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Tuscan & Umbrian Countryside featuring Italy's Charming Hill Towns
11 day tour from Rome to Tuscany
Tour Operator
Collette
Departures
Jun 6, 2026
–
Jun 26, 2027
Prices From
$3,549
Jun 2026 - Jun 2027
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 façade 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.
Tour Itinerary
Day 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.
Day 2
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.
Day 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 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 4
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).
Day 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.
Day 6
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.
Day 7
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.
Day 8
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.
Day 9
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.
Day 10
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.
Day 11
Chianti Region - Tour Ends
Your journey through Tuscany and Umbria comes to a close today.
Itinerary Dates & Prices
Start Date
End Date
Our Price
Guaranteed
Start Date
Jun 06, 2026
End Date
Jun 17, 2026
Our Price
$3,749
Guaranteed
Start Date
Jun 13, 2026
End Date
Jun 24, 2026
Our Price
$3,749
Guaranteed
Start Date
Jul 18, 2026
End Date
Jul 29, 2026
Our Price
$3,749
Guaranteed
Start Date
Sep 12, 2026
End Date
Sep 23, 2026
Our Price
$4,249
Guaranteed
Start Date
Sep 15, 2026
End Date
Sep 26, 2026
Our Price
$4,249
Guaranteed
Start Date
Sep 19, 2026
End Date
Sep 30, 2026
Our Price
$4,249
Guaranteed
Start Date
Sep 26, 2026
End Date
Oct 07, 2026
Our Price
$4,249
Guaranteed
Start Date
Sep 29, 2026
End Date
Oct 10, 2026
Our Price
$4,249
Guaranteed
Start Date
Oct 03, 2026
End Date
Oct 14, 2026
Our Price
$4,249
Guaranteed
Start Date
Oct 10, 2026
End Date
Oct 21, 2026
Our Price
$4,249
Guaranteed
Start Date
Oct 13, 2026
End Date
Oct 24, 2026
Our Price
$4,249
Guaranteed
Start Date
Oct 17, 2026
End Date
Oct 28, 2026
Our Price
$4,249
Guaranteed
Start Date
Oct 24, 2026
End Date
Nov 04, 2026
Our Price
$4,249
Guaranteed
Start Date
Oct 31, 2026
End Date
Nov 11, 2026
Our Price
$3,749
Guaranteed
Start Date
Nov 14, 2026
End Date
Nov 25, 2026
Our Price
$3,649
Guaranteed
Start Date
Dec 01, 2026
End Date
Dec 12, 2026
Our Price
$3,549
Guaranteed
Start Date
Mar 13, 2027
End Date
Mar 24, 2027
Our Price
$3,999
Guaranteed
Start Date
Apr 03, 2027
End Date
Apr 14, 2027
Our Price
$3,999
Guaranteed
Start Date
Apr 10, 2027
End Date
Apr 21, 2027
Our Price
$3,999
Guaranteed
Start Date
Apr 17, 2027
End Date
Apr 28, 2027
Our Price
$3,999
Guaranteed
Start Date
May 01, 2027
End Date
May 12, 2027
Our Price
$4,499
Guaranteed
Start Date
May 04, 2027
End Date
May 15, 2027
Our Price
$4,499
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Start Date
May 08, 2027
End Date
May 19, 2027
Our Price
$4,499
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Start Date
May 15, 2027
End Date
May 26, 2027
Our Price
$4,499
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Start Date
May 22, 2027
End Date
Jun 02, 2027
Our Price
$4,499
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Start Date
May 29, 2027
End Date
Jun 09, 2027
Our Price
$4,499
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Start Date
Jun 01, 2027
End Date
Jun 12, 2027
Our Price
$3,999
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Start Date
Jun 05, 2027
End Date
Jun 16, 2027
Our Price
$3,999
Guaranteed
Start Date
Jun 12, 2027
End Date
Jun 23, 2027
Our Price
$3,999
Guaranteed
Start Date
Jun 19, 2027
End Date
Jun 30, 2027
Our Price
$3,999
Guaranteed
Start Date
Jun 26, 2027
End Date
Jul 07, 2027
Our Price
$3,999
Guaranteed
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