Every so often when traveling, serendipity rears its delightful head. The plans you’ve made go awry, but instead of facing disaster, you step into something even more wonderful.
That happened to us while traveling a few kilometers out of the fabled town of Montepulciano in Tuscany.
Read about our day leading up to finding Sant’Antonio Country Resort or cut to the chase and scroll down to my review!
Lead-Up to Montepulciano
In Rome, we woke up to the first rainy day of our time in Italy (we’d been in the country two weeks). The clanging at the building site next door to our apartment was slightly muted, much to our relief.
After nine nights, it was time to leave the Eternal City. We were all packed and waiting at the door for our 10:30 Uber. Horrendous Rome traffic delayed him over half an hour, but when he finally arrived, Roberto was cheerful and helpful.
Thirty minutes later, he dropped us at the garage where we found the same smiling attendant and our car already out of its slot and waiting for us to drive it away. What a wonderful service. Shout-out to Parclick!
Arrival in Montepulciano
We made it out of Rome without even one wrong turn—perhaps a record for us! Soon, we were back on the Autostrade speeding north to Tuscany. Ah, Tuscany! It’s one of my favorite places in Europe which is why I set my first novel, The Towers of Tuscany, there. I’m working on two more novels set in Tuscany; perhaps on this trip I’d find more inspiration to finish them.
The beauty of the Tuscany landscape never gets old
After a smooth two-hour drive, we pulled up in front of our hotel for two nights—a lovely Albergo about five minutes outside Montepulciano. Neither of us had ever visited Montepulciano and so decided that on this trip we’d skip our usual visits to San Gimignano and Siena and see something new. Good call!
No Room at the Inn
Except we had a few more hoops to go through before the full Tuscan experience would wash over us.
The proprietor of the hotel looked puzzled when I give him my name. He searched his list, frowned, shook his head.
No, Signora.
Oh dear. I pulled out my phone and showed him my booking on booking.com and said in a somewhat aggrieved tone, We’ve definitely booked! See – October 13 to 15! A little shiver of doubt ran through me as I said this. Wasn’t today October 13?
He peered at my phone. Ah. That’s next year, Signora.
Oh.
And of course the place was full.
Plan B
We piled back into the car and started driving toward a place he suggested. Within three minutes–Google Maps notwithstanding–we were lost. We’ve found that Google Maps doesn’t always work well in the Italian countryside, or in the cities for that matter.
Gregg pulled over and I consulted my phone to see what booking.com had to offer. Fortunately, several options popped up around Montepulciano. We wanted something outside the town in a country setting. Over the years, we’ve had our share of disasters when we’ve booked places within the medieval walls of an ancient town. If you’ve ever done so, you’ll know what I mean. And if you haven’t, trust me.
If you’re driving, never book a place inside the walls of a medieval city. Ever.
Success
After a few searches, I selected Sant’Antonio Country Resort. It ticked all the boxes–countryside, looked pretty, nice big rooms, mid-range price, and best of all, available. I booked it, paid for it, and entered the address in Google Maps. The suggested route took us around Montepulciano where a band of red showed traffic congestion. Another route that was supposed to be slower but seemingly more direct took us across country in a straight line.
Throwing caution to the wind, I decided to ignore Google Maps and the nice GPS lady and directed Gregg along the other route.
On Our Way Again
Soon, we were bumping along dirt roads cleaving through vine-studded fields punctuated by deep green cypresses. In the distance, a row of pale blue Tuscan mountains floated in a smoky autumnal haze.
It was the Tuscany of our dreams. And fortunately, the road, although unpaved, was not undrivable. So, at a leisurely and extremely scenic pace, we eventually arrived at a massive iron gate—the entrance to the grandly named Sant’Antonio Country Resort.
I wasn’t sure what to expect.
I pressed the intercom and a voice told us to drive in as the gates slowly opened. The owners were incredibly welcoming and friendly. They informed us that never in the history of their working with booking.com had anyone ever booked on the website on the same day they wanted to stay. Apparently, the system is designed to reject such bookings.
But for some unexplainable reason, a glitch in the system let us through. How fortuitous!
Heaven at Sant’Antonio Country Resort: My Review
Sant’Antonio Country Resort is everything we love about Tuscany. Here’s why:
Located out in the country but still within a short drive of an iconic hilltown, in this case, Montepulciano
Plenty of free parking and easy to drive to
Gorgeous self-contained units in a renovated medieval convent
Most units with terraces
A swimming pool and many outdoor areas on the grounds
Plenty of country walks and scenic drives nearby
Stunning vistas of olive trees and cypresses at every turn
Excellent reviews
Friendly and accommodating owners who speak English and genuinely love sharing their little piece of heaven with their guests
And at the Sant’Antonio Country Resort, there is even a friendly fox that likes to steal shoes. We were warned not to leave our shoes outside our door because the fox would take them. What the fox does with the shoes is a mystery, but we agreed not to find out.
Our Accommodation at Sant’Antonio Country Resort
The owners very kindly upgraded us to a two-bedroom apartment complete with very comfortable living room, a big dining room, a large bed in the master bedroom, a second smaller bedroom where we stashed the luggage, and two bathrooms.
Oh, and two terraces.
Here are a few photographs of the place.
Our two-bedroom apartment is on the ground floor
Comfortable living room and dining area
On a walk on the grounds of the resort
Beautiful spots for relaxing all over the property
Memorable Dinners in Montepulciano
After a few hours reveling in our good luck, we left around 5 pm for a drive up to Montepulciano which we discovered is a lovely, calm town, much less frenetic than other Tuscan towns such as San Gimignano.
The deal here is food and wine—lots of wine, particularly the vino nobile of Montepulciano. We stopped at a little bar and I sampled my first glass while Gregg had a cappuccino. With about an hour to kill before our dinner reservation (kindly made by our hosts at Sant’Antonio Country Resort), we climbed the cobbled streets to reach the piazza. It was nearly empty in the early evening. I imagine that during the day, the place is mobbed.
Carol in the Grande Piazza in Montepulciano
Sunset over Tuscany from MontepulcianoDarkness falls over Montepulciano
Dinner at Porta di Bacco was served in an ancient room replete with a column (is it Roman?) and brick arches. The wine and food were predictably excellent. I ordered gnocchi with a duck ragout—hearty and tasty. The food here is different from Rome – more country-style and a nice change from the usual fare offered in Roman trattorias, which can get a bit repetitive.
After a moonlit stroll back to the car, we faced the challenging drive in the dark back to Sant’Antonio Country Resort. A drive that in daylight is quick and easy took on a different tenor at night. We made a few wrong turns but eventually got back on track and were soon pulling into our temporary home.
The next night we dined at Ristorante La Grotta, outside the city walls. Located in a 16th-century building, the restaurant was directly opposite the Church of San Biagio, a noted example of Tuscan Renaissance architecture.
Getting settled at the Ristorante La Grotta
My dessert
Church of San Biagio with Montepulciano perched on the hill above
I highly recommend Ristorante La Grotta for a Tuscan splurge. The service was impeccable and the food excellent. It was the most expensive meal we had in nine weeks, but at 110 Euros for three gourmet courses and excellent wine, it was an amazing bargain!
Enjoying Sant’Antonio Country Resort
While at Sant’Antonio Country Resort, we met some fellow Canadians who shared that they’ve visited before, and love returning. I can’t say I blame them!
We spent our day “off” from traveling by taking walks around the property (it stretches for several hectares), enjoying a drive along small country roads in the area, and generally chilling out. We even saw the fox!
Gregg working on one of our two terraces
Swimming pool (too cold in October!)
Walkway to our suite
An outdoor dining area for guests
Beautiful vista of Tuscan countryside near Sant’Antonio Country Resort
Should You Visit Sant’Antonio Country Resort?
If you’re looking for a Tuscan retreat that is reasonably priced (albeit slightly on the high side, but worth it), set in a glorious landscape, and owned by very helpful and friendly hosts, then I can’t recommend Sant’Antonio Country Resort highly enough.
For other places in and around Montepulciano, click the map below.
Many years ago, I took a wine tour of Tuscany that included a visit to a vineyard near Montepulciano. If you have a day to spare while visiting Tuscany, I highly recommend booking a wine tour. Here are a few suggestions.
Other Posts about Tuscany
Over the past three decades, I’ve visited Tuscany at least a dozen times, and every time I discover new wonders to enjoy and fabulous places to stay. For more suggestions about Tuscany, check out these posts:
My favorite regions in Italy range from Milan and the Dolomites in the north to Naples in the south. Unless you have several months to spare, you can’t really “do” all of Italy in one trip.
You’ll spend far too much time traveling and far too little time enjoying. Pick one or two regions and spent a week or two in each.
As Rick Steves says, “travel like you plan to return.”
Map of Favorite Regions in Italy
The map below shows approximate locations of the main regions in Italy that I recommend you explore. I’ve visited all of them except for Sicily (coming soon!).
I’m going to start in the north and move south because we often drive to Italy, so that’s the direction we enter the country from.
Here are the five regions of Italy I suggest you explore:
Northern Italy: Turin, Lake Como, Milan, Dolomites
Venice and Ravenna
Tuscany and Umbria
Rome
Compania: Naples, Pompeii, Amalfi Coast
In this post, I give a brief overview of these areas and provide links to more in-depth posts.
Northern Italy
You could spend at least a week traveling through the regions of northern Italy.
Milan Cathedral
From east to west, I recommend Turin, Lake Como, Milan, and the Dolomites. Spend at least a week in the north (not counting Venice which deserves at least three days on its own). You won’t run out of things to do!
Highlights of Northern Italy
Here are some of my favorite artsy highlights (a by no means an exhaustive list) in northern Italy:
Turin: The Egyptian Museum – Museo Egizio is first-rate. It houses one of the oldest collections of Ancient Egyptian artifacts in the world. Even if you’re only moderately interested in ancient Egypt, put it on your list.
Milan: The Duomo, Da Vinci’s Last Supper, and La Scala just for starters. There’s lots to see in Milan and it has a very different vibe (calmer in my opinion) than Rome.
Italian Lake District: Spend several days exploring small towns such as Sirmione on Lake Garda, the various lakes; gorgeous views, great food, lots of history.
The Dolomites: Drive as far up as you can and then take a chairlift or gondola even higher. The alpine culture is very different from the rest of Italy.
Don’t stint on the time you allocate to visiting Venice. The city is worth at least three days (preferably longer). You could choose to spend a week in the area–three or four nights in Venice, a night in the Veneto to visit Vicenza and Padua, and then head south to spend two nights in glorious Ravenna (more on Ravenna in a minute).
Rialto bridge in stunning Venice
You don’t need a car in Venice and you can reach the other towns in the area by train.
Highlights of Venice
Peggy Guggenheim Museum – one of my very favorite small modern art museums in Europe (read more in 12 Modern Art Museums in Europe.
Piazza San Marco late at night when the crowds have thinned
AccademiaGallery – great selection of Renaissance and Baroque artists in a lovely, old building
Island of Murano to watch glass-blowing and buy glass souvenirs
Duomo and Doge’s Palace: must-see attractions, but go early or late and get reservations to avoid crowds
Enjoying a Vivaldi concert and getting lost in the dark on the way back to your hotel
Ravenna is a delightful small city south of Venice, most famous for the mosaics in the eight Christian monuments on the UNESCO World Heritage list.
While many of these sites, particularly the most famous mosaics in the Church of San Vitale, attract the tour busses, the rest of Ravenna is wonderfully non-touristy. Relax in the main square and watch the world go by. Ravenna has a subtle charm that made me want to write a novel set there just so I could go and stay for a good long while.
Piazza del Popolo in the evening, Ravenna, Emilia-Romagna, Italy
While we were in Ravenna, we watched a bride and groom emerge from a church and get into a red Ferrari, stopped into an art opening and drank white wine with the two Italian artists who were exhibiting their paintings, and enjoyed one of the best meals we’ve ever had in Italy at Ristorante Alexander. Check out the website and make a reservation! The food was to die for and the prices very reasonable.
TIP: When dining in Italy, make use of review apps and websites to find good restaurants. Every time we’ve taken the time to search out well-rated restaurants and to make reservations, we’ve been amply rewarded by fabulous meals.
Highlights of Ravenna: Touring the UNESCO World Heritage Sites
The mosaics in the early Christian monuments are the big draw in Ravenna, as noted earlier.
TIP: Buy your combination ticket for the six UNESCO sites in central Ravenna at any of these locations: the Basilica San Vitale, Mausoleum of Galla Placidia, Basilica of Sant’Apollinare Nuovo, Neonian Baptistery, and the Archbishop’s Chapel.
The sixth site–the Arian Baptistery–is free and worth a visit to view the well-preserved domed mosaic, dating from the early 6th century AD, that shows Christ being baptized by John the Baptist.
At just €9.50 for entrance to all these sites, the Ravenna Mosaics combo ticket has to be one of Europe’s best artsy bargains. In addition to the six sites in central Ravenna, don’t miss the remaining two UNESCO sites. The mausoleum of Theodoric is a short walk from the town center, and the Church of Sant’Apollinare in Classe is an 8-kilometer drive towards the Adriatic coast.
Mosaic in Ravenna featuring the Empress Theodora
Staying in Ravenna
We were driving when we visited Ravenna, and so, as usual, we stayed in a hotel on the outskirts. We then took taxis into the city and from there walked to seven of the eight UNESCO sites in the center of Ravenna. On our last morning in Ravenna, we drove to the Basilica of Sant’Apollinare in Classe.
Toscana! The very name evokes warmth and good living and beauty while at the same time associated with a deliciously turbulent history.
All those towers and walls and fortifications in towns such as San Gimignano and Siena and Lucca were not built back in the Middle Ages because life was easy. The architecture of Tuscan hill towns screams strife.
The Fortress of Montalcino, a hill town in Tuscany
At the same time, the museums and churches of Tuscany burst at the seams with art–much of it created between 1300 and 1600, from the Middle Ages to the Renaissance.
We’ve been visiting Tuscany for years and plan to return. We’ve only recently “discovered” Umbria and were taken with its less touristy, more authentic atmosphere. While I love Tuscany, it can get overrun with visitors, particularly in Florence.
TIP: I recommend allocating at least a week to exploring Tuscany and another week for Umbria. Spend a few days in Florence to see the highlights and then if you have a car, find a house or an agriturismo property to rent for several days or a week in or near one of the medieval towns in Tuscany. Take day trips to other towns, bearing in mind that driving in Tuscany can be slow going on the twisty, narrow roads.
In a typical week, reserve a few days for just staying put and enjoying bella Toscana.
If you don’t have a car, you can still stay in the country, but choose a place that provides some assistance with transportation. You can join local tours such as wine tours (highly recommended!). Some properties offer cooking classes and painting classes.
After your week in Tuscany, spend a week in Umbria. The areas around Perugia or Assisi are good choices.
You won’t run out of things to see. I guarantee it!
The Eternal City takes hold of your psyche with the weight of its 2,000-plus-year history and the central role it has played in the development of western culture.
Rome will not be denied.
Piazza Navona in Rome in the morning
I’ve visited Rome several times since my first trip there with my parents in 1974. During our most recent trip, Gregg and I spent ten days enjoying the city during Gregg’s exhibition of his paintings at a gallery near the Vatican. We lived like locals in an apartment in the same area and set aside time every day to explore new areas of Rome.
Here are additional suggestions for what to see in Rome, including tours.
Naples and the Compania
Naples is kind of crazy–or at least it was when I visited a few years ago. We keep meaning to get down there again to see how or if it’s changed. I rather hoped it hasn’t.
I have a vivid memory of being driven in a taxi through downtown Naples and noticing how the driver barely slowed down at stop signs caked with dirt. Apparently, obeying them was optional. The driver pulled up in front of the National Archeological Museum in Naples, reputed to be one of the best museums in Italy for Roman antiquities. He then turned around and announced chiuso. Closed.
Oh. Those were the days before the Internet took the guesswork out of travel planning. Our only day in Naples was also the only day of the week when the museum was always closed.
That mistake wouldn’t happen nowadays which is a good thing although sometimes I miss the serendipity of the “olden” days when plans could so easily be derailed.
View of the Bay of Naples, the city of Naples, and Vesuvius in the distance
Planning to visit Tuscany and Umbria in the heart of Italy? Excellent idea! If you love incredible art, gorgeous landscapes, fabulous food, and world-class wines, then consider dedicating at least a week (preferably two) to exploring these two iconic regions of Italy.
Tuscany will dazzle you with cities such as Florence, Siena (my favorite) and lovely little San Gimignano. These destinations are all world-class, and for good reason.
Umbria, Italy’s “green heart” offers a slower pace, fewer crowds, quieter towns, and some awesome art. Combine a visit to both Tucany and Umbria to see the best of all possible worlds.
I’ve designed this itinerary to help you take a breath and slow down. Savor museum visits, balance famous sites with lesser-known gems, enjoy local specialties and most of all, relax and let the history seep into your bones.
Explore Italy’s artistic heartland by pairing the Renaissance brilliance of Tuscany with the spiritual calm and medieval charm of Umbria. This itinerary blends world-class museums, hill towns, and vineyard landscapes with quieter, more intimate experiences that are perfect for travelers who want depth without rushing. From Florence’s masterpieces to Siena’s medieval back streets, Orvieto’s dazzling Duomo, and Assisi’s incredible frescoes, you’ll enjoy a beautifully paced journey through two regions that are rich in history, art, and timeless Italian beauty..
The map of Tuscany and Umbria includes all the destinations mentioned in this post. Click a number to read more about the location.
Trip map created with Wanderlog, the best trip planner app on iOS and Android
Suggested Itineraries for Exploring Tuscany & Umbria
Explore both Tuscany and Umbria by car or home-base in one or more of the towns and take day tours to others.
For Tuscany, one strategy is to spend three nights in Florence (see my suggestions below for enjoying this most Renaissance of cities), three nights in Siena, and one or two nights in San Gimignano. During those five days in the Tuscan countryside, be sure to take a wine tour.
For Umbria, divide your time between the three main towns: Orvieto, Perugia, and Assisi, and reserve time for enjoying the rugged countryside.
If you want to explore Tuscany and Umbria by car, pick up your rental car at the Florence airport. Avoid picking your car up at the train station or some other area in central Florence. You don’t need the headache of navigating your way out of the city. Also, if you drive into a ZTL (Traffic Limited Zone) in Florence, you will get ticketed and fined.
After picking up your car at the Florence airport, you’ll be out on the highway within minutes.
TIP: Bear in mind that driving in Tuscany and Umbria can be slow going. If you home-base in a specific area or town, reserve a few days for just staying put and enjoying la dolce vita. Spending every day driving the twisting, narrow roads gets tiring.
After a week (or maybe two!) in Tuscany, spend another week in Umbria if time allows. Perugia or Assisi are good choices.
Here are my recommendations for top towns to visit in Tuscany and Umbria.
Tuscany
If you have only a week to see Tuscany, I suggest you make time for Florence and two of the other towns, such as Siena (my favorite) and San Gimignano, with perhaps a day trip to one other town, such as Montalcino or Volterra.
You kinda have to visit Florence (#1 on the map) because it’s, well, Florence. A sizable percentage of Italy’s finest art is found in Florence, and you owe it to yourself to see it.
Unfortunately, half of the known universe descends on Florence every day (or at least that’s how it feels). I remember wondering if the medieval Ponte Vecchio was strong enough to bear the throngs streaming across it.
Ponte Vecchio in Florence
To beat the crowd in the middle of the day, opt for lesser known but still amazing sites, such as the Masaccio frescoes in the Brancacci Chapel across the river from central Florence, the medieval Palazzo Davanzatti, and the Museo Nazionale di San Marco which houses the frescoes by Fra Angelico.
Florence Highlights
• Uffizi Gallery – Botticelli’s Birth of Venus and an unmatched collection of Renaissance masterworks.
• Accademia – Home to Michelangelo’s monumental David.
• Duomo & Dome Climb – Brunelleschi’s soaring dome with unforgettable city views.
• Ponte Vecchio – Florence’s medieval goldsmiths’ bridge glowing at sunset.
• Piazza della Signoria – An open-air gallery of sculptures in the city’s civic heart.
• Palazzo Davanzati – A beautifully preserved medieval townhouse offering an intimate glimpse into medieval Florentine life.
• Brancacci Chapel – Masaccio’s groundbreaking frescoes that transformed Renaissance painting.
• Museo Nazionale di San Marco – Ethereal frescoes by Fra Angelico in a serene monastic setting.
Staying in Florence
My favorite place to stay in Florence is Serristori Palace Residence. Although a bit on the pricey side, the residence is excellent value because of the size of the one-bedroom apartment, with high ceilings, a panoramic view of the river, and its excellent location about a ten minute walk from the action.
Tours in Florence
Here are sightseeing suggestions for Florence. Make sure you purchase tickets ahead of time for the Uffizi and the Accademia.
Spend at least two nights, preferably more, in Siena (#2). Siena is my favorite city in Tuscany, with enough great artsy sightseeing to keep you as busy as you want to be. You’ll also have time to just hang out in Siena. Walk the narrow cobbled streets, relax in the Campo, and eat a great meal or two complemented by good Tuscan wine.
When you arrive in Siena, head first to the Campo. If the weather is dry, plop down on the 700-year-old bricks and soak up the history.
Siena Highlights
• Siena Cathedral (Duomo) – A Gothic masterpiece with striped marble, intricate pulpits, and a stunning floor.
• Piccolomini Library – Brilliant Renaissance frescoes by Pinturicchio celebrating the life of Pope Pius II.
• Palazzo Pubblico – Siena’s medieval town hall overlooking the Campo, home to landmark civic frescoes.
• Lorenzetti’s “Good and Bad Government” Frescoes – One of the most important political fresco cycles of the Middle Ages.
• Piazza del Campo – The fan-shaped heart of Siena and one of Italy’s most beautiful public squares.
• Torre del Mangia – A slender 14th-century tower offering sweeping views across Siena and the Tuscan hills.
• Santa Maria della Scala – A former hospital turned museum complex with frescoes, archaeological finds, and sacred art.
The Campo can get very crowded during the day. Arrive later in the afternoon, enjoy a glass of wine at one of the cafés bordering the piazza, and watch the crowds disperse as the sun turns the Torre Mangia golden. Your glass of wine will be overpriced, but who cares? You have a ringside seat to one of Europe’s most beautiful public piazzas.
Allocate one of your days in Tuscany to taking a wine tour of the region. Choose a tour that includes Montalcino, home of the scrumptious (and potent) Brunello di Montalcino. The tour I took included a marvelous three-course lunch and visits to three wineries that also included tastings.
Let your guide do the driving! Here’s a good option from GetYourGuide:
Yes, it’s crowded during the day with tour busses, but once they leave, you’ll have beautiful San Gimignano (#3), medieval city of towers, all to yourself. Enjoy top-class restaurants and stroll flood-lit streets. Little has changed, apart from the souvenir shops, in 700 years.
San Gimignano Highlights
• Collegiata (Duomo) – Vivid medieval fresco cycles depicting Old and New Testament scenes in a beautifully preserved Romanesque setting.
• Chapel of Santa Fina – Ghirlandaio’s luminous frescoes honoring San Gimignano’s beloved saint.
• Sant’Agostino – Benozzo Gozzoli’s elegant frescoes illustrating the Life of St. Augustine.
• Historic Towers – Fourteen surviving medieval towers that shape the town’s dramatic skyline.
• Piazza della Cisterna – A picturesque triangular square framed by stone palaces and towers.
• Palazzo del Popolo & Civic Museum – Medieval art, local history, and access to the Torre Grossa for sweeping views.
• Torre Grossa – The tallest tower in town, offering panoramic vistas across Tuscan vineyards and rolling hills.
• San Gimignano 1300 – A detailed ceramic reconstruction of the town as it appeared in the year 1300, offering a fascinating window into its medieval past.
And if you’re looking for something to read while staying in San Gimignano, consider downloading The Towers of Tuscany, my award-winning novel about a female artist in San Gimignano and Siena in the 1300s.
Staying in San Gimignano
Stay overnight in San Gimignano so you can enjoy this magical city without the crowds. Good options are the Hotel Pescille and the Cappuccina Country Resort, both outside the city so you’ll need a car.
Tours to San Gimignano
If you don’t have a car and/or time to stay overnight in San Gimignano, consider taking a day tour from Florence or Siena. Here are some options, some of which include other towns in the area.
Fans of the Medici series on Netflix will recognize the town hall in Volterra (#4) as the stand-in for Florence’s Palazzo Vecchio.
Volterra–known as the City of Alabaster–is considerably less crowded than its neighbor, San Gimignano, and has just as much (maybe more) to offer the artsy traveler.
Volterra Highlights
• Roman Theater – A beautifully preserved 1st-century BCE theater revealing Volterra’s ancient Roman roots.
• Guarnacci Etruscan Museum – One of Italy’s oldest museums, with extraordinary Etruscan urns, bronzes, and funerary sculptures.
• Palazzo dei Priori – Tuscany’s oldest town hall, with medieval frescoes and a tower offering views over the rooftops.
• Volterra Cathedral & Baptistery – A serene Romanesque interior with Renaissance additions and a striking octagonal baptistery.
• Etruscan Gate (Porta all’Arco) – A monumental 4th-century BCE gateway still bearing its original stone heads.
• Alabaster Workshops – Traditional craft studios where artisans carve Volterra’s famous translucent alabaster.
• Medici Fortress – A dramatic hilltop stronghold dominating the skyline (viewable from outside only).
Scenic Volterra in Tuscany
If you’re interested in the Etruscans, then Volterra is a must-see.
Staying in Volterra
Settle into a country place near Volterra and take a break from sightseeing. Agriturismo properties such as Agriturismo Pampilla are perfect places to while away a hot summer after in Tuscany.
Tours in Volterra
You can find tours that take you around some local wineries or teach you Tuscany cooking techniques. How about truffle hunting? That sounds very cool!
The walled city of Lucca (#5) is a charming place to spend half a day. Walk along the top of the walls, visit Lucca Cathedral (Lucca is known as the city of a hundred churches so there’s more than enough to choose from), and breathe in the medieval atmosphere.
Lucca Highlights
• Renaissance Walls – Wide, tree-lined ramparts encircling the city—perfect for walking or biking with panoramic views.
• Duomo di San Martino – A graceful Romanesque cathedral with the exquisite Tomb of Ilaria del Carretto by Jacopo della Quercia.
• San Michele in Foro – A dazzling marble façade rising above the site of Lucca’s ancient Roman forum.
• Guinigi Tower – A medieval tower crowned with oak trees and sweeping views over Lucca’s red rooftops.
• Piazza dell’Anfiteatro – An oval piazza built atop the remains of the Roman amphitheater, now ringed with cafés and shops.
• Torre delle Ore – The city’s tallest tower, offering a classic climb and historic clock mechanism.
• Puccini Sites – Birthplace of composer Giacomo Puccini, with a dedicated museum celebrating his life and work.
On one of my visits to Lucca, I saw a group of young people dressed in medieval garb presenting a flag-waving demonstration to the accompaniment of some serious medieval drumming. I was entranced.
Medieval flag-waving in Lucca
Staying in Lucca
Lucca is a magical place to stay overnight. The virtually traffic-free streets empty out of tourists and you can stroll around the ramparts for a floodlit view. I stayed at Hotel Alla Corte degli Angeli which was inside the town walls. It was delightful!
Tours in Lucca
Here’s an interesting tour option for opera lovers visiting Lucca during the Puccini Festival:
I’ve visited Pisa (#6) once, and that’s enough for me, although perhaps I’m being unfair. The area around the famous Leaning Tower teems with tacky souvenir stalls. I like a good tacky souvenir as much as the next gal, but even I reached my limit in Pisa.
That said, there are some interesting artsy sites to enjoy in Pisa. Your best bet is to go in the late afternoon and stay overnight. That way, you may be able to enjoy the tower and the cathedral without crowds.
Pisa Highlights
• Leaning Tower of Pisa – The world-famous tilting campanile, offering a memorable climb with views across the Piazza dei Miracoli.
• Pisa Cathedral (Duomo) – A stunning Romanesque basilica with striped marble, glittering mosaics, and an elegant nave.
• Baptistery – The largest in Italy, known for its perfect acoustics and remarkable blend of Romanesque and Gothic styles.
• Camposanto Monumentale – A serene cemetery cloistered around medieval frescoes and ancient sarcophagi.
• Museo dell’Opera del Duomo – Sculptures, treasures, and architectural fragments from the cathedral complex.
• Piazza dei Miracoli – The “Square of Miracles,” a UNESCO masterpiece where all the major monuments unite in dazzling harmony.
• Arno Riverside Walks – Charming riverside promenades lined with pastel façades and university energy.
The Leaning Tower of Pisa and the Duomo
The cathedral is definitely worth visiting, and you must get someone to take the obligatory shot of you holding up the tower.
Staying in Pisa
For a place with a view of the leaning tower, check out the Grand Hotel Duomo.
Tours in Pisa
Here’s a guided tour of the bapistery, cathedral, and leaning tower that would be a good bet if you didn’t get tickets in advance:
Tuscany is one of the largest provinces in Italy, with many worthwhile hill towns to visit, including Montalcino, Montepulciano, Monteriggioni, Cortono, and Pienza.
All these small towns in Tuscany are best visited by car. Driving in Tuscany is relatively easy but not speedy. The roads are narrow and twisting. Slow down, relax, and enjoy the journey. Oh – and make way for locals who don’t ‘do’ slow.
TIP: Never (and I mean never!) attempt to drive into a Tuscan hill town. First, you risk getting a stiff fine (being a tourist is no excuse), second, you risk ripping one or both of your side mirrors off your rental car, and third, you risk never again speaking to your partner.
Find the parking lot outside the city walls and walk into the town. Yes, you’ll likely be walking uphill (that’s why they are called hill towns), but some towns such as San Gimignano thoughtfully provide an elevator to take you from the car park to the town.
Others don’t, but if you’re going to travel in Tuscany, you need to be up for some good, stiff walking.
Umbria
Umbria (#7) has much to offer the artsy traveler. The landscape is just as stunning as the landscape in Tuscany, with even more rugged mountains, and the hill towns are as interesting and historic.
Highlights include Perugia, Assisi, Gubbio, and Orvieto.
Perugia
Perugia (#8) is the capital of Umbria and one of its largest towns. Enjoy strolling around the central piazza and ducking into the cathedral. Perugia is laid-back and not overly crowded.
Perugia Highlights
• National Gallery of Umbria – A superb collection of Umbrian painting, including masterpieces by Perugino, Pinturicchio, and early Renaissance masters.
• Piazza IV Novembre – The city’s grand central square, anchored by the elegant Fontana Maggiore and the cathedral façade.
• Fontana Maggiore – A 13th-century marble fountain adorned with scenes of daily life, zodiac signs, and biblical stories.
• Palazzo dei Priori – A monumental Gothic palace housing important civic halls and the National Gallery.
• Perugia Cathedral (San Lorenzo) – A striking interior with notable artworks, including the Baroque sacristy and relics of local saints.
• Rocca Paolina – An incredible underground fortress and “hidden city” of vaulted corridors built by the papacy.
• Corso Vannucci – The lively main street lined with shops, cafés, and a perfect atmosphere for an evening stroll.
View of the scenic Piazza IV Novembre, main square and masterpiece of medieval architecture in Perugia, Italy
The highlight of my visit to Perugia was discovering the Civic Museum at the Palazzo della Penna. There, I viewed the work of Gerardo Dottori, the leader of the Umbrian Futurists and one of the founders of Aeropainting.
The Palazzo della Penna is one of Perugia’s little-known museums that’s worth seeking out. It’s constructed on the ruins of a Roman amphitheater and an ancient Roman road.
One of the highlights of artsy traveling is looking for these lesser-known but amazing small museums (of which Italy has many). They are almost always deserted, and most contain marvelous collections.
Assisi
Assisi really is delightful. It does get crowded because of the famous Giotto frescoes, but not as crowded as places like Florence. Deifnitely stop in and even stay the nght if you can. The frescoes are worth the journey, and then the town itself is a great place to wander.
Assisi Highlights
• Basilica of St. Francis – A two-level masterpiece filled with fresco cycles by Cimabue, Giotto, Simone Martini, and Pietro Lorenzetti.
• Giotto’s Life of St. Francis – Revolutionary narrative frescoes that mark a turning point in Western art.
• Basilica of Santa Chiara – A serene Gothic church housing the relics of St. Clare and early Franciscan artworks.
• Piazza del Comune – The ancient Roman forum turned central square, framed by medieval palaces and the Temple of Minerva.
• Temple of Minerva – A remarkably preserved Roman temple with a striking Corinthian façade.
• Eremo delle Carceri – A peaceful hermitage in the Monte Subasio woods where St. Francis retreated to pray.
• Rocca Maggiore – A dramatic hilltop fortress offering sweeping panoramas over Assisi and the Umbrian valley.
One of the hippest things I saw during our visit to Assisi (#9) wasn’t even on the tourist radar. I spied a small sign in a side street advertising a special exhibition of medieval costumes. As an historical novelist with a yen for all things medieval and Italian, I’d found my bliss.
Here’s a few of the costumes included in the exhibition.
When traveling to small towns in Tuscany and Umbria, check at the tourist office for local exhibitions and events and keep an eye out for posters. You never know what gems you’ll find.
Also taking place while we were in Assisi was an annual festival where all the locals dressed in medieval garb and paraded through the streets. Many other events were included in the festival, but we had neglected to get tickets.
More reason to do your research before you go!
The big draw to Assisi is, of course, the Basilica of Saint Francis of Assisi, with its marvelous frescoes by Giotto. Start your visit to Assisi here, then walk up into the medieval town, and from there continue up to the fortezza for some stunning views.
Basilica of Saint Francis of Assisi
Where to Stay in Assisi
The highly-rated Hotel Umbra is right in the centre of Assisi.
Tours in Assisi
Here’s a guided tour of the Basilica of Saint Francis of Assisi that would be useful in helping you interpret Giotto’s famous frescoes:
What a delightful town! Nicknamed the City of Fools, Gubbio (#10) is unpretentious and relaxed. We spent a pleasant day wandering its cobbled streets, enjoying lunch in the panoramic Piazza Grande, and visiting the municipal museum.
Gubbio Highlights
• Palazzo dei Consoli – A striking medieval palace dominating the skyline, with a museum showcasing Gubbio’s ancient Iguvine Tablets.
• Piazza Grande – A dramatic terrace-like square suspended above the city with sweeping views of rooftops and hills.
• Roman Theater – One of Italy’s best-preserved ancient theaters, set just outside the medieval walls.
• Gubbio Cathedral – A serene Gothic interior with a graceful rose window and notable Renaissance paintings.
• Basilica of Sant’Ubaldo – Reached by funicular, home to the patron saint’s relics and magnificent views over the Umbrian valley.
• Funivia Colle Eletto – A charming open-air cable car offering a scenic ride up to Monte Ingino.
• Historic Ceramics & Craft Shops – Traditional artisans producing Gubbio’s famous maiolica and ceramics.
One of the fun attractions of Gubbio is the Big Barrel, otherwise known as La Botte dei Canonici. The barrel is reputed to be the world’s largest and oldest. It’s worth a photo op, and there’s a gift shop. Entrance is free, so if you pass it during your wanderings around Gubbio, pop in and find out more.
We also checked out the Roman Theatre outside the walls of Gubbio near where we parked.
The Roman Theatre outside the walls of Gubbio
Remember–always park outside the city walls!
Orvieto
The stunning cathedral is the draw to Orvieto (#11), a beautiful Umbrian town perched atop a volcanic plug and worth an overnight stay.
Orvieto Highlights
• Orvieto Cathedral (Duomo) – A dazzling Gothic façade of mosaics and sculpture, with a luminous interior rich in medieval and Renaissance art.
• Signorelli’s Last Judgment Frescoes – A dramatic, visionary cycle in the San Brizio Chapel that influenced Michelangelo.
• Pozzo di San Patrizio (St. Patrick’s Well) – A remarkable double-helix well designed for mules to descend and ascend without crossing paths.
• Orvieto Underground – A network of ancient tunnels, caves, and Etruscan passageways carved beneath the city.
• Torre del Moro – A medieval clock tower offering panoramic views of Orvieto and the surrounding countryside.
• Etruscan Museum (Museo Archeologico Nazionale) – Outstanding artifacts, urns, and bronzes revealing Orvieto’s ancient past.
• Piazza della Repubblica & Historic Streets – Atmospheric lanes lined with stone buildings, cafés, and artisan shops.
Unlike its better known Tuscan counterparts, Orvieto is relaxed and approachable. Park in the large lot at the bottom of the hill and take the elevator or escalator to the medieval upper town.
The facade of the cathedral is unusual in its inclusion of golden mosaics, sculpture, and stained glass.
The stunning facade of the Cathedral at Orvieto
For more information about what to see in Orvieto, check out this article by Rick Steves, my fave travel writer.
Where to Stay in Orvieto
Orvieto makes a good home base for touring Umbria. Borgo La Chiaracia Resort & Spa is a bit of a posh option outside the town that includes a spa. Treat yourself!
Tours in Orvieto
Here are some options including a tour from Rome that takes you to Orvieto and Assisi, a good option if your time is limited.
I’ve traveled a lot in Tuscany and Umbria. Here are the questions I get asked most often:
How many days do you need for Tuscany and Umbria?
A week to ten days is ideal for exploring both regions without rushing. This gives you time two spend at least two nights each in Florence and Siena in Tuscany, and then to explore Orvieto, Assisi, and Perugia in Umbria. With fewer days, focus on just one region; with more time, you add towns such as San Gimignano, Volterra, Montalcino, and Montelpulciano.
Is Umbria less crowded than Tuscany?
Yes. Tuscany attracts far more international visitors, especially Florence, which can be painfully overcrowded. Umbria feels quieter and more authentic, with smaller crowds even in major towns such as Assisi and Orvieto. Umbria is an optimal choice if you’re looking to savor Italy’s medieval charm without tour groups.
Do you need a car for this itinerary?
If you want to explore the countryside, stay in rural hotels, and visit smaller towns than yes, a car is recommended. Rent one from the airport in Florence after you’ve toured the city (don’t drive into Florence!). If you prefer public transit, you can reach Siena and Orvieto by train from Florence, and other towns by bus, although schedules can be limited. Another option is to home base in Siena or Florence and take small group or private tours around the region.
What’s the best home base in Tuscany?
Florence is best for art lovers and museum visits, while Siena works well if you prefer a quieter, more medieval atmosphere and easier access to the countryside. For wine and hill towns, consider basing in the Val d’Orcia near Pienza or Montepulciano, or stay near San Gimignano and visit Volterra and Cortona.
What’s the best home base in Umbria?
Orvieto and Assisi both make excellent bases. Orvieto offers dramatic views, a spectacular cathedral, and good train connections. Assisi has a peaceful atmosphere and some of Italy’s most important fresco cycles. Perugia works well if you prefer a lively university city with excellent museums.
Can you visit both Tuscany and Umbria by train?
Partially. Major cities such as Florence, Siena (via bus), Arezzo, Orvieto, Perugia, and Assisi are connected by train. However, public transportation rarely reaches the hill towns, vineyards, or smaller villages. If you don’t want to drive, choose your bases carefully and rely on guided day tours for harder-to-reach places.
What’s the difference between Tuscany and Umbria?
Tuscany is known for its Renaissance art, wine towns, and famous cities like Florence and Siena. Umbria is quieter, greener, and more spiritual, with medieval hill towns, important fresco cycles such as those by Giotto in Assisi, and far fewer crowds. Visiting both gives you a rich contrast between Italy’s artistic heart and its peaceful countryside soul.
Conclusion
Have you visited Tuscany and Umbria? Share your recommendations in the comments below.
Here are some more posts to give you a taste of Italy or check Visiting Italy to see the full list of posts about Italy.
