Essential Tuscany & Unexpected Umbria.
10 Days.
Begin in Florence, where art and architecture absolutely rule. This was, of course, the nexus of the Renaissance, so it’s no wonder the city is so culturally rich. We urge you to spend a few extra days getting to know this splendid city before we head into the Tuscan countryside.
San Donato is known for its exquisite ceramics, San Gimignano for its 14 towers. Taste the wine as we drive through the gorgeous countryside. 
See olive oil pressed as it has been for generations (if you’re here during the harvest). Your palate awakens to the magnificence of Chianti and especially its Classico region, where the best of the reds are bottled. Take tastings at several of the local estates we adore.
There’s a lesson on the Palio waiting in Siena as well as an off-the-beaten-path, in-depth look inside one of the contrade (neighborhoods).
Timeless Montalcino is known for its deep red Brunello wine. See (and taste) why.
In the 1400s, Pope Pius II built himself a no-holds-barred palace in Pienza. Step inside—it still stands.
Then into Umbria by way of lively Perugia, a university city with a colorful history.
Though founded by the Romans, Spoleto is best known for its lovely medieval streets. Assisi’s basilica is remarkable, as was the life of its patron saint, Francis. The views from Spello are wonderful, especially in Piazza Mattoetti, where 13th-century frescoes and murals enthrall us. Bevagna is a throwback to the Middle Ages. Craftsmen here still fashion paper from rags. Orvieto, in Umbria’s southern reaches, has a delicate light we can’t put our finger on. You just have to see it for yourself.
End in Rome, where we suggest you extend your visit to take in imperial Roman sites, the Vatican museums, and St. Peter’s.
Have a look at our other suggested destinations for two-couple travel: Normandy; Burgundy; Scotland; Russia.
To request a detailed itinerary for this journey (and others), click here.