You will pick up your car in Rome, either at the airport or the downtown office of the rental company. We will send you your first day's driving directions via email prior to the tour and the rental company will provide you with a road map to get you to Spoleto. Once you arrive, the owner of our hotel in Spoleto will meet with you to provide you with the week's driving directions and maps and to answer any questions you have about the tour. Cristiana has worked with us for years and will function as our in-country representative for this tour.

The Day's Highlight: Driving up the winding streets of medieval Spoleto to your hotel near the top of the town, you will know you are now in the real Italy!

Drive Details: 160 km (2:30 hours) from Rome's airport: the drive today is mostly on freeway getting to Umbria and Spoleto to start the tour.

About The Town: Although Spoleto has some fantastic Roman ruins above town, it is a perfect display of a medieval city with its winding streets and dark alleys. It also has great cafes and nightlife and so is an outstanding place to start the tour.

Special Event of the Day: You will have the option to take a detour on your way to Spoleto to visit the Cascate delle Marmore waterfalls, the largest human-created waterfall in the world. This was designed by the Romans to divert a local river. If you go straight to Spoleto, you'll have time to explore this fantastic, mysterious city of cobblestone streets and stone archways.

The Day's Highlight: Montefalco is one of Umbria's many jewels. The city sits above the Umbria plain with an incredible view over the picturesque landscape of rolling hills and vineyards.

Drive Details: 117 km (3:00 hours): although the distance is shorter today, the drive is mostly on smaller side roads as you make your way from one great Umbrian town to the next. Stopping in each town will make this a full day!

About The Town: Spello is situated on a limestone outcrop above the flat Umbrian plain. A walled town with Roman structures, the main street runs from the lower gate on the plain to the upper gate high above.

Special Event of the Day: Our route takes you past several wineries producing the famous Sagrantino of the Montefalco area. We recommend two estates for you to visit. Purchase a few bottles for your enjoyment in Italy or to take home!

The Day's Highlight: The restored historic center of Assisi, now a UNESCO heritage site, with its Saint Francis Basilica and castle above the town. While Assisi is justifiably popular with travelers, we recommend you take time to wander off the main street and see what Assisi is like for the locals.

Drive Details: 139 km (4:00 hours): this is a loop drive that allows you to avoid packing again, since you will be returning to Spello. The drive features two incredible towns, Assisi and Gubbio, the latter home to the annual colorful Festa Dei Ceri .

Special Event of the Day: Stop two kilometers out of Spello at a traditional Umbrian olive mill. The owner mills olives both for his estate and for other landowners in the area. The olive oil is award-winning and makes a great gift.

The Day's Highlight: The Etruscan town of Perugia has a fantastic center and the city is quite busy as it houses a major university. You can spend several hours here wandering the many streets, eating lunch in a pizzeria, and looking at shops full of potential finds.

Drive Details: 152 km (4:00 hours): The drive starts on the flat Umbrian plain as we head to the ceramics center of Deruta. Crossing over from Umbria into Tuscany, we enter Perugia and take you directly to a parking lot where you can park and walk around this incredible city. There is some freeway driving as we get you into and out of Perugia, while the final stretch from Cortona to Montepulciano is on small country roads.

About The Town: Montepulciano is a medieval walled town built on a ridge, with many beautiful Renaissance style palazzi and churches. The town is very pedestrian-friendly and a great place to walk, so park your car at the hotel and enjoy! Montepulciano is the center of the Vino Nobile wine area.

Special Event of the Day: This day is filled with possibilities! In the Umbrian town of Deruta, we take you to the Grazie ceramics factory, the oldest business in town and family-run for hundreds of years. The ceramics are amazing, you can tour the factory, and the family ships your purchases home for you!

The Day's Highlight: A visit to the St. Antimo abbey is something no one should miss. The grounds are beautiful and the monastery is surrounded by a magical setting. If you are lucky, your arrival time will coincide with the prayers of the resident monks, who pray seven times per day using traditional Gregorian chants.

Drive Details: 68 km (2:00 hours): the undulating landscape of the Val d'Orcia valley passes beneath you on this drive. You are in the heart of Tuscany! Dreamlike Renaissance towns including Pienza and Montalcino are fantastic places to spend a few hours. We have purposefully limited the driving distance today because there are so many great things to do on this route.

About The Town: Montalcino is set on a ridge overlooking the valley below. It is the center of the Brunello wine industry and makes a fantastic overnight stop. Montalcino is small enough so you can wander every street but large enough to have the shops, cafes, and vinoteca (wine bars) you need.

Special Event of the Day: Purchase lunch supplies in one of the towns along the route and then take time to stroll the small dirt roads leading away from the St. Antimo abbey, having a picnic in a setting you will never forget.

The Day's Highlights: The Abbazia di Monte Oliveto Maggiore is one of the most famous abbeys in Tuscany. The main church has 36 frescoes, including famous ones by Signorelli (1497) and Sodoma (1505). A beautiful, spiritual place to visit.

Drive Details: 60 km (1:30 hours): the driving distance is short today since you will want to spend several hours at the Oliveto Maggiore abbey and time in Buonconvento. Plus, you'll want to arrive in Siena early since the city offers so much. Siena is a large town but we route you directly to the hotel, after which you can either return your car and enjoy the city on foot or keep your car for your return to Rome tomorrow.

About The Town: Siena is the best preserved medieval city in Europe, a true masterpiece of art and architecture with its Gothic Duomo, museums, and famous buildings. It is alive with its residents and visitors and a fantastic place to visit.

Special Event of the Day: Celebrate the end of the driving portion of your tour by getting out of your car to visit Siena's shell-shaped square "Il Campo", the scene of the mad horserace "The Palio". Relax, enjoy a great meal, and watch the locals as they stroll on the Corso.

The Day's Highlights: We have arranged an excellent three-kilometer walk of Siena, which takes you to both the famous sights and out-of-the-way residential and student quarters. The walk is optional but it is a great way to get to know the city.

Drive Details: No driving today. After the morning walk, check out of your hotel and continue your Italy travels either by car (if you kept it) or public transportation.

Special Event of the Day: Purchase some last souvenirs, take a few photos, or just watch the locals on your last day in Siena.