Leaving the city of Florence, orange-roofed buildings slowly give way to the rolling, green hills of Tuscany, studded with the famous hill towns. The towns are all different, yet somehow distinctly Tuscan, their walls and fortresses still preserved after so many centuries. In the villages, restaurants serve Chianti drawn from barrels, with big platters of meat, cheese and hunks of bread.
There are many things to do in Tuscany, and this is not a definite list. However, if you dream of driving through vineyards and villages, here are five indulgent ways to spend an afternoon (or five) in the region.
Take the time to visit one or more of the small, medieval towns tucked into the countryside. This is your chance to marvel at the old walls, and walk through twisting laneways lined with crooked windows. Take your pick between tourist towns with sweeping views and multiple souvenir shops, or remote, rural villages where locals are surprised to see unfamiliar faces.
We visited the tiny walled village of Monteriggioni where Gladiator was filmed, still fortified after all these years alone on the hillside. Grey clouds shrouded the village, before dispersing and letting the sunlight catch on the wet stone paths and houses.
The ancient buildings shone in the light and through the gate were dramatic views of rain across the countryside. Inside the walls the few residents worked to sell souvenirs and wine to the visiting tourists.
Regardless of which town you choose to visit, the piazza is always worth your time. Stop for an espresso or glass of wine and watch the locals gossip and chat. If you're lucky enough to visit on market day, stock up on cheese, vegetables and cured meats.
Only 35km from Florence, wine tasting in Chianti makes an easy day trip from the city. Chianti is synonymous with wine and the region is studded with rows of vines and old stone vineyards.
Choose your favourite vineyards in advance or pick them as you go. Stopping by different wineries, and tasting their signature Chianti is a lovely, relaxing way to spend an afternoon. Sipping the dry red is mandatory, and its often accompanied by a sweet or fruity treat. Stopping at a small vineyard, we found ourselves tasting their truffle oil and sticky honeycomb too.
Chianti is readily available throughout Italy, however the best way to try the wine is when you visit the vineyards that make it. If you want a break from wine, take a break to visit one of the small towns in the Chianti region – Radda, Greve and Panzano are popular choices.
Tuscany's second city, Siena, is another jewel of the region. The terracotta city is an enticing maze of steep streets, slanted roofs and sloping skylines, its impressive Duomo dominating the skyline. The huge cathedral was built in the 13th Century. An expansion was planned and construction was started, then abandoned when the plague and Florence conquered the city seven centuries ago.
The Duomo is still well worth visiting, with an extraordinary façade combining elements of French Gothic, Romanesque and Classical architecture and an ornate marble floor. A few blocks away, you can pay your respects to the head and finger of Saint Catherine, the patron saint of Siena, in the Basilica of San Domenico.
After seeing the cathedral and basilica, we wandered through the interlocking alleyways, working our way down to the city centre. The piazza del campo finally came into view, and we sipped wine staring at the empty space and imagining the horses racing around its edges.
The highlight of any trip to Tuscany is choosing a winery restaurant for a long lunch, which somehow embodies the very spirit of Italy. If the weather is good, you'll typically sit outdoors, enjoying panoramic views over the vineyard and distant countryside while you eat.
While some vineyard restaurants lean towards fine dining, my preference is for the more traditional Italian menus, accompanied by the local wine. Even better is if you're invited to a local house for lunch. If farm house lunch invitations aren't forthcoming, find a family-run restaurant at a local agriturismo instead.
Driving through the region, we passed farm houses with stunning views of the valleys and stopped at one for dinner, eating large swirls of pasta with rich tomato sauce and thickly-grated pecorino. We ate outside and the spring air was sweet with hints of the summer warmth as the sun disappeared between the hills.
Probably the most famous landmark in Tuscany (and admittedly my least favourite), you may as well take this opportunity to see the Leaning Tower of Pisa - if only because you're in the area already. Expect crowds and a steady stream of tourists, many only popping by to glance at the tower for a few minutes.
Pisa was the last stop on our Tuscany itinerary. There, we found a walled town with a few restaurants, some shops, and a small amount of industry on its outskirts. We spent the obligatory moments at the leaning tower, staring at the crowds, then wandered through parks and markets to the old town.
We slept in a turret room in a pretty bed and breakfast near the station, but Pisa was still my least favourite place in Italy. Then, in the plane, rising above the clouds, I looked down at the town and saw it from above, its medieval centre and walls as beautiful and perfect as a fairytale kingdom.
Last Updated August 11, 2021