• A Crash Course in Painting, Sculpture, and Architecture: Tuscany and Umbria are stuffed with the planet's best art and architecture -- from frescoed chapels to giant civic paintings that date back 700 years -- and every turn of the corner reveals a new wonder in paint or stone. If you've ever had any curiosity about what it all means, you've just landed in the best place in the world to learn.

  • Hiking the Hills of Florence: The walk from Florence up to Fiesole is famous enough to earn a scene in the movie adaptation of E. M. Forster's A Room with a View (even if they cheated and took carriages). But don't neglect the hills of San Miniato and Bellosguardo that rise south of the Arno; the views over the city here are closer at hand, and the land is less developed.

  • Biking Lucca's Walls: The elegant Republic of Lucca is still snuggled comfortably behind its 16th-century walls, ramparts so thick they were able to be converted into a narrow city park -- a tree-lined promenade running a 5km (3-mile) loop around the city rooftops. The bicycle is the preferred mode of transportation in Lucca, and you'll be in good company as you tool under the shade past parents pushing strollers, businessmen walking their dogs, and old men at picnic tables in their 40th year of a never-ending card game.

  • An Evening Stroll in Perugia: Perugia's wide Corso Vannucci is perfect for the early-evening stroll Italians everywhere turn out for -- the passeggiata. It's the time to see and be seen, to promenade arm in arm with your best friend dressed in your best duds. The crowd flows up the street to one piazza and then turns around and saunters back down to the other end. When you tire of meandering, take a break to sip cappuccino and nibble Perugia's fine chocolates in one of the classy cafes lining the street.

  • Going Off the Beaten Path in Assisi: Who would've thought you could find a primal Umbrian country experience in overtouristed Assisi? Save the basilica's frescoes for the afternoon and get up early to hike into the wooded mountains of Monte Subasio to St. Francis's old hermitage. After a morning spent in contemplation with the monks and wandering the state parkland, head back to Assisi, but be sure to stop a mile outside town for a big lunch at La Stalla, one of the best countryside trattorie in central Italy.

  • Getting Into Hill Town Life: Panoramic views, cobblestone squares, friendly cafes—these are the charms of everyday life in a Tuscan hill town, ready to be savored in Cortona, Montepulicano, Volterra, San Gimignano, and Montalcino.

  • Fresco Gazing In Siena: Two masterpieces of medieval art bring the past to life in Siena: Ambrogio Lorenzetti’s “Allegory of Good and Bad Government,” in the Palazzo Pubblico, and depictions of the healing arts by Domenico di Bartolo and others in the former hospital Santa Maria della Scala. Linger over their storytelling scenes—the characters seem to reach across the centuries and speak to us.

  • Basking In Some Of The World’s Most Beautiful Landscapes: Open your senses to the beauties of the Tuscan countryside as you drive through the famous Chianti vineyards between Siena and Florence, or along the meandering roads of the Val d’Orcia between Pienza and Montalcino.

  • Enjoying Fine Wines: You’ve seen the vines; now sample the wines. Tuscany’s bounty, of course, includes famous Chianti, Brunello di Montalcino, and Vino Nobile di Montepulciano, but don’t stop there—almost every town has its own trademark vintages, from San Gimignano’s Vernaccia to Cortona’s Syrah.

Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.