Row of cypress trees in Tuscany in the late afternoon

Stay at Sant’Antonio Country Resort near Spectacular Montepulciano in Tuscany

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!

Pin of Sant'Antonio Country Resort - Recommended place to stay

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.

View of the Tuscan countryside
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.

View of Tuscan countryside from Sant'Antonio Country Resort near Montepulciano

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.

Tuscan farmhouse accommodation at Sant'Antonio Country Resort near Montepulciano
Our two-bedroom apartment is on the ground floor
Living room at Sant'Antonio Country Resort near Montepulciano
Comfortable living room and dining area
Carol Cram walking in the countryside near Sant'Antonio Country Resort near Montepulciano
On a walk on the grounds of the resort
Shaded walkway at a country resort in Tuscany
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 main piazza in Montelpulciano in Tuscany
Carol in the Grande Piazza in Montepulciano
Looking over the Tuscan countryside from Montepulciano at sunset
Sunset over Tuscany from Montepulciano
Large medieval buidling with porticos against a darkening sky in Montepulciano, Tuscany
Darkness 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.

Carol Cram in the Ristorante La Grotta in Montelpulciano
Getting settled at the Ristorante La Grotta
Beautifully plated dessert at La Grotta Restaurant in Montepulciano
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 on the terrace at Sant'Antonio Country Resort near Montepulciano
Gregg working on one of our two terraces
Swimming pool at Sant'Antonio Country Resort near Montepulciano
Swimming pool (too cold in October!)
Beautiful walkway at Sant'Antonio Country Resort near Montepulciano
Walkway to our suite
Outdoor dining area at Sant'Antonio Country Resort near Montepulciano
An outdoor dining area for guests
Vista of Tuscany countryside
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.



Booking.com

Tours of the Tuscan Countryside

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:

Do you have a favorite place to stay in Tuscany? Let us know in the Comments below.

Favorite Regions in Italy for the Artsy Traveler

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!).

Map of Italy showing major tourist areas including Rome, Tuscany, and Venice

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 at sunset
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 the many small towns and 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.
  • Bolzano: The South Tyrol Museum of Archaeology

For more details about these and other artsy sightseeing in northern Italy, check out Recommended Places to Travel in Northern Italy.

Venice

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
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 Top Ten Modern Art Museums in Europe.
  • Piazza San Marco late at night when the crowds have thinned
  • Accademia Gallery – 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

For more details about these and other sightseeing options and to plan your trip to Venice, read Venice in Three Days for the Artsy Traveler.

Ravenna

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
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
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.

For my hotel recommendations in Ravenna, read Where to Stay in Italy: My Best Picks.

Tuscany and Umbria

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.

Fortress of Montalcino in Tuscany
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!

For plenty of recommendations and suggestions, read Exploring Tuscany, Umbria and La Dolce Vita and Exploring San Gimignano in Tuscany. Also check out Art Masterpieces in Tuscany Who Don’t Want to Miss.

Rome

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
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.

Read my Rome recommendations and a suggested itinerary for a three-day visit in The Best of Rome in Three Days.

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
View of the Bay of Naples, the city of Naples, and Vesuvius in the distance

Read my recommendations and a suggested itinerary for a Week in the Campania.

Conclusion

I have a lot of posts on Italy for you to explore. Here again are some of the ones I’ve already mentioned along with a few more.

San Gimingnano in Tuscany

Best Itineraries for Exploring Tuscany, Umbria and La Dolce Vita

If you love incredible art, gorgeous landscapes, fabulous food, and world-class wines, then consider exploring Tuscany and Umbria. Along the way, you’re sure to experience la dolce vita–the sweet life.

I’ve put together some suggested itineraries for exploring this gorgeous region of Italy. No matter how many times I return, I always find new things to see. And I never get tired to returning to some of my old favorites like Siena and San Gimignano.

Map of Tuscany & Umbria

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 a few days in Florence (see my suggestions below for enjoying this most Renaissance of cities), three nights in Siena, and 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.

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 can get tiring.

After a week (or maybe two!) in Tuscany, spend another week in Umbria if time allows. Perugia or Assisi are good choices.

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 do love Tuscany, it can get overrun with visitors, particularly in Florence.

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.

For accommodation recommendations, see Where to Stay in Italy: My Best Picks.

Florence

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.

The famous Ponte Vecchio in Florence, Italy
Ponte Vecchio in Florence

TIP: Combat the crowds by visiting the hot spots, such as the Uffizi, the Duomo, and the Piazza della Signoria in front of the Palazzo Vecchio, early in the morning or late in the day.

During 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 and the Museo Nazionale di San Marco which houses the frescoes by Fra Angelico.

Here are sightseeing suggestions for Florence. Make sure you purchase tickets ahead of time for the Uffizi and the Accademia.

Siena

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.

TIP: 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.

Piazza del Campo in Siena, Italy at twilight
Piazza del Campo in Siena, Italy at twilight

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.

Wine Tour

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!

Staying in Siena

You’ll find good accommodation options in Siena in the post Where to Stay in Italy: My Best Picks. Here are more sightseeing options in Siena.

San Gimignano

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 that, apart from the souvenir shops, have barely changed in 700 years.

For an in-depth look at San Gimignano and why it deserves top billing in your itinerary, read Exploring San Gimignano in Tuscany.

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.

Volterra

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.

Scenic Volterra in Tuscany
Scenic Volterra in Tuscany

Noteworthy sites include the medieval frescoes in the Palazzo dei Priori, the remains of the Etruscan Acropolis (the Etruscans were big in these parts), the wonderful Guarnacci Etruscan Museum (more Etruscans), and the Roman Theater complex that includes the ruins of 3rd-century baths.

Read more about the Etruscans in the Artsy Sightseeing section of the Italy Destinations page.

Lucca

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 to choose from), and breathe in the medieval atmosphere.

When we visited, a group of young people dressed in medieval garb were presenting a flag-waving demonstration to the accompaniment of some serious medieval drumming. We were entranced.

Medieval flag-waving in Lucca
Medieval flag-waving in Lucca

Pisa

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.

The Leaning Tower of Pisa and the Duomo, Pisa, IOtaly
The Leaning Tower of Pisa and the Duomo

The cathedral is worth visiting, and you must get someone to take the obligatory shot of you holding up the tower. Drop in to Pisa if you’re driving and you have time; otherwise, don’t sweat it. Tuscany has many more treasures to offer.

Other Towns in Tuscany

Tuscany is one of the largest provinces in Italy, with many worthwhile hill towns to visit, including Montalcino, Montepulciano, Monteriggioni, Cortono, and Pienza.

These are all best visited by car. I’ve also traveled in Tuscany by bus, which works fine if you really don’t like driving.

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 hill towns 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. We enjoyed strolling around the central piazza and ducking into the cathedral. Perugia is laid-back and not overly crowded.

View of the scenic Piazza IV Novembre, main square, a masterpiece of medieval architecture in Perugia, Italy
View of the scenic Piazza IV Novembre, main square and masterpiece of medieval architecture in Perugia, Italy

The highlight of our visit to Perugia was discovering the Civic Museum at the Palazzo della Penna. There, we 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

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.

medieval costume in assisi
medieval costume in museum in Assisi
medieval costume in museum in Assisi
medieval costume in museum in Assisi
medieval costume in museum in Assisi
medieval costume in museum in Assisi

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
Basilica of Saint Francis of Assisi

Gubbio

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.

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.

Roman Theatre outside the walls of Gubbio.
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. 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
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

For detailed information about where to stay in Tuscany and Umbria, have a look at my post on Recommended Places to Stay in Italy That Will Make Great Memories. Some of my favorite places that I’ve stayed in Italy, such as the Hotel Pescille in San Gimignano, are located in Tuscany and Umbria.

Enter your destination below to see a map of accommodation options in the region.

 

Tours in Tuscany and Umbria

Here are some Get Your Guide tour options in Tuscany.

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And here are some tour options in Umbria.

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Conclusion

Have you visited Tuscany and Umbria? Share your recommendations in the comments below. And to further excite your about this amazing region, here are some more posts about what to see as an Artsy Traveler in Italy: