of two bloody Civil War battles are preserved at Monocacy National Park and South Mountain State Park. Within the city, visit the National Museum of Civil War Medicine and learn how soldiers wounded in those battles were treated, or visit the house of Barbara Fritchie and picture her hanging the Stars & Stripes in defiance of the Confederate Army.