Tuscany & Umbria Cultural Treasures

  • Sample Itinerary
  • Experiences
  • Pricing
  • Featured Hotels
  • Custom Quote

Set off for the iconic countryscapes of Tuscany before discovering the medieval hilltop villages and green heart of Umbria on this celebration of rustic central Italy. From inspired natural settings and works of art tucked away by time, to tranquil towns of stone and the delicious bounty of verdant lands, delight in the abounding beauty and cultural treasures of Tuscany and Umbria.

Sample Itinerary

Day 1

Arrive to either Pisa or Florence Peretola Airport where you will be welcomed by your private chauffeur. Depart for the countryside nestled between San Gimignano and Volterra where you will check-in to your charming four-star hotel housed within a former 18th century villa. Delight in free time to discover your hotel's expansive 750 acre organic farm estate complete with olive groves, and sprawling meadows. This evening you will enjoy a welcome dinner of typical Tuscan recipes featuring estate produced pasta, olive oil, and honey, at your hotel's charming restaurant.

Day 2

Today you will embark on a privately guided exploration of the ancient hilltop village of Volterra to learn about its ancient Etruscan past and splendid architectural treasures, such as the medieval Piazza dei Priori. From Volterra you will next be chauffeured to the fabled wine region of Bolgheri, located in Tuscany's coastal Livorno province. Arrive at a famed producer of Bolgheri superiore wines where you will enjoy a private tour of the estate's vineyards and cantina, followed by a flight of the winery's stellar Super Tuscan vintages. Your wine tasting experience will be crowned with a private tasting lunch of delicacies prepared by the estate chef. In the afternoon you'll return to your hotel by chauffeur for a relaxing free evening.

Day 3

In the morning set off for the western coast of Tuscany to experience one of the region's loveliest natural treasures, the splendid island of Elba. Depart on a scenic ferry ride to Elba, the largest island within the Tuscan Archipelago, and enjoy a full day spent exploring its crystal blue beaches and captivating flora and fauna with the help of your local expert. Along the way dine on freshly caught fish at a quaint seaside eatery before returning to the mainland by ferry boat, where your chauffeur will be waiting to transport you back to your hotel.

Day 4

Check-out from your country retreat and travel to the serene woodlands surrounding Cortona. Embark on a light guided hike along a nature path leading through picturesque forests and cascading waterfalls, before arriving at a 13th century hermitage founded by St. Francis of Assisi. During your visit learn about the property's fascinating history while stopping to admire its lovely gardens. Depart for the center of Cortona for lunch at a quaint trattoria before enjoying free time to peruse the city's boutique shops and scenic civic spaces, at your leisure. From Cortona your chauffeur will transport you through the undulating emerald hills of Umbria while en route to your 17th century monastery turned four-star luxury hotel in the medieval city of Gubbio.

Day 5

Discover the many medieval riches of Gubbio during a privately guided exploration of the city. Along the way admire the city's delightful stone architecture and hilly streets while visiting such sites as the 14th century Palazzo dei Consoli and stunning Piazza Grande. Enjoy free time to continue exploring more of the city at your leisure or return to your hotel for an afternoon of relaxation. In the evening you'll savor a special dinner of seasonal creations prepared using locally sourced Umbrian ingredients, such as mushrooms, olives, grains, and the region’s prized black truffle, at your hotel's gourmet restaurant.

Day 6

Following breakfast and check-out, your chauffeur will transfer you to the medieval city of Perugia where, guided by a local expert, you will experience this fabled hilltop city during a private walking tour. Along the way learn about its Etruscan roots and importance as a center for culture, art, and learning since the Middle Ages, before delighting in a lunch of typical Perugino fare at a quaint osteria. After a lovely day in Perugia you will be transported to the breathtaking hilltop town of Assisi for check-in to your five-star luxury hotel and spa. Enjoy a free evening to relax and take in the serene surroundings at your leisure.

Day 7

Begin the day with a private walking tour of Assisi's historic center. Stroll along charming Via San Francesco before stopping in the Piazza del Comune for a visit to the church of Santa Maria Sopra Minerva, where you'll examine its ancient origins as the Temple of Minerva built by the Romans in the 1st century BC. After a lunch of typical Umbrian dishes paired with regional Montefalco wines, visit the UNESCO honored 13th century Basilica of St. Francis to appreciate its Romanesque and Gothic architecture and illustrious frescoes by Cimabue and Giotto.

Day 8

After breakfast and check-out, depart by chauffeur for the hilltop village of Deruta, known for its production of exquisite, hand-painted ceramics. Arrive for a visit to a revered maiolica ceramic producer and partake in a special pottery making workshop led by a local artist. When class concludes, set off for the ancient village of Spello for a lunch of traditional dishes from the Spoleto province before delighting in an afternoon walking tour to appreciate Spello's perfectly preserved medieval walls built on Roman foundations. From Spello travel to the beautiful town of Norcia, situated within the Monti Sibillini National Park, for check-in to your sumptuous four-star hotel housed within a restored 16th century palazzo.

Day 9

Today be immersed in the local flavors and food products that have made Norcia an epicurean standout, from its prized black truffles to the tradition of the Norcinerie (butchery shops dedicated to the curing of pork). Enjoy a leisurely guided visit of the town before setting off with a local truffle expert to experience the centuries-old tradition of truffle hunting through the surrounding woodlands. In the afternoon embark on a scenic drive through the emerald landscapes of the Monti Sibillini National Park, stopping along the way to sample local gourmet products made with black truffle, at rustic purveyors nestled throughout the park. In the evening savor a sophisticated dinner of local ingredients prepared with contemporary flair at your hotel's elegant gastronomic restaurant.

Day 10

From the verdant mountain landscapes of Norcia your chauffeur will take you on a scenic drive along Umbria's lovely Lake Trasimeno en route back to Tuscany. Arrive at a family-owned farm located outside of Arezzo where you will enjoy a tasting of the estate’s artisan Extra Virgin Olive Oil before dining on a lunch of rustic farm fresh dishes paired with estate produced wines. From the farm you will travel to the medieval center of Arezzo to discover its stunning Piazza Grande and other architectural treasures during a private walking tour. In the afternoon be transported to your splendid 16th century villa turned five-star hotel for check-in. Delight in the perfume of the surrounding lemon and olive trees as you settle-in to your historic accommodation overlooking the Arno river. Savor an elegant dinner featuring lovely views and sophisticated Tuscan cuisine at your hotel's acclaimed restaurant.

Day 11

Delight in a morning spent discovering the storied wine heritage of Tuscany's Chianti Classico. Begin with a visit to one of Chianti's oldest wineries for a tour of the producer's historic cellars followed by an exclusive five-flight tasting of their premium vintages. Your estate visit will culminate with a delicious lunch of classic Tuscan fare inspired by Chianti Classico wine country and prepared with seasonal ingredients. After lunch, travel by chauffeur to the Renaissance jewel that is Florence. Led by a local expert, embark on a special guided exploration of two noble palazzi (palaces) dating back to the Medici era. After a free afternoon discovering the city independently, celebrate your time in Florence with dinner at a charming osteria in the heart of the city.

Day 12

Following check-out, bid farewell to your extraordinary Tuscan countryside retreat and travel by chauffeur to Florence Peretola or Pisa AIrport, in preparation your return flight or the next leg of your adventure.

Experiences We Recommend

  • Guided historical walking tour of Volterra with visits of Etruscan sites
  • Private winery visit & premium Super Tuscan tasting in Bolgheri
  • Private dining experience at acclaimed winery in Bolgheri
  • Guided tour of the island of Elba
  • Scenic hike along historic forest path outside Cortona
  • Privately guided walking tours of medieval towns of Gubbio & Perugia
  • Guided visit of the UNESCO designated city of Assisi
  • Pottery making class at storied maiolica ceramic workshop in Umbria
  • Guided visit of the ancient Roman town of Spello
  • Expert led truffle hunt for prized black truffles of Norcia
  • Private olive oil mill visit with tasting of Tuscan extra virgin olive oil
  • Exclusive winery tour & premium tasting in Chianti Classico wine country
  • Expert led tour of Renaissance palaces in Florence


The minimum trip length for a CountryBred Encounter is 5 Days/4 Nights

Pricing for our Italy Encounters begins at:

  • $850-$1,000/per person, per day* based on double occupancy and a travel party of two
Small group pricing available for travel parties of four or more

*The final price of your custom tour will be determined by your travel party size, departure dates, trip length, amount of meals included, percentage of guided time requested, cities chosen in your itinerary and signature CountryBred excursions selected. This sample itinerary can also be crafted for solo travelers.

Encounters Include

  • Stays at five & four-star boutique luxury hotels
  • Chauffeured transport for touring & transfers
  • Private touring with professional local guides
  • Engaging activities led by cultural experts
  • Signature experiences with insider access
  • Regionally authentic dining
  • Traveler Welcome Package
  • Taxes & base gratuities

Read Client Reviews

  • Gay B.

    Alentejo to Lisbon
    Above and beyond our expectations for an amazing well organized adventure for 26!!
  • Mark W.

    From Castilla to Basque Country
    Our third CountryBred travel experience guided us through the rich cultural history, food, wine & unique culture throughout central/northern Spain. Our selected experiences coupled with the region/city ambassadors throughout our trip were exceptional and made our experience GREAT! (hotels too!)
  • Barbara R.

    Getaway to Tuscany and Northern Italy
    CountryBred thought of every detail for our trip. We didn't have to think about or worry about anything because they had it all covered by professionals every step of the way. From the chauffeurs, to the private boats, to the ambassadors who were extremely knowledgeable and spoke good English, to the amazing hotels, to the selection of restaurants and wines...WOW!

Crafting the Experience

Experiential travel takes time, passion and local ingredients to make something truly special.

Read more


We turn travel inspiration into unforgettable journeys. Begin the trip design process by filling out the form below and a CountryBred specialist will contact you to get your next great adventure underway.


  • CountryBred Encounters begin at $750-$1,000/per person, per day
  • The minimum trip length for a CountryBred Encounter is 5 Days/4 Nights
  • All CountryBred Encounters are land touring experiences only and do not include airfare
  • Groups of four or more are eligible for small group pricing


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