Strategically located in the center of Italy between Rome, Venezia and Milano, the Regions of Toscana and Umbria offer so very much!  Toscana has a gentile climate and its wonderful seacoast and islands are its best kept secret.  Umbria feature castles and hilltowns such as Orvieto, Montefalco, Assisi, Perugia and more.  On the Tuscan side, Cortona, Siena, Brolio, Pienza, Montepulciano, San Gimignano and Lucca are just a beginning!  The wines of both regions are legendary and the cuisine is emblematic!  Firenze, of course, is famous for its impressive art and culture! 

All in all you will never go wrong in Toscana and Umbria, and here is our favorite itinerary to properly visit these amazing regions!

Day 1USA Departure
From your hometown it’s an overnight flight to Europe!











Days 4-5     Montefalco -Assisi, Bevagna, Sassovivo & area!
Two days now to explore central Umbria!  The frescoes of Assisi were executed by Giotto, among others, and Bevagna is a major craft center.  Sassovivo is an active monastery where vespers are sung each evening - all-in-all, Umbria will not disappoint!

Day 6    M.falco-Cortona-Castiglione Lago-Montepulciano
Westward now skirting Lago di Trasimeno with a chance to visit Cortona (did you read ‘Under the Tuscan Sun’)?   Castiglione del Lago is worth a stop before heading to the Tuscan Hills for your stay in the Colli Senesi - the area all around Montepulciano.  As elsewhere, a variety of hotels in the area allow you to seek the right fit for your desired atmosphere, taste and budget.  Some of our favorite restaurant suggestions will be made to you as well!

Days 7-8                      Montepulciano
Spend a couple of days exploring the area!  Wineries and olive presses abound and we will share tasting suggestions as well as recomending cooking schools, riding stables, bicycle rentals - whatever your interest is, it can certainly be found in Umbria and Tuscana!

Day 9Montepulciano - Siena - Chianti
North now to Siena for a guided look at the medieval town center including the civic palace, whose tower is a symbol of Italy!  Then you’ll be off to the Chianti countryside for your stay!

Days 10-11                Chianti Country
Explore San Gimignano, Radda, Greve, Gaiole and more!




















Days 13-14                               Firenze
Over the next two days you will have a chance to visit the City of the Medici in depth.  Some of the time will be dedicated to a privately guided visit to the David Statue and more of the city’s wonderful museums, and during your free time you will have ample opportunity to shop and explore on your own!

Day 15                                 Firenze  -  USA
Transfer to the airport of Florence (or sometime Pisa and nearby Bologna work best) for your USA–bound flight.  Same–day arrival.


Please note that each of our suggested itineraries is infinitely customizable! You may wish to extend or shorten any of these visits and of course you could add time in Rome, Venice, the Cinque terre, or almost any part of Italy!  We’re just a quick phone call or email away!



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Favorite Itineraries

La Bella Toscana & Umbria
Day 2                                                   Roma  -  Orvieto
On arrival in Roma, consider a couple of days’ visit, or take possession of a rental right away for the drive north along A-1 to Orvieto (it’s just about 2 hours) for the overnight.  Hotel TBA.  In Orvieto as elsewhere, our hotel recommendations will be made just for you to achieve the perfect blend of location, amenities, atmosphere and budget!

Day 3                                      Orvieto  -  Todi  -  Montefalco
Take the morning to explore the impressive gothic duomo and the Museum of Etruscan history and don’t forget to explore the back alleys and streets of this charming hilltop town.  Lunch  on the main square before heading of to Todi’s hilltop site and Montefalco with impressive views!


Day 12Chianti - Firenze
If you’re feeling ambitious you could include Pisa and the walled town of Lucca, or else why not just a leisurely day around Chianti before reaching Firenze.  Return the rental and reach your hotel TBA in downtown Florence.