Tuscan & Umbrian Countryside featuring Italy's Charming Hill Towns

From $4,449.00 CAD

On a journey through the less-traveled country roads of Umbria and Tuscany, discover another side to the Italy you love. Explore the Umbrian hill town of Spoleto, where the gilded façade of the cathedral rivals with the silvery sheen of the olive trees, and stroll Assisi’s old city. Hunt for truffles in Umbria. In Siena, stand inside one of Tuscany’s most ancient piazzas. Visit Florence, the “Cradle of the Renaissance.” 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.

View Itinerary

MUST-SEE INCLUSIONS

  • Explore historic Siena and see the famous piazza of the Palio Horse Race.
  • Discover Florence, the "Cradle of the Renaissance."
  • Surround yourself in the mystery of the Umbrian hill town of Spoleto.

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.
  • Savor the famous Brunello red wine during a musical tasting at a winery in Montalcino.

CULTURAL EXPERIENCES

  • Behold the unique water-filled piazza in the village of Bagno Vignoni.
  • Enjoy 3 nights in a restored Tuscan villa.
  • Hunt for truffles with a local expert and his truffle-sniffing dogs.

HOTELS

INCLUDED

Stay:
  • 11 Days
  • 10 Nights
Meals:
  • 9 Breakfasts
  • 3 Lunches
  • 5 Dinners
1768050
Terms, conditions and restrictions apply; pricing, availability, and other details subject to change and/ or apply to US or Canadian residents. Please confirm details and booking information with your travel advisor.

Itinerary

  1. Overnight Flight

    On 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.

    Accommodation: Villa Santa Barbara, Montefalco

  2. Rome, Italy

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

    Meal included: Dinner
    Accommodation: Villa Santa Barbara, Montefalco

  3. 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 every fall season.* 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 the Umbrian countryside, as you make yourself at home for the next 3 nights.

    Meal included: Breakfast & Dinner
    Accommodation: Villa Santa Barbara, Montefalco

  4. Umbria - Assisi - 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).

    Meal included: Breakfast, Dinner & Lunch
    Accommodation: Albergo Le Terme, Bagno Vignoni, Orcia Valley

  5. 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.

    Meal included: Breakfast, Dinner & Lunch
    Accommodation: Albergo Le Terme, Bagno Vignoni, Orcia Valley

  6. Umbria - Orcia Valley

    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 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 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.

    Meal included: Breakfast & Lunch
    Accommodation: Villa San Lucchese Hotel, Chianti Countryside

  7. Orcia Valley

    Embark on a culinary journey through the undulating landscape of the Orcia Valley. Begin your day with a visit to an artisanal pasta factory, producing the local specialty – pici – with its organically-grown wheat. Pause in Pienza (UNESCO), a Renaissance village where flowers and plants adorn the cobblestoned streets. 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.

    Meal included: Breakfast
    Accommodation: Villa San Lucchese Hotel, Chianti Countryside

  8. Orcia Valley - 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 where your hotel is located.**

    Meal included: Breakfast
    Accommodation: Villa San Lucchese Hotel, Chianti Countryside

  9. Chianti Region

    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 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.

    Meal included: Breakfast

  10. Chianti Region

    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.

    Meal included: Breakfast & Dinner

  11. Chianti Region - Tour Ends

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

    Meal included: Breakfast

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