San Gimignano
San Gimignano is a charming hilltop town best known for its towers. While only 14 of the original 76 towers have survived to the present day, San Gimignano’s skyline is still one of the best preserved in all of Tuscany. The Gelateria di Piazza in the Piazza della Cisterna (Square of the Cistern) is well-worth the pilgrimage; the gelato has won multiple world-wide ice-cream competitions. If you need to work up an appetite before consuming mass quantities of gelato, consider climbing the nearby Torre Grossa. The view of the surrounding Tuscan countryside is spectacular.

Siena
Although the city declined after the Black Death in 1348, Siena was Florence’s main rival in the thirteenth and early fourteenth centuries. The city is divided into seventeen contrades or parishes. The height of civic life is the Palio, a horserace that takes place every year on July 2nd and August 16th in which the seventeen contrades compete against one another. Even if you will not be in Siena for the Palio, the expansive Piazza del Campo, zebra-striped Cathedral, and winding, narrow lanes make Siena a must-visit stop in Tuscany.

Lucca
Lucca is famous for the brick walls that enclose the city. The walls were built in the sixteenth and early seventeenth centuries and are the best-preserved defensive walls in Tuscany and, arguably, in all of Europe. Cars are not allowed in the city center but because the streets of Lucca are flatter than those of other Tuscan hill towns, the locals use bicycles as their primary mode of transportation.

Wine, Olive Oil and Cheese Tasting
The majority of Tuscan wines are made from the Sangiovese grape. The best known varieties are: Chianti Classico (look for the black rooster on the label), Brunello di Montalcino and the Vino Nobile di Montepulciano. A sheep’s milk cheese known as Pecorino is an excellent companion to the Tuscan wines. Aged Pecorino stands up well to the more robust Tuscan wines. Olive oil tasting may seem a bit odd; the reassuring news is that you taste the oils on pieces of Tuscan bread rather than by sipping it. You will be surprised at how different various olive oils can taste and probably will leave with a greater appreciation for first-cold-pressed, extra-virgin olive oil.

Bike Ride
Even if you don’t have a bicycle to ride around in the city center of Lucca, you should consider exploring the Tuscan countryside by bike. You can rent bicycles in many of the towns or there are several companies that run bicycle tours.