Tuscany itinerary: The week-long Tuscan Classic

A vacation blueprint for spending a week visiting the classic art cities and hilltowns of Tuscany

FlorenceLuccaPisaSan Gimignano—MonteriggIoni—Siena—Asciano—
Monte Oliveto Maggiore—PienzaMontepulciano

Days 1-2 - Florence

Where to spend the night
Hotels in Florence (day 1)
Hotels in Lucca (days 2-3)
Hotels in San Gimignano (day 4)
Hotels in Siena (days 5–6)
Hotels in Montepulciano (day 7)
Spend two full days in Florence, seeing as much as you possibly can.

On the evening of the second day drive to Lucca to spend the night.

Day 3 - Lucca

Don't forget to pay attention to the "Before you Leave Home " box at the end of the itinerary covering all the details you need to take care of before leaving home—and be sure to read the "Foolish Assumptions" page about how these itineraries work along with more time-planning tips.Use the next day to explore civilized Lucca’s Romanesque churches, climb its tree-topped tower for a panoramic view, and promenade in the shady park atop the city’s massive 16th-century walls.

Dine at La Buca di San Antonio and stay the night in Lucca again.

Day 4 - Pisa, San Gimignano

Get up early to drop down to Pisa for a morning at the Campo dei Miracoli sights.

Have a quick picnic lunch on the lawn in front of the Leaning Tower, then make your way south to San Gimignano.

Pass the afternoon in the medieval Town of Towers admiring the late-medieval and early-Renaissance frescoes in the Duomo and San Agostino.

Have dinner at Osteria delle Catene and wander the medieval streets after dusk when the tour buses have left and the city is your own. Stay the night in San Gimignano.

Day 5 - San Gimignano, Siena

In the morning, climb San Gimignano's Torre Grossa for a bird’s-eye view of the surrounding countryside and then descend to visit its small museum with its early Renaissance paintings and racy medieval frescoes.

Leave San Gimignano to drive toward Siena, stopping at the tiny hamlet of Monteriggioni still nestled within its medieval walls.

Get to Siena in the early or mid-afternoon and spend the rest of the day with the art treasures of the Duomo and its museum. Spend the night in Siena.

Day 6 - Siena

Spend all day in Siena. In the morning see the artistic masterpieces of the Sienese school in the Palazzo Pubblico, and pass the afternoon visiting the other Sienese sights most daytrippers miss, like the Gothic palaces, Santa Maria dei Servi, St. Catherine’s house, and the city’s public washhouse fountains from the 1200s.

Treat yourself to sinner at the refined Osteria Le Loggie for dinner before turning in. Spend the night in Siena again.

Day 7 - Asciano, Monte Oliveto Maggiore, Pienza, Montepulciano

Before you leave home:
 Book plane tickets
 Book hotels
 Check train times
 Book entry tickets:
    Florence: Uffizi, Accademia (David)
 Learn more about Italy
 Practice your Italian

Get up extra early to drive down the SS438 through Asciano to the side road leading to the Monte Oliveto Maggiore abbey and its remarkable Signorelli and Sodoma frescoes.

Leave plenty of time to navigate the back roads to Pienza for lunch. After your meal, see some of Pienza, with its central square straight out of a Renaissance “ideal city” painting, then hightail it to nearby hilltown of Montepulciano for the late afternoon. Spend the night in Montepulciano.

You can see what you missed of Montepulciano—its travertine palaces, High Renaissance church, and wine cellars converted from the Etruscan tunnels burrowed under the town—the next morning before hopping over to the nearby A1 autostrada that will zip you north back to Florence or south to Rome.

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This article was written by Reid Bramblett and was last updated in August 2010. All information was accurate at the time.

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Copyright © 2008–2013 by Reid Bramblett. Author: Reid Bramblett