FROM $4,399

Tuscan & Umbrian Countryside Tour Featuring Italy’s Charming Hill Towns

Discover the stunning, scenic country roads of Umbria and Tuscany while exploring the captivating cities of Rome, Florence, Siena, Orvieto, Spoleto, and Assisi. Experience the magnificence of country life in a pristine Umbrian hill town and relax in a restored Tuscan villa. Wander medieval streets as you delve into the rich history and culture of Italy. Savor the regional flavours and sip on Chianti and Brunello as you live the Dolce Vita and soak up the sun in Tuscany.

Tuscan & Umbrian Countryside Tour Featuring Italy’s Charming Hill Towns

DEPARTURE DATE: May 22, 2024
Countries Visited: Italy


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 Etruscan hill town of Orvieto, where one of history’s rarest frescoes is on display inside a Gothic cathedral. 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. 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.

Travel Dates & Pricing

May 22, 2024from $4,399 CADPer Person

What's Included

  • 9 night escorted coach tour from Rome to Tuscany
  • 9 night accommodations including 3 nights in a restored Tuscan villa.
  • 9 Breakfasts, 2 Lunches, 4 Dinners
  • 2 Choice on Tour Options
  • Must-See Inclusions: Surround yourself in the mystery of the Etruscan hill town of Orvieto; Discover Florence, the "Cradle of the Renaissance."; Explore historic Siena and see the famous piazza of the Palio Horse Race.
  • Cultural Experiences: Take a hands-on cooking class in a 12th-century abbey; Behold the unique water-filled piazza in the village of Bagno Vignoni.
  • Culinary Inclusions: Experience a home-cooked meal in one of Umbria's country homes; Sample pecorino sheep-milk cheese at a local farm in the Orcia Valley; Savour the famous Brunello red wine during a musical tasting at a winery in Montalcino.
  • Taxes


1Wed May 22Rome, Italy
2Thu May 23Rome - Orvieto - Umbria
3Fri May 24Umbria - Spoletto
4Sat May 25Umbria - Assisi
5Sun May 26Orcia Valley - Pienza
6Mon May 27Pienza - Bagno Vignoni
7Tue May 28Pienza - Siena - Chianti Region
8Wed May 29Chianti Region - Florence - Chianti Region
9Thu May 30San Gimignano
10Fri May 31Chianti Region - Tour Ends

Day 1 – Rome, Italy

Italy’s dynamic capital city beckons. Get a taste of the local culture and start your journey at a delicious welcome dinner.

Day 2 – Rome – Orvieto – Umbria

Olive and cypress trees accent the Etruscan hill town of Orvieto. Stroll the historic streets with a local expert and visit the prominent Gothic cathedral to gaze at a remarkable Signorelli fresco. Continue to discover Orvieto on your own this afternoon. Eat, drink, and disappear into the local scene before taking in the splendors of country life in a pristine Umbrian hill town, your home for the next 3 nights.

Day 3 – Umbria – Spoleto – Olive Oil Mill – Umbria

Medieval palaces command the foreground of ancient Spoleto. In the shadow of the Apennines, embark on a walking tour to see centuries of architectural history, from the Ponte delle Torri aqueduct to the gilded elegance of the Duomo of Santa Maria Assunta. Explore more of Spoleto on your own before learning about olive oil at a family-run frantoio (olive presser). Venture into a local restaurant in the Nera Valley, where you’ll enjoy a cooking class in a former 12th-century abbey. Dig in to your handcrafted meal for dinner.

Day 4 – Umbria – Assisi – Home-Hosted Lunch – Umbria

Travel 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 honoured guest. Share stories and make an Umbrian friend (or two).

Day 5 – Umbria – Pecorino Cheese Farm – Orcia Valley – Pienza

Leave Umbria for the villages of Tuscany, nestled among the rolling hills and cypress trees of the Val d’Orcia region (UNESCO). Taste the flavours of the region at a local pecorino cheese farm. 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.

Day 6 – Pienza – Bagno Vignoni – Brunello di Montalcino Winery – Pienza

Traverse the Tuscan countryside to 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 multi-sensory tasting, pairing wine with music. Back in Pienza for the evening, maybe you’ll explore the countryside along one of the many white roads that cut through the farmland.

Day 7 – Pienza – Siena – Chianti Region

Take 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 Tuscany’s Chianti Region takes you to the restored Tuscan villa* where your hotel is located.

Day 8 – Chianti Region – Florence – Chianti Region

Explore Florence, the “Cradle of the Renaissance,” with a local expert on foot. Wander along the glittering storefronts on the Ponte Vecchio, where gold shops adorn the only Florentine bridge to survive WWII. You’ll also take in the Palazzo Vecchio, the Piazza della Signoria, and Santa Croce. Take some time on your own to explore the city’s seemingly endless treasures, both historic and modern. Return to your Tuscan villa in the evening.

Day 9 – Chianti Region – San Gimignano – Chianti Region

Choose** how to explore Tuscan landscape because it’s your choice! Join a local truffle hunter in search of the elusive mushroom and sample the goods yourself -OR- take to the countryside on an ATV adventure along winding dirt roads, followed with a taste of truffle bruschetta. Spend your afternoon in San Gimignano,** whose beautiful 13th-century medieval towers stand tall over the surrounding vineyards. As the sun begins to set, gather with your fellow travellers for a farewell dinner of Tuscan specialties.

Day 10 – Chianti Region – Tour Ends

Your journey through Tuscany and Umbria comes to a close today in your restored Tuscan villa.

Sounds Like Your Kind of Trip?
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