Tuscany itinerary: Seven days of hilltown gems

A vacation blueprint for spending one week exploring the great hilltowns of Tuscany & Umbria

Pienza—Montalcino—Volterra—San Gimignano


Seven days of hilltown gems: Day by Day

Day 1 - Cortona

Where to spend the night
Hotels in Cortona (day 1)
Hotels in Gubbio (day 2)
Hotels in Perugia (day 3/4)
Hotels in Assisi (day 4)
Hotels in Montepulciano (day 5)
Hotels in Montalcino (day 6)
Hotels in San Gimignano (day 7)
Make your way to Cortona, whose hilltop perch hides paintings by Signorelli and Fra’ Angelico and whose valley is peppered with Etruscan tombs.

Lunch in the countryside at Il Falconiere.

If you have time before dusk, climb past the vegetable gardens to the shattered fortress at the top of the ancient walls for a view that stretches as far as Lake Trasimeno to the south.

Have a light dinner at La Grotta and spend the night in Cortona.


Day 2 - Gubbio

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.In the morning, take the side road toward Lisciano, where you get on the SS416 over the Umbrian border to Umbertide. Switch here to the SS219 for Gubbio, a stony border town at the edge of a deep, wild range of the Apennine mountains.

If you like views and short hikes, take the cable car up Gubbio’s mountain and then climb the short distance to the top to explore the ruins of an old fortress and the wooded slopes surrounding it.

The best dinners in town are at the Taverna del Lupo, after which you can wander the streets to see the illuminated medieval buildings before turning in for the night. Spend the night in Gubbio.


Day 3 - Perugia

The SS298 leads to Perugia, now a city and the capital of Umbria, but still full of hilltown character.

Take the day to wander its superb painting gallery and visit its churches—including a converted pagan temple that is the oldest church in Umbria.

You can also check out the underground streets of the medieval city, preserved in the 16th century to serve as bastions for a fortress.

Perugia has one of the best passeggiata evening strolls in Italy, a few hours of which do wonders to work off a meal from one of its excellent restaurants before heading to your hotel for the night. Spend the night in Perugia.


Day 4 - Assisi

Head out early for a side trip to Assisi across the valley. After admiring the frescoes by Giotto and other trecento masters in the Basilica di San Francesco, you can either scale the medieval alleys to the well-preserved fortress above or take a countryside hike to St. Francis’ old monastery halfway up the wooded mountain.

Have lunch outside the walls at La Stalla, one of Umbria's best country trattorie.

You can spend the night here in Assisi or cross the valley back to Perugia to spend the night.


Day 5 - Todi, Montepulciano

Drive to Todi to pass the morning in this quintessential Umbrian hilltown from the Middle Ages with its High Renaissance temple just outside the walls.

After lunch at the Umbria restaurant, get on the SS79bis to the SS71 north. After 42km, branch onto the SS146 through Chiusi to Montepulciano.

This is one of the biggest of the hilltowns, full of life and Renaissance palace facades, and with streets so steep that most are cut with steps.

The wheezing climb to the top of town is worth it for the small painting gallery and hulking Duomo.

If you can manage another short climb, the bell tower on the civic palace flanking the cathedral offers a wonderful view on clear days.

After your workout, find somewhere to crash and spend the night in Montepulciano.


Day 6 - Pienza, Montalcino

If you didn’t make it to Sangallo’s perfect Renaissance church outside Montepulciano’s walls—a foil to the one in Todi—see it quickly in the morning.

But leave by 11am so you can make it to nearby Pienza to see its central piazza, the epitome of Renaissance city planning, and find picnic fixings for lunch.

During riposo drive to Montalcino, where you can spend the afternoon enjoying their beefy Brunello red wine inside the ramparts of a medieval castle. Spend the night in Montalcino.


Day 7 - Volterra, San Gimignano

Drive past Siena to Volterra to pass the late morning and early afternoon communing with the Etruscan urns in the archeological museum and peeking in at the early 15th-century frescoes in San Francesco church.

Also take a gander from the panoramic promenade at the Roman ruins below town, but get to San Gimignano by evening to enjoy the Medieval Manhattan emptied of tour bus crowds.

Spend the night in San Gimignano and see as much as you want of the town, its towers, and its heavily frescoed main church the next morning. (OK, so technically this is a seven-and-a-half day trip.)



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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