• Tuscany. We don't promise that you'll ever want to leave.

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  • Winemaking. Age-old traditions are alive and well.

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  • Montepulciano, with a seductive mix of medieval and Renaissance architecture.

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  • Basilica of St. Francis, one of the most important Christian pilgrimage sites in Italy. Assisi.

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  • Paper handmade from rags, as it's been done since the Middle Ages. Bevagna.

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Essential Tuscany & Unexpected Umbria.

 "Topnotch. A wonderful introduction to Italy. Hotels were spectacular—a special thanks!" 

—Nancy & Matthew,  journey to Italy


Head for the hills... of Tuscany and Umbria, that is. Where la dolce vita is the only way to go. Begin in Florence, then into Siena for an in-depth look. Visit San Gimignano, Volterra, magnificent Chianti. Wine-taste in Volpaia, Radda, and Brolio, or Verrazzano and Greve. Montalcino, next, then Pienza, Montepulciano, Perugia, Assisi, Spoleto, Orvieto, and end in Rome.



Type:Custom Journeys


Sample Journey

This is a 10-day sample itinerary. Remember that R. Crusoe can create a Tuscany and Umbria journey of any length to meet your exact specifications.

Day 1: United States
• Overnight flight to Italy.
Overnight in flight
Day 2: Florence, Siena, Italy
• Land in Florence, drive to Siena.
• Siena walking tour including a contrada, Piazza del Campo, Palazzo Pubblico.
• Leisure time.
Overnight in Siena

Day 3: San Gimignano, Volterra
• Drive to San Gimignano, old town tour.
• Volterra old town including Palazzo dei Priori, Palazzo Pretorio, Tower of the Little Pig, cathedral and baptistry, various churches.
• Return to Siena.
Overnight in Siena
Day 4: Chianti Region
• Tours and wine-tastings in Castello de Volpaia, Radda and Castello di Brolio, Rampini Ceramics Factory, or wine-tasting at Castelli di Verrazzano and Greve.
Overnight in Siena
Day 5: Sant'Antimo, Montalcino
• Sant'Antimo abbey, Montalcino old town tour, Fatoria Barbi Colombini or Castello Banfi and Enoteca La Fortezza wine-tasting, or morning at leisure in Montalcino, afternoon touring, wine-tasting at Enoteca La Fortezza.
Overnight in Siena

Day 6: Pienza, Montepulciano, Perugia
• Drive to Pienza (Umbria), cheese-tasting.
• Montepulciano walking tour, Vino Nobile tasting.
Overnight in Perugia

Day 7: Perugia, Assisi
• Perugia walking tour including Piazza IV Novembre, cathedral, Rocco Paolina fortress.
• Assisi Basilica of St. Francis.
• Return to Perugia.

Overnight in Perugia

Day 8: Spoleto, Bevagna, Spello
• Drive to Spoleto, Roman ruins, cathedral, Rocca Albornoziana, Ponte del Torri.
• Bevagna walking tour including crafts workshops.
• Spello walking tour including Roman ruins, Piazza Mattoetti, Villa Fidelia.

Overnight in Perugia

Day 9: Orvieto, Rome
• Drive to Orvieto, old town tour including cathedral and Piazza del Capitano del Popolo.

• Drive to Rome.
Overnight in Rome

Day 10: Rome; United States
• Fly home.

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Sample Pricing

Per person from $10,890 for this 10-day sample Tuscany and Umbria itinerary.

For more information, to book, or to speak to an R. Crusoe & Son tour specialist, please call us at 800-585-8555.

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Chianti and Super Tuscans. A Brief History.

Thank Cosimo III de’Medici, the Grand Duke of Tuscany, for Chianti. This Italian red was first produced in the 13th century as a white wine, though little is known about its early incarnation.

     In 1716, Cosimo declared that only four Tuscan villages—Castellina, Gaiole, Radda, and Greve—and a spit of hilly land near Spedaluzzo would henceforth be the sole official producers of Chianti.

     Slowly, Chianti metamorphosed into a red wine, though the grapes used were, one again, unknown. In the 1890s, the Italian statesman Baron Bettino Ricasoli standardized the ideal recipe for “modern” Chianti: 70 percent Sangiovese grapes, 15 percent Canaiolo, 10 percent Malvasia and or Trebbiano, and 5 percent other local red varieties.

     Nearly a century later, the Denominazione de Origine Controllata (DOC), overseen by the Italian government, established the Ricasoli Formula for Chianti, a Sangiovese-based red with a maximum of 30 percent Malvasia and/or Trebbiano added.

     At the same time, however, a group of Chianti vintners banded together and skirted the DOC regulations to create what they believed would be superior Chianti. They called it Super Tuscan, and the name stuck. Some wanted to make Chianti using only Sangiovese grapes; others wanted to introduce French grapes such as Cabernet Sauvignon and Merlot. Still others wanted to age the wine in new oak barrels. A quick look at your local wine shop will tell you that these innovators have been tremendously successful.

     Most Chianti on those same shelves falls into two designations: Chianti DOCG and Classico.  Chianti DOCG (Denominazione de Origine Controllata e Garantita) is made from a blend of grapes grown within seven Chianti sub-zones and grapes grown outside Chianti. The sub-zones are: Colli Fiorentini, near Florence; Chianti Rufina, near the commune of the same name; Classico, in the heart of modern Chianti; Colli Aretini, around Arezzo; Colli Senesi, in the Siena hills; Colline Pisane, around Pisa; Montespertoli, near the commune of the same name; and Montalbano, in Chianti’s northwest reaches.

     Classico grapes are grown strictly within Cosimo’s original four Chianti towns—Castellina, Gaiole, Radda, and Greve. In general, Classico tend to be medium-bodied with plenty of tannins and floral, cherry, and nutty notes. It can be aged in the bottle for up to 20 years.

     Basic Chianti, on the other hand, is known for its fruity notes of cherry, plum, and raspberry and is are best opened three to five years after bottling.

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