Tuscan & Umbrian Countryside featuring Italy's Charming Hill Towns
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.
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.
Highlights
- Rome is the capital of modern Italy and the historical home of one of the great civilizations in history, the Roman Empire. The historical city was founded in 753 BC and has grown to a size of over 3 million inhabitants today. The city is home to major monuments like the Colosseum, Trevi Fountain and many more. The city was built on the seven ancient hills along the Tiber River. Today it is a collection of neighborhoods with vibrant shops, restaurants and museums just waiting to be explored.
- Spoleto dates back to the Roman period when it experienced great wealth as a city on the Via Flaminia. Today visitors can see Roman monuments, like the theatre, intertwined into the fabric of the hill town. The city is dominated by a grand castle perched at the top of the hill and its elegant cathedral, dedicated to the Assumption of the Virgin. The church houses an original letter from Saint Francis of Assisi. The streets of the city pass grand palaces and hidden piazzas just waiting to be explored.
- Join us on a guided walking tour of the town of Assisi, birthplace of St. Francis. Here you'll discover a blend of Roman ruins, winding medieval streets and beautiful churches that make this a must-see destination. Once a pilgrimage site and historical treasure, Assisi offers you the chance to return to another time. With a history that stretches back to 1000 B.C. (predating the Roman Empire), the town rests among the gently rolling hills of Umbria. Marvel at the Basilica of San Francesco, find an out-of-the-way shop, look out at the stunning landscape, or sit and relax at a quiet café.
- Come to know daily life in the Italian countryside when visiting a local family’s home in Umbria. The family invites us into their home to share stories of rural life in Italy. During your visit you are treated to a leisurely lunch with an array of regional specialties and local wine. A homemade meal of fresh locally-grown products awaits. Perhaps you will dine on a delightful fresh bruschetta, followed by a traditional pasta course, then feast on a savory main course of roast pork, and cap off your meal with a delectable tiramisu. This is an experience of building new friendships highlighted by the tastes of Mamma’s kitchen.
- The city of Siena is a charming hill town in central Tuscany with a city center that has masterfully preserved its medieval architecture. The city radiates out over three hills from its central piazza called Il Campo which is home to Siena’s famous Palio - a horse race and medieval festival that occurs twice a year. Siena strikes the perfect balance as a city that welcomes the students studying at their university, locals conducting their business and tourists taking in the many sights.
- Florence is the regional capital of Tuscany and home to countless Renaissance masterpieces. The city developed great wealth during the late Middle Ages and was the birthplace of the Italian Renaissance that produced great artists like Michelangelo, Raphael, Brunelleschi and many others. Today it is a UNESCO World Heritage site filled with numerous museums, stunning architecture and charming piazzas. The city offers something for everyone from culture, to great food and excellent shopping (like their famous gold or leather).
- San Gimignano is a picturesque hill town in the central part of Tuscany. The town developed great wealth in the middle ages and was home to 70 plus medieval towers. Today, only a handful of the towers are still intact, but at least one is open to the public. The hilltop location allows for beautiful panoramic views over the Tuscan Countryside. The town is also home to shops that sell a variety of Tuscan goods from pottery to wine, cheese and wild boar salami.
Hotels
- Kolbe Hotel — Rome
- Hotel Antica Dimora Alla Rocca, Trevi — Umbria
- Hotel Corsignano, Pienza — Tuscany
- Villa San Lucchese Hotel, Chianti Countryside — Tuscany
Details
- Tour Operator
- Collette
- Start City
- Rome
- End City
- Tuscany
- Duration (Days)
- 11
- Activity Level
- Level 3
What's Included
- 15 meals included
- Rome is the capital of modern Italy and the historical home of one of the great civilizations in history, the Roman Empire. The historical city was founded in 753 BC and has grown to a size of over 3 million inhabitants today. The city is home to major monuments like the Colosseum, Trevi Fountain and many more. The city was built on the seven ancient hills along the Tiber River. Today it is a collection of neighborhoods with vibrant shops, restaurants and museums just waiting to be explored.
- Spoleto dates back to the Roman period when it experienced great wealth as a city on the Via Flaminia. Today visitors can see Roman monuments, like the theatre, intertwined into the fabric of the hill town. The city is dominated by a grand castle perched at the top of the hill and its elegant cathedral, dedicated to the Assumption of the Virgin. The church houses an original letter from Saint Francis of Assisi. The streets of the city pass grand palaces and hidden piazzas just waiting to be explored.
- Join us on a guided walking tour of the town of Assisi, birthplace of St. Francis. Here you'll discover a blend of Roman ruins, winding medieval streets and beautiful churches that make this a must-see destination. Once a pilgrimage site and historical treasure, Assisi offers you the chance to return to another time. With a history that stretches back to 1000 B.C. (predating the Roman Empire), the town rests among the gently rolling hills of Umbria. Marvel at the Basilica of San Francesco, find an out-of-the-way shop, look out at the stunning landscape, or sit and relax at a quiet café.
- Come to know daily life in the Italian countryside when visiting a local family’s home in Umbria. The family invites us into their home to share stories of rural life in Italy. During your visit you are treated to a leisurely lunch with an array of regional specialties and local wine. A homemade meal of fresh locally-grown products awaits. Perhaps you will dine on a delightful fresh bruschetta, followed by a traditional pasta course, then feast on a savory main course of roast pork, and cap off your meal with a delectable tiramisu. This is an experience of building new friendships highlighted by the tastes of Mamma’s kitchen.
- The city of Siena is a charming hill town in central Tuscany with a city center that has masterfully preserved its medieval architecture. The city radiates out over three hills from its central piazza called Il Campo which is home to Siena’s famous Palio - a horse race and medieval festival that occurs twice a year. Siena strikes the perfect balance as a city that welcomes the students studying at their university, locals conducting their business and tourists taking in the many sights.
- Florence is the regional capital of Tuscany and home to countless Renaissance masterpieces. The city developed great wealth during the late Middle Ages and was the birthplace of the Italian Renaissance that produced great artists like Michelangelo, Raphael, Brunelleschi and many others. Today it is a UNESCO World Heritage site filled with numerous museums, stunning architecture and charming piazzas. The city offers something for everyone from culture, to great food and excellent shopping (like their famous gold or leather).
- San Gimignano is a picturesque hill town in the central part of Tuscany. The town developed great wealth in the middle ages and was home to 70 plus medieval towers. Today, only a handful of the towers are still intact, but at least one is open to the public. The hilltop location allows for beautiful panoramic views over the Tuscan Countryside. The town is also home to shops that sell a variety of Tuscan goods from pottery to wine, cheese and wild boar salami.
Pricing
| Option | Price | Departure | Return |
|---|---|---|---|
| Double | USD 4,399.00 | 2026-04-25 | |
| Single | USD 5,299.00 | 2026-04-25 | |
| Triple | USD 4,349.00 | 2026-04-25 | |
| Double | USD 4,599.00 | 2026-05-02 | |
| Single | USD 5,499.00 | 2026-05-02 | |
| Triple | USD 4,449.00 | 2026-05-02 | |
| Double | USD 4,599.00 | 2026-05-23 | |
| Single | USD 5,499.00 | 2026-05-23 | |
| Triple | USD 4,449.00 | 2026-05-23 |
Itinerary
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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.
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Day 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.
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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.
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Day 4: Umbria
Pre-sunrise, consider an optional balloon flight over the Umbrian countryside.** Your included program instead, takes you 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).
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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.
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Day 6: Umbria - 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 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.
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Day 7: Pienza
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 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 an afternoon at leisure, maybe you’ll explore the countryside along one of the many white roads that cut through the farmland.
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Day 8: 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.
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Day 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 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.
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Day 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.
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Day 11: Chianti Region - Tour Ends
Your journey through Tuscany and Umbria comes to a close today in your restored Tuscan villa.