Itinerary
Click the links for more info from VisitsItaly.com
Booking this tour: IV Travel

We suggest you arrive in Rome, pick up your car at either Fumicino or Ciampino airport and head straight for Cortona.  But, arrive as you wish and pick-up the trail as you wish.

This is the small Tuscan city that Frances Mayes put on the map with her smash best-seller "Under the Tuscan Sun".  Inhabited since Etruscan times, Cortona was conquered by the Romans, and became an important medieval city.  Take time to explore the centro storico - the historical center - and enjoy the city's utterly unique character.  
 

Your accommodations are just outside the city of Siena where you will have the freedom to go in a number of different directions.  You might spend one of your days visiting the heart of old Siena and stroll through the Campo di Fiori, the large square which is the stage for the rollicking annual medieval horse race called the Palio, or amble through the ancient streets where you can still hear the echos of ancient times - while you shop in some of Tuscany's finest stores.

You've got wheels, so next day you might want to drive south to the famous wine districts of Montepulciano or Montalcino and have a full-on experience of the Tuscan countryside - far off the fast-moving Autostrada.  Or perhaps, drive east to Arezzo, another of Tuscany's vibrant hill-top walled towns.  No matter which way you go...you can't lose!

If you like wine, you've heard of the Chianti wine district, where some of the world's most popular wines are grown.  Greve is the busy, charming little town in the center of the district, so plan to have lunch in Greve.  But spend most of your time getting lost on the country roads that wind their way around the area.  On the top of every hill you will see jaw-dropping vistas over the vineyards, olive orchards and cypress bordered fields that have been under the hand of man for centuries.  Walk, ride a bike, golf, go horseback riding.

We're not taking you into Florence...not yet.  When you leave the Chianti area we want you to head Montecatini Terme and Alta but we insist you make a couple of longish stops to see two of Tuscany's great old cities.  First, make your way across country to San Gimignano, the "city of the towers" and spend the morning strolling it's evocative medieval precincts.  After lunch, drive to the pretty little town of San Miniato, home of the incredibly tasty - and very expensive - white truffle.  Maybe splurge and have a Tuscan dish incorporating a sliver or two of this justifiably famous truffle.

Later in the day - before or after dinner (your choice) - you'll drive into Montecatini Terme, a beautiful spa town featuring gorgeous Liberty Style architecture from the 1800s.  You don't have to just kick-back and relax in one of the city's fabulous spas (although you can!), you can enjoy a trip up the cable car to Montecatini Alta, a medieval fortress town perching on the mountain behind the city that offers stunning views in just about every direction.

• Drop your car at Florence or Pisa.  If you want to extend your visit and the time for use of the car, let us know.

* VisitsItaly.com reserves the right to select hotels within the same class depending on availability at the time of booking.