Two Weeks in Tuscany - A Very Personal Itinerary

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So many people have asked us: “You’ve prepared all those sample itineraries for every area in Italy except Tuscany. Why?” Our answer was: “Do you really need us to tell you to go to the Uffizi?” Now, however, that the principal sights of Tuscany have become so overrun, maybe it is indeed time to propose some more recondite ideas for a quieter visit to Tuscany:

Day 1
Arrive and get settled in your rental property, explore your nearby town or village’s shops, markets, and potential restaurants.

Day 2
Florence – OK, let’s get it over with: Morning: the view from Piazzale Michelangelo, the church of San Miniato al Monte, and the Masaccios at Santa Maria del Carmine. Afternoon: Florence Cathedral, Baptistery, and Campanile, plus, entering about 90 minutes before it closes, the Uffizi.

Day 3
The Chianti countryside – take out your map and drive to Greve early. Go the office of the Chianti wine-producers consortium (or better yet, email them ahead of your trip) and arrange a couple of vineyard visits. Locate those vineyards and arrange a spontaneous driving tour around them. The surprising thing about Chianti is that even in the height of the summer, those roads with scenery so beautiful it will make you weep aren’t at all crowded.

Day 4
A day in Arezzo, one of Tuscany’s loveliest, most civilized, most unvisited cities: see the Piero della Francescas, of course, but also the Piazza Grande, the church of Santa Maria della Pieve (one of our favorites in all Italy), and the other little churches and civic buildings around the city, not to mention the first-class antique shops

Day 5
Volterra and, especially, Massa Marittima whose principal piazza is not to be believed. Also, the direct north-south drive between these two towns for the Valle del Diavolo (Valley of the Devil), and you’ll see why. Disturbing and unforgettable.

Day 6
Pistoia - one of the real undiscovered jewels of Italy, full of charming streets dating from the Middle Ages and an unusual number of beautiful Romanesque churches. Get a detailed guidebook for Pistoia or stop at the tourist office. Be sure to visit the delightful open-air market in medieval Piazza della Sala, plus the Cathedral (with the St. James altar, a masterpiece of silverwork); the Baptistery; the cathedral square as a whole; and the Ospedale del Ceppo, gorgeous and (by us, at least) totally unexpected. Afternoon at the Medici villa of Poggio a Caiano, with a stop at Carmignano to see Pontormo’s Visitation, one of the most beautiful paintings in existence.

Day 7
Rest

Day 8
Pisa - the Cathedral Square and a walk along the Arno in the morning. Lunch in Lucca followed by a walk around the medieval streets of that gorgeous city.

Day 9
Back to Florence - The Museo Bargello, a wonderful museum overlooked by the masses crowding into the Uffizi and Accademia. Then a visit to the open-air market of Sant’Ambrogio, with lunch in the little “diner” in the market itself. Then a walk around the medieval streets of the city, perhaps visiting the Museo Horne, followed by the Accademia, again entering 90 minutes before it closes, for the David and, above all, Michelangelo’s (unfinished?) Slaves.

Day 10
A visit to the Casentino: Poppi, Camaldoli, La Verna, and, especially, Gropina, one of our favorite churches in Italy.

Day 11
Siena - almost forgot it: the Campo and the Cathedral and the Museum of the Cathedral. That will take a morning. The rest of the day, just hang out and enjoy the spectacle.

Day 12
Three unforgettable abbeys with equally unforgettable scenery surrounding: San Galgano, Monte Oliveto Maggiore, and Sant’Antimo, plus atmospheric Bagno Vignoni, immortalized by Tarkovsky.

Day 13
Fiesole, Settignano, and at least one or two of the Medici villas/gardens in the area

Day 14
Four Southern Tuscan hilltown jewels: San Quirico d’Orcia, Montepulciano, Pienza, and Montalcino

Day 15
Depart and regret not having done even half the above

What have we left out? Tons: San Gimignano and Cortona leap to mind, 90 percent of Florence, the cathedral of Prato, the abbey at Badia a Passignano, the Mugello area north of Florence.