Tuscan & Umbrian Countryside featuring Italy's Charming Hill Towns

Departures & Pricing

Upgrades, transfers, accommodation and more can be quoted on enquiry — call 1300 414 198.

Itinerary

1. 1

   Rome, Italy

   Italy’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.

2. 2

   Rome - Spoleto - Umbria

   Olive 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.

3. 3

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

4. 4

   Umbria

   In 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.

5. 5

   Umbria - Pienza, Southern Tuscany

   Leave 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.

6. 6

   Pienza, Southern Tuscany

   Embark 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.

7. 7

   Pienza - Siena - Chianti Region, Northern Tuscany

   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 the Chianti countryside takes you to the restored Tuscan villa where your hotel is located.

8. 8

   Chianti Region, Northern Tuscany

   Explore 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.

9. 9

   Chianti Region, Northern Tuscany

   Spend 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.

10. 10

    Chianti Region - Tour Ends

    Your journey through Tuscany and Umbria comes to a close today.

Accommodation

Book this tour

Send us an enquiry and a consultant will be in touch, or call 1300 414 198 for personal help choosing a departure.

You might also like

Tour · Insight Vacations · 8 nights

Country Roads of Tuscany & Central Italy

• Luxury air-conditioned coach with extra legroom and onboard washroom
• Personal radio headsets for guided commentary at top sights
• All hotel and restaurant tips included - no hidden costs

Departs 27 September, 2026 + More Dates

From $4,343 pp twin

Discover more

Stay · Collette · 7 nights

Spotlight on Tuscany

• 7-night stay in the renowned spa resort of Montecatini Terme
• Guided tours of Lucca, Florence, and Pisa's Piazza dei Miracoli
• Tuscan cooking class and farm visit to sample local products

Departs 8 July, 2027 + More Dates

From $4,899 pp twin From $5,949 pp solo

Discover more

Stay · Collette · 7 nights

Spotlight on Tuscany

• 7-night stay in the spa resort of Montecatini Terme
• Guided tours of Lucca, San Gimignano, and Florence
• Tuscan cooking class and wine tasting at a local farm

Departs 4 November, 2026 + More Dates

From $4,749 pp twin From $5,699 pp solo

Discover more