Food, Wine & the Rolling Hills
foodie focus
off the beaten path
wine lovers

Tuscany & Umbria

5 days, 4 nights

from $2,874 per person (based on 2 ppl)

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.
I Want To Learn More!


Venture to Umbria

Day 1
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.

Taste in Tuscany

Day 2
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.

Tour & Cook in Assisi

Day 3
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!

Uncover Umbria

Day 4
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.

Buon Viaggio!

Day 5
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!
I'm Ready to Book! I Want To Learn More!


Each small group excursion is led by a dedicated tour leader who is personable, knowledgeable and passionate about all things Italian. In addition to your tour leader, you'll also get to encounter numerous local experts, from chefs and wine producers to art historians and farmers, all eager to showcase their craft and take you on a insider's journey through Italy.


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!

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).

Classic Hotels

Getting Around:

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.

Pack your luggage and fall in love!

In Italy, beauty is everywhere. From the rolling hills of the Italian heartland to the jutting cliffs of the Mediterranean coastline. We can’t wait to show you our insider’s Italy, and help you unlock your own passion for the bel paese and la vita italiana!
I'm Ready to Book!

Why you'll love it:

I'm Ready to Book! I Want To Learn More!

Trip Details:

Tuscany & Umbria
Available Dates:
  • April 3-7, 2022
  • October 3-7, 2022
Travel Format:
Group. Have a group? Make this trip private
from $2,874 per person (based on 2 ppl)
5 days, 4 nights

What's Included

What's Not Included

I'm Ready to Book! I Want To Learn More!

Traveler Stories for This Trip

Ciao Andiamo allowed us to discover Italy in ways we never imagined possible. We will continue to use them any time we return to Italy.

U.S. Office

295 W 11th St #6D
New York, NY 10014

+1 917 652 6094

from 9am to 6pm EST

Italy Office

Via Giulia, 21
06038 Spello PG, Italy

+39 380 2138313

from 9am to 7pm (UTC +01:00)

Follow Us

Contact Us