Tuscany itinerary: 8 Days of Great Art

A vacation blueprint for spending 8 days amid the glories of the Renaissance and Old Master paintings in Tuscany and Umbria


8 Days of Great Art: Day by Day

Day 1-3 - Florence

Where to spend the night
Hotels in Florence (days 1-2)
Hotels in Siena (days 3–4)
Hotels in Sansepolcro (day 5)
Hotels in Perugia (days 5–7)
Hotels in Assisi (day 6)
Hotels in Cortona (day 8)
Spend at least three full days in Florence, the city that invented the Renaissance. The short list of masters whose work fills the city’s museums includes Giotto, Masaccio, Donatello, Leonardo da Vinci, Botticelli, Michelangelo, and Raphael.

These Renaissance Men reveal their artistic secrets in the world famous collections of the Uffizi Galleries, the museums of the Pitti Palace, and the Accademia (Michelangelo's David), and in churches such as Santa Maria Novella, Santa Croce, and Santa Maria delle Carmine.

Try not to strain too many mental muscles, for on the evening of day three you must head south to Siena to spend the night and prepare yourself for a completely different, late-medieval school of painting.

Brace yourself with a medieval meal at the Nuova Grotta del Gallo Nero. Spend the night in Siena.


Day 4 - Siena

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.Spend the morning of day four in Siena with Simone Martini and Ambrogio Lorenzetti’s masterpieces of medieval secular art in the Palazzo Pubblico, and after lunch hit the art-filled Duomo and its museum of Gothic sculptures and a lookout over the burnt-sienna cityscape.

In the evening, dine away your impending art overdose with a meal at La Torre and take a relaxing walk through the lamp-lit streets and see the beautiful Piazza del Campo by moonlight. Spend the night in Siena again.


Day 5 - Siena, Sansepolcro, Monterchi, Perugia

On the morning of day five, get a good overview of the entire Sienese school with a visit to Siena’s Pinacoteca painting gallery.

Grab a sandwich for lunch so you can get on the road to drive to Sansepolcro, stopping along the way to see Piero della Francesca’s Madonna del Parto in Monterchi, one of the only pregnant Madonnas in Italian art by this ethereal early Renaissance master.

Spend the afternoon in Sansepolcro’s Museo Civico with its Piero masterpieces—which rival great works here by Signorelli and others. If you want to spend more time at the museum, stop here for the night and a wonderful homecooked meal at the Fiorentino; otherwise push on in the evening to cross into Umbria and make Perugia by nightfall. Spend the night in Perugia.


Day 6 - Perugia

Spend all day in Perugia, the city that produced Perugino and Pinturicchio. Art lovers can spend hours in the Galleria Nazionale dell’Umbria, the best collection anywhere of Umbrian art. Masterpieces by Perugino and his student Raphael are scattered around town as well.

Perugia’s very good restaurant crop awaits to give you time to relax and prepare yourself for Giotto the next day. Spend the night in Perugia again.


Day 7 - Assisi

Get up early in the morning to make the short trip over to Assisi. The basilica of San Francesco here houses fresco cycles by the earliest Renaissance masters: Sienese like Simone Martini and Pietro Lorenzetti, and Florentine-school founders Cimabue and his star pupil, Giotto. Visiting the church will fill up your morning, but take a break for lunch and wander outside the walls for a countryside feast at La Stalla.

You could spend the afternoon and the night here in Assisi, or after lunch you could cross the valley back to Perugia for the afternoon and take a trip outside the walls to the painting horde in San Pietro church, have one last peek inside the Galleria Nazionale, and spend the night in Perugia again.


Day 8 - Cortona (and maybe Montepulciano, Pienza, Montalcino)

Head back into Tuscany to make your last stop at Cortona, hometown of Renaissance master Luca Signorelli and baroquie Pietro da Cortona.

Fra’ Angelico also spent time here, and the towns modest museums and churches all have small but choice collections of masterpieces.

If all the art has become one big blur and you need to recuperate, you are close to both the hilltowns of southern Tuscany (Montepulciano, Pienza, Montalcino, etc.) and the thermal spas at Chianciano Terme.



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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