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


Week long Tuscan Tour: Day by Day

Day 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.


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.


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

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.



Tips & links

Consider a tour

I'm all for planning your own trip‚ and this website is set up to help you do just that—but some people might just as well prefer to leave all the planning, logistics, transportation, lodging, and gathering of information to the professionals and simply sign up with a guided tour.

Nothing wrong with that. Just take my advice and choose a tour that emphasizes small groups over large crowds, local transport over big tour buses, and fun cultural experiences over sightseeing checklists. You'll have a better time, and probably spend less for it. Here are a few of my favorite tour companies who emphasize just that.

1-5 days

1-2 weeks

Useful links
How it all fits into 2 weeks

A tall order for just two weeks? You bet. But there are three tricks to fitting all you can into such a short time here.

  1. Two weeks actually lasts 16 days (figuring you leave on Friday night for your overnight flight, and you don’t return until two Sundays after). » more 

  2. You're going to fly "open-jaws" into Rome and out of Milan.This will save you a full day of traveling back to where you started to pick up the return flight» more 

  3. You are going to take some guided daytours to visit the towns and sights outside the big cities in order to (a) pack as much sightseeing as possible into a limited amount of time, (b) get a professional guide, and (c) provide all transportation so you can spend your time seeing the sights and not waiting on train and bus connections.

Don't forget to pay attention to the "What to do before you leave" section (next) 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 are meant to work.)

What you need to do before you leave home
How to use this itinerary

The basic itinerary above is pretty packed—a lot of early morning wake-ups, a lot of churches and museums—because there's simply so much to see and do in Italy.

By all means, feel free to prune this itinerary down to something a bit slower paced if you don’t want to spend so much time running around (say, leaving out a few hilltowns—Pienza or Orvieto—or perhaps the Cinque Terre, or maybe Pompeii). I've even gone ahead and whipped up a sane version of this itinerary that leaves out Pompeii and the Cinque Terre.

Think of this more as a blueprint to squeezing in the maximum possible. You should, above all, have fun.

Don't overplan

I will freely admit to being as guilty as anyone of this, but: Please try not to overplan your trip to Italy. That's a two-fold plea:

  1. Plan everything, but don't feel compelled to stick to the plan. I think it's a fine idea to work out all the details of what you plan to do—if nor no other reason than it will help you get a handle of what you are able to get done, and start making the hard choices of what you have time for and what you should leave for the next trip to Italy. (Always assume you will retrun!)

    But then do not book absolutely every second in advance (that leaves no room to adjust things as you go to accommodate changing interests, sudden festivals, or unexpected invitations), and please do not attempt to stick to the schedule if it turns out to be overly ambitious and startrs making you miserable.

    Rememeber Clark W. Griswold, the Chevy Chase dad in the Vacation movies, always bound and detemrined to get to WallyWorld come hell or dead aunties? Yeah, don't be that guy. No one in that family was having any fun.
  2. Don't try to pack too much in. A vacation is not meant to be all about checking sights off a list or dashing from place to place to fit in as much as humanly possible. It's about enjoying yourself.

    So do that. Enjoy yourself. Take a hint from the Italian concept of la bel far' niente—the beauty of doing nothing—and take a break from the sightseeing every once in a while.

    Leave some time to stop and sip the cappuccino.

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  • Reliving the ROME of the Caesars at the Colosseum and Roman Forum (Day 2)
  • St Peter's, The Sistine Chapel, & the Vatican Museums in ROME (Day 3)
  • ROME's Pantheon, Trevi Fountain, and the Spanish Steps (Day 1)
  • The ancient ghost city of POMPEII (Day 4)
  • Capri & the AMALFI COAST (Day 4)
  • Boticelli's Birth of Venus at the Uffizi in FLORENCE (Day 6)
  • Climbing Brunelleschi's Dome on the cathedral of FLORENCE (Day 6)
  • Sipping wine in the CHIANTI (Day 7)
  • Climbing the Leaning Tower of PISA (Day 7)
  • Touring that Medieval Manhattan town of towers SAN GIMIGNANO (Day 7)
  • Michelangelo's David at the Accademia in FLORENCE (Day 8)
  • Giotto's frescoes in ASSISI (Day 9)
  • Hiking the Cinque Terre on THE ITALIAN RIVIERA (Day 10)
  • Crusing the Grand Canal of VENICE (Day 11)
  • The glittering cathedral of St. Mark's VENICE (Day 12)
  • Leonardo da Vinci's Last Supper in MILAN (Day 14)
  • A day on LAKE COMO (Day 15)

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