Fleas are responsible for the charm that draws admiring visitors to Siena. That’s because the damage they caused back in 1348 left the city crippled, unable to change, and stuck in the Middle Ages. The dreaded Black Death, brought by flea-carrying rats, struck Europe’s crowded cities and decimated entire populations. Half the people of Siena died. Unlike Florence and Milan, the city never recovered its former glory. What that means for tourists today is a city that looks as it did centuries ago, with medieval architecture and magnificent art. And, now it’s combined with Italian gusto and a Sienese flavor all its own.

The heart of Siena is the shell-shaped Piazza del Campo, where everyone comes to drink espresso and eat gelato at sidewalk cafes while watching the world go by. Twice in the summer, crowds gather to watch the Palio, the exciting, historic horse races sponsored by the various contrada, or neighborhoods. On one side of the Campo is the City Hall and Tower. There’s an interesting museum here and, if you climb the 300 steps to the top of the tower, fantastic views of the Tuscan landscape. From the Campo, narrow streets, alleyways and steep steps wind past quaint buildings and landmarks.

One of Siena’s major attractions is the Duomo, a Baroque cathedral that is amazing. Striped marble, inlaid mosaics, gilt carvings, frescoes, statues – they’re all here, and not to be missed. You can rent an audioguide, useful for understanding some of the array before you. Across from the cathedral is Santa Maria della Scala, a museum that was once a hospital. The frescoes show what health care was like in the 15th century (better than you might think).

There are numerous other churches and museums, and a theater where you can watch a brief film on the history of the Palio. It gives the flavor of the wild drama and ritual around the traditional horse races. This university town also offers numerous concerts and cultural events. When you want to tour the Tuscan countryside, try something different: the Nature Train. The old-fashioned train travels through some of Italy’s most beautiful land, the hills of Tuscany. Rides are available on Sundays, May through October.

One of Siena’s most pleasant hotels is the pricey Palazzo Ravizza, which I love for its garden. It has hand-painted tiles and local marble in the bathrooms, traditional furnishings, and sketches of travelers from past eras. The formal garden, overlooking the Tuscan olive trees and vineyards, is a wonderful place to relax after a day of sightseeing.
Villa Elda, less expensive, is a 10-minute walk from Piazza del Campo. It has 11 rooms and an Art Nouveau atmosphere and is another fine lodging choice. There’s a rooftop terrace as well as a garden.
For some good Sienese restaurant ideas, take a look at Recommendations for Tuscany Restaurants.