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Tuscany & Umbria

Sep 26 - Sep 30, 2022

5 days, 4 nights

Small Group

From €2,695 per person based on 2 people

Venture through the heart of the Italian countryside while enjoying private tastings at hidden wineries, rustic-style feasts and exploring local farms, majestic hill towns, artistic treasures and more.

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Why You'll Love It
  • Receive special access private tours and tastings at local wineries and enoteche
  • Get your apron dirty with a hands-on cooking class in the hills above Assisi
  • Enjoy special culinary experience changing with the season, such as olive oil pressing and tasting, truffle hunting or wine harvesting
  • Tour through Umbria’s Sibillini mountains and national park, with breathtaking countryside views.
Day 1

Venture to Umbria

Meet your fellow travelers and tour leader in Rome, and head north into Umbria. Enjoy lunch featuring typical Umbrian dishes in a charming Umbrian hilltop village. After a winery tour and tasting in Montefalco (home to the Sagrantino grape and some of the best wines of Umbria), arrive at your accommodations to relax, settle in and enjoy dinner on your own.

Day 2

Taste in Tuscany

Explore deep in the heart of Tuscany with a visit to the medieval town of Pienza (known for its sheep farms and pecorino cheese) or Montalcino (home to the Brunello). Enjoy a winery tour, tasting and lunch at a countryside estate, with a fine selection of Tuscan wines and regional delicacies. Then a drive through the panoramic rolling hills before stopping in Cortona (the setting for “Under the Tuscan Sun”), with free time to explore and dine on your own in the historic center.

Day 3

Tour & Cook in Assisi

After enjoying the morning at your leisure, head to the town of Assisi for a guided tour of the magnificent Basilica di San Francesco, with time to explore the village on your own. In the evening, get swept away by the magic of la cucina italiana in a family-run cooking class in an agriturismo deep in the hills of Assisi. You’ll drink wine, prepare dishes with love and get to feast on your creations!

Day 4

Uncover Umbria

Spend the morning relaxing and exploring on your own in Montefalco. In the afternoon, visit the medieval village of Spoleto, famous for its fortress, tower bridge and Duomo set against a backdrop of Umbrian forest. After exploring in the town, head to a nearby winery for an extended tour and tasting paired with Italian antipasti. Close out the day dining like a local at a traditional pizzeria in the walled city of Spello.

Day 5

Buon Viaggio!

After breakfast, visit one last Umbrian hill town – Orvieto, with its striking gothic Duomo and charming cobblestone streets. Walk and explore in the village before returning to Roma where we bid you arrivederci!

Our Guides

We partner with local guides, drivers, chefs and artisans of the highest caliber across all 20 regions of Italy. Every Ciao Andiamo expert is hand-selected by our team and passionate about sharing the best of Italy with our travelers.


I take personal pleasure seeing my guests fall in love with our country, immersing themselves in the local culture and discovering the foods, wines and traditions unique to each region of Italy.


I love my job because it gives me the chance to meet wonderful people from all over the world. I'm a passionate tour guide in love with my region, and I want to share its treasures with my guests!

Getting Around

In Italy, getting around isn’t always easy, which is why we design each trip to flow as seamlessly as possible. From private transfers to expert guidance and assistance with public transportation, we’ll make sure you get from point A to point B without the stress.

Dedicated Private Driver

Throughout your tour, travel seamlessly in the comfort of dedicated car service, as you journey on daily excursions spanning small towns and off-the-beaten path adventures.

Where You'll Stay

Where you call home when you are away from home can make all the difference. That’s why we’ve handpicked accommodations across all our small group tours that blend a mix of Italian hospitality, comfort and local character (you want to feel like you’re in Italy, not Idaho).

What's Included

Four nights stay in listed sample accommodations (or similar) with daily breakfast

Daily food, wine and cultural excursions

Four meals (lunch or dinner) featuring regional specialties and local wines

Two private winery tours and tastings

Wine tasting at a local enoteca

Hands-on, family-run cooking class

One special culinary experience (changing seasonally), such as visit to a chocolate factory or prosciutto di Norcia aging factory, olive oil pressing and tasting, truffle hunting or wine harvesting

Dedicated English-speaking tour leader and ground transportation

Pick-up and drop-off near center of Rome

What's Not Included

Single supplement (€375), airfare, travel insurance, personal expenditures, meals not specified, guide gratuity (optional)

The Ciao Difference

Every Ciao Andiamo Tour Includes

Expert Local Guides

Private Tours

Insider Access

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