Italy always seemed so overwhelming. If you only have two weeks of vacation time, where should you go? So many great cities! Rome, Milan, Venice, Florence… how to choose? In the summer of 2021, an answer came in the form of a question from a friend: “Want to come and hang out with me on a friend’s farm in Tuscany?”

Read more about the practicalities of travelling to Italy from Canada during the pandemic

And so my first international trip in pandemic times was dedicated to two weeks in Tuscany. We drove up, down and around rolling hills and medieval cities, ate caprese salad, saw the best art in the history of Renaissance, soaked in pools and natural hot springs. I fell hard in love with Italy — one of the most visited countries in the world, and also the top search for Canadians looking to travel in 2021.

If you are wondering how to spend two weeks in Tuscany, here’s what I learned.

View of trees from a farmhouse window in Tuscany
When you wake up to this view, there’s no need to rush to go anywhere else

Slowwwwww travel is good

Staying longer in one place meant less potential for interactions with the Covid virus and a lower carbon footprint — both much needed in 2021. But not trying to sightsee every day of our two weeks in Tuscany also meant time to do “nothing” but listen to the sound of horses, dogs, cooing mourning doves, the insistent incessant cicadas and the wind in the cypress trees; eating local cheeses and fresh tomatoes, falling asleep reading in hammocks, learning how to properly pronounce grazie, cooling off from 37 degree heat with as many dips in the pool as we wanted. Tuscany is a perfect place to tear up the to do lists and just…be.

Liisa at the Siena cathedral Tuscany, Italy
The Siena duomo. Only in Italy would this one of the less visited cathedrals

Start small

Like an Italian meal, sequencing is everything in Tuscany. Our trip started in the countryside, where we could adjust to a quiet pace and appreciate small wonders before being blown away by the region’s showstoppers.

Our first medieval Italian town was Pienza, a compact charmer famous for its cheese (pop: 2,000); then onto Montepulciano with its steep car-free streets and sweeping views (pop: 12,000); and then the vibrant tourist city of Siena, where our jaws officially dropped at the majestic cathedral (pop: 53,000).

It was the perfect way to ease into our first trip since the pandemic started. And it prepared us to finish with a bang in Florence, one of the most visited cities in the world. If you prefer to hit the ground running and then recover, reverse this.

Row of cypress tress in Tuscany, Italy
Photo by Achim Ruhnau via Unsplash

Cypress trees are the most beautiful trees

Driving the Val d’Orcia backroads between never-ending rows of tall cypress trees made me feel like an Italian movie star. They are so simple, so glamourous.

Italian cyclists are not human

How else to explain how many I saw grinding up 15% grade hills at high noon in 40-degree weather seemingly without effort. Related: I learned I like ebikes.

Pink sunset near Chianciano in Tuscay
Our first night in Tuscany, we had this view all to ourselves

Ask a local for their favourite lookout

I bookmarked plenty of “best sunset in…” posts before leaving for Tuscany. And you know what? More than famous Ponte Vecchio in Florence, the best sunset we saw was from a hill right behind our homestay. A short walk up hill, nobody else for miles around, Mount Cetona, Chianciano and Montepulciano rising all around us, just as they would have 500 years ago. We got lucky with a clear sky, which glowed pastel pink and blue like all those Tuscan postcards we would later see in the city gift shops. All of Tuscany is the best place to see a sunset.

After about 10pm, everyone just starts making out in public.

We only saw this in the cities. But we saw it in every city. Wherever there’s a hot view, there are hot people making the most of it.

Red tomatoes in Tuscany, Italy
Photo by Tamara Malaniy via Unsplash

Vegetarians have lots of food options

I was warned that Tuscan cuisine is meat heavy. Maybe that’s true. What’s also true that there are so many kinds of vegetarian pastas and pizzas I never went hungry. A fresh arancini rice ball with eggplant from a food stall in Florence is one of the most delicious things I’ve ever eaten, anywhere. It seems that anyone serving food just wants you to eat well and almost all menus have a numbering system with a legend indicating all allergens, handy for vegans too.

If you think that street is too narrow or too steep to drive (or both) you would be surprised.

Tip 1: If you’re renting a car, get the smallest one possible and then try driving the historic city centres. Tip 2: As a tourist there are some streets you probably shouldn’t attempt. Like, the way to the parking lot atop Montepulciano is not via the gravel road beside the cemetery.

Selection of gelato flavours in Italy

Gelato cures everything

Too hot? Gelato. Too tired? Gelato. And no matter the size of your gelato cup, you should mix flavours. If you only want one flavour, they think you are weird. (Confession: after two weeks in Tuscany, I think I returned 30% comprised of gelato.)

Galileo Galilei's fingers on display in Florence.
Galileo Galilei’s fingers on display in Florence

You’ll see dead people

I knew the Italian Catholics were serious about their saints. I didn’t expect to see so many of their dead bodies, or body parts, on display. As someone who seeks out the macabre when I travel, I was pleased to be able to see the mummified head of St. Catherine in the Siena basilica that bears her name, for example. And the Galileo Museum in Florence showcases two of the astronomer’s fingers – one of them pointed at the sky. (More posts coming soon on all the creepy crypts and catacombs we visited!)

Parade before the palio in Siena, Tuscany.
Macho men representing their Goose neighbourhood in Siena, Italy. Photo by Razvan Orendovici via Flickr

The whole country is basically centuries-old neighbourhood fights and organized displays of machismo.

In Siena, we learned about the palio, the world’s longest-running horse race, which pits the city’s 17 neighbourhoods (contrade) amongst each other for honour. Then in Montepulciano, we saw the steep hills where every August men from different hoods race uphill pushing 80kg barrels uphill. Our guide in Florence told us of bareknuckle “historical football” matches in the public square — and how married couples allegedly will split up during the fight season if they are from different quartiers of the city. All of a sudden, I understood The Sopranos.   

Hot springs runneth over

The very best thing I learned from my two weeks in Tuscany is that this region is covered in hot springs. We were based near Chianciarmo, a spa town which may have seen better days but still boasts the wonderfully relaxing Termali Theia.

But you don’t need to splurge on a  fancy spa either. You can find free hot springs all over in Tuscany. We loved the ones in Bagni San Filippo. White calciferous formations, pretty waterfalls, and cascading pools of hot sulphurous water through a forest do attract crowds, but it’s so big everyone can find their own private pool to soak in.   (More posts coming soon on all the hot springs we visited!)

You may want to move here permanently

The hills of Tuscany are dotted with solitary abandoned farmhouses. You will wonder how much they cost. Before bed, you will scroll through Tuscany real estate listings, and websites dedicated to the dream of 1 Euro house auctions. Because it will be hard to imagine going back to a world where tomatoes don’t taste this good and there are no cypress trees. Good luck. And don’t forget to invite me.