On a journey through the less-traveled country roads of Umbria and Tuscany, discover another side to the Italy you love. Stroll Assisi's old city, and explore the Umbrian hill town of Spoleto, where the gilded faCade of the cathedral rivals with the silvery sheen of the olive trees. Visit Florence, the "Cradle of the Renaissance." In Siena, stand inside one of Tuscany's most ancient piazzas. Admire the famous towers of San Gimignano and hunt for truffles in the Umbrian countryside. Delight in regional specialties and Italian wine with every dinner. Feel like a local as you discover the marvels of wine, cuisine, culture, and history.

Call 800-747-0368 for more information or to book today! Mention code 19105293

Tour Operator
Collette
Duration
11 Days
DayDestinationDescription
Day 1RomeOn a journey through Italy's roads less traveled, discover its endless treasures from Rome to Umbria to Tuscany, and the marvels of wine, cuisine, culture, and history in between.
Day 2RomeItaly's dynamic capital city beckons. As arrival times will vary, there is no scheduled sightseeing today. Spend the day as you wish, exploring independently. Get a taste of the local culture and start your journey at a delicious welcome dinner.
Day 3RomeOlive and cypress trees accent the Umbrian hill town of Spoleto. Stroll the historic streets with a local expert and see centuries of architectural history, from the ruins of the Rocca Albornoz castle to the gilded elegance of the Duomo of Santa Maria Assunta. Pause at a family-owned frantoio (olive presser), where olives are pressed each November.* After learning about the many varieties of trees and oil-making methods, join a tasting of the EVOO produced at the mill. Then, take in the splendors of country life in a pristine Umbrian hill town, your home for the next 3 nights.
Day 4UmbriaTravel to Assisi, birthplace of St. Francis. Set out on a walking tour of the old city with a local guide, learning about its history as you stroll the medieval streets. Visit the famous Basilica of St. Francis. Later, a local family welcomes you to their country home for lunch as their honored guest. Share stories and make an Umbrian friend (or two).
Day 5UmbriaIn the shadow of the Apennines, experience Umbria's epicurean side. Join a local truffle hunter in search of the elusive fungi in the company of his trained, truffle-sniffing dogs. Sample the goods yourself during a rustic, home-cooked lunch before returning to your hotel in the late afternoon.
Day 6UmbriaLeave Umbria for the villages of Tuscany, nestled among the rolling hills and cypress trees of the Val d'Orcia region (UNESCO). Taste the flavors of the region at a dairy farm producing prized sheep-milk pecorino cheese. Snack on some of the cheesemaker's creations and take in the views of the sparse farmhouses and open fields on your way to Pienza (UNESCO), a Renaissance village where flowers and plants adorn the cobblestoned streets. The evening is yours to eat, drink, and explore the local scene.
Day 7PienzaEmbark on a journey through the undulating landscape of the Orcia Valley. Pause in the unique hamlet of Bagno Vignoni, whose central piazza is filled with thermal water once used to cure pilgrims who stopped here on their way to Rome. Then explore hilltop Montalcino, namesake to one of Italy's great red wines, the Brunello. Tour a winery's estate and cellar before indulging in a tasting of these noble red wines. Back in Pienza for an afternoon at leisure, maybe you'll explore the countryside along one of the many white roads that cut through the farmland.
Day 8PienzaTake a guided walking tour through Siena, delving into the local history as you learn about the world-renowned Palio Horse Race. Enjoy free time to explore more of this hilly town, perhaps visiting its cathedral or the town hall's frescoes. An afternoon drive through the Chianti countryside takes you to the restored Tuscan villa** where your hotel is located.
Day 9TuscanyExplore Florence, the "Cradle of the Renaissance," during an extensive walking tour in the company of a local expert. View the Ponte Vecchio, the only Florentine bridge to survive WWII. Take in the Signoria Square and its imposing Palazzo Vecchio, where, for over 300 years, the Medici Family ruled over the city. Admire the Piazza del Duomo, richly adorned by polychrome marble and gilded bronze doors. Take some time on your own*** to explore the city's seemingly endless treasures, before returning to your Tuscan villa in the evening.
Day 10TuscanySpend your morning in San Gimignano, whose 13th-century medieval towers stand tall over the surrounding vineyards. Nicknamed "the Manhattan of the Middle Ages," San Gimignano's towers soar over the landscape making its distinctive skyline stand out against the rolling hills. Taste authentic Italian gelato from an award-winning ice cream parlor while you wander the cobbled streets and gaze up at the imposing towers during time at leisure in this Tuscan gem. Return to your hotel mid-afternoon. As the sun begins to set, gather with your fellow travelers for a farewell dinner of Tuscan specialties.
Day 11TuscanyYour journey through Tuscany and Umbria comes to a close today.
Dates/Pricing

Click Quote or call 800-747-0368 to get additional information on your chosen travel date. Special offers or competitive pricing may be available!

DateDescriptionPrice FromQuote
June 07, 2026Land Only$4,199.00* (USD)Quote
June 14, 2026Land Only$4,199.00* (USD)Quote
June 28, 2026Land Only$4,199.00* (USD)Quote
July 19, 2026Land Only$4,199.00* (USD)Quote
August 02, 2026Land Only$4,199.00* (USD)Quote
September 13, 2026Land Only$4,599.00* (USD)Quote
September 16, 2026Land Only$4,599.00* (USD)Quote
September 20, 2026Land Only$4,599.00* (USD)Quote
September 23, 2026Land Only$4,599.00* (USD)Quote
October 11, 2026Land Only$4,699.00* (USD)Quote
October 18, 2026Land Only$4,699.00* (USD)Quote
October 25, 2026Land Only$4,699.00* (USD)Quote
November 01, 2026Land Only$4,199.00* (USD)Quote
November 15, 2026Land Only$3,999.00* (USD)Quote
December 02, 2026Land Only$3,899.00* (USD)Quote
March 14, 2027Land Only$3,999.00* (USD)Quote
April 04, 2027Land Only$4,299.00* (USD)Quote
April 11, 2027Land Only$4,299.00* (USD)Quote
April 18, 2027Land Only$4,299.00* (USD)Quote
May 02, 2027Land Only$4,599.00* (USD)Quote
May 05, 2027Land Only$4,599.00* (USD)Quote
May 09, 2027Land Only$4,599.00* (USD)Quote
May 16, 2027Land Only$4,599.00* (USD)Quote
May 23, 2027Land Only$4,599.00* (USD)Quote
May 30, 2027Land Only$4,599.00* (USD)Quote
June 02, 2027Land Only$3,999.00* (USD)Quote
June 06, 2027Land Only$3,999.00* (USD)Quote
June 13, 2027Land Only$3,999.00* (USD)Quote
June 20, 2027Land Only$3,999.00* (USD)Quote
June 27, 2027Land Only$3,999.00* (USD)Quote
Lodging
Kolbe Hotel - Rome, Italy
Hotel Dei Duchi, Spoleto - Umbria,
Hotel Corsignano, Pienza - Tuscany, Italy
Villa San Lucchese Hotel, Chianti Countryside - Tuscany, Italy
Disclaimer
* NOTE: Tour prices are land only rates based on per person, double occupancy. Some dates may feature various changes in hotels, sightseeing and inclusions. Please confirm your specific itinerary at the time of booking. Government taxes and fees are additional. Land rates are guaranteed at time of deposit. Certain taxes and fees are to be paid upon exiting the country in local currencies.
Airfare is additional and is available through Collette Vacations.