The Ultimate Umbria and Tuscany Self Drive Vacation

8 Day The Ultimate Umbria & Tuscany Self-Drive Vacation from $3,895!

Explore the covetted Tuscan countryside from Perugia to Milan in your own Fiat 500X, coasting the hills of Chianti, visiting medieval cities with histories predating Leonardo Da Vinci. Premium wines will flow free during your winery visits and hand-made pastas will fill your stomach on a self-drive Italian escape of fantastic proportions.

8 day/7 night package featuring Perugia, Buonconvento, Montespertoli, and Casteggio. This program includes accommodation in Deluxe hotels and an Agroturismo stay, daily breakfast, 8-day Fiat 500X rental, local city guides in each visit, private driver/guide in Chianti, wine tastings in Montepulciano, Volpaia and Vignamaggio, Ferrari Museum or Ducati Museum visit and a Modena balsamic wine experience.


  • Meals per itinerary; (B) Breakfast, (L) Lunch, (D) Dinner
  • Rental car
  • Travel funds escrow protection program
  • Entrance fees per itinerary
  • Private guide
  • Select luxury accommodation
  • Emergency assistance


  • Personal expenses
  • Optional tours
  • Customary tips and gratuities
  • Local city taxes
  • Flights
  • Rental car add-ons, i.e. GPS, winter tires, maps, etc.

Daily Itinerary



Rome - Arrival

Upon arrival in Rome, you will meet with your English-speaking assistant who will guide you in picking up your rental car. Once you have your keys in hand, head north in the direction of Umbria, the Green Heart of Italy. Upon arrival in the medieval walled town of Perugia, check-in to your hotel and take the remainder of the evening at your leisure.

Deluxe and Agroturismo Class: Brufani Palace or similar hotels



Perugia and Umbrian Villages

Your morning will be dedicated to exploring the hilltop city of Perugia with its compact historic center and rambling maze of medieval streets. Your local guide will introduce you to the streets of the city as well as the artisans, which inhabit them. Following your tour of Perugia, you may want to consider an optional visit to the Umbrian villages of Torgiano and Deruta, listed among the most beautiful Italian villages. Torgiano, the city of wine and olive oil, produces the only DOCG wine in Umbria and it’s here you have the option to join a cooking class at Tre Vaselle. Deruta is a town of artisans, with a rich deposit of raw clay, everyone in town talks about the art of pottery and ceramics and you can participate in an optional ceramic class while here. (B)

Deluxe and Agroturismo Class: Brufani Palace or similar hotels



Perugia – Valdichiana - Buonconvento

Today you will begin your journey into picturesque Tuscany. Your drive will take you through Valdichiana where you will visit the villages of Cortona, Montepulciano and Montalcino. You may want to consider an optional wine tasting and cellar visit at Avignonesi or horseback riding on Mt. Amiata along the way. Finally, you’ll arrive in Buonconvento, an ancient settlement south of Siena where the Arbia and Ombrone Rivers meet. Check-in to your hotel and spend the remainder of the evening at your leisure. (B)

Deluxe and Agroturismo Class: Villa Armena or similar hotels



Explore Val d’Orcia

Following breakfast this morning, your drive will continue its exploration of the Tuscan countryside with a visit to Val d’Orcia, just south of San Quirico. First, visit the small, hilltop Hamlet of Bagno Vignoni, well known for its hot springs. Later, continue to Castiglione, on the edge of the Monte Amiata forests. Finally, visit the ancient walled village of San Quirico d’Orcia. During your exploration of the Val d’Orcia region, you may want to consider an optional truffle-hunting excursion to see how these elusive fungi are sniffed out. At the end of your day, head back to your hotel in Buonconvento. (B)

Deluxe and Agroturismo Class: Villa Armena or similar hotels



Buonconvento- San Gimignano- Montespertoli

Today’s drive will, itself, be magnificent; enjoy the view of the Chianti hills, covered by vineyards and olive trees and the familiar cypresses. You’ll want to break along your journey to visit the small, walled village of San Gimignano, not far from Florence and famous for its medieval architecture and towers, which offer spectacular views of the surrounding valley. Don’t linger too long, however, as you may miss your wine tasting at a beautiful mansion in the Tuscan countryside. Following your wine tasting, continue your drive to Siena. With its narrow streets, Gothic Duomo and a myriad of Renaissance art, Siena is described as one of the best-preserved medieval cities in Italy. Upon arrival, check-in to your hotel and take the remainder of the evening at your leisure. (B)

Deluxe and Agroturismo Class: Villa Le Calvane or similar hotels



Chianti Wines and Castles

Drive into the heart of Tuscany and into the Chianti-shire, with the breathtaking hilly countryside as your backdrop, until you reach two historic wine estates where some of Tuscany’s best wines are produced, Volpaia and Vignamaggio. You’ll enjoy a wine tasting at each of these villa estates, which have been owned and run by noble families throughout the centuries. First, visit Volpaia, with an actual wine-flowing pipeline running like veins through the village. Take time for your wine tasting and lunch with a spectacular view of the vineyards. After lunch, you’ll visit Vignamaggio, a 15th century villa and winery in the heart of the Chianti Classico region with a fascinating connection to Leonardo Da Vinci and the myth of the Mona Lisa. After your wine tasting here, return to your hotel for the remainder of the evening at your leisure. (B,L)

Deluxe and Agroturismo Class: Villa Le Calvane or similar hotels



Montespertoli – Bologna or Maranello – Casteggio

Your Tuscan journey will continue with a drive to Lombardy, passing along the beautiful Via Emilia, leading to the land of Parmigiano Reggiano and Parma Ham, balsamic vinegar and hand-made pastas. Your first destination will either be Bologna, to visit the Ducati Factory, or in Maranello, to visit the prestigious Ferrari Museum, with a stop in the hills of Modena for lunch and to learn about the production of balsamic vinegar and visit the home of the most famous of Italian cheeses, Parma. Later you’ll arrive at Prime Alture Winery, where you will enjoy a traditional Tuscan dinner and your final night in Tuscany. (B)

Deluxe and Agroturismo Class: Prime Alture or similar hotels



Casteggio – Milan – Return

This morning, after breakfast, you’ll make your way to Milan to Malpanesa Airport to return your rental car and to continue on to your next destination. (B)