We think the best time to visit Tuscany is in summer when the vineyards are green and vines drooping with grapes ready to harvest and pastures are full of sunflowers following the sun’s daily path.

Having stayed in the larger cities of Florence and Sienna on past visits we decided to settle in the smaller town of Arezzo for a few days so we could explore the countryside north and south of it.

Make sure you enter the old town before 5pm our host warned us otherwise you won’t be able to drive your car in. And, follow the map we have provided; do not trust the navigation system (very deceptive). We understood why once we entered the gates of the historic old town. The streets are a maze of narrow alleys with colourful flags hanging on street corners.

Giostra flags flying in the streets of Arezzo

Giostra flags flying in the streets of Arezzo

Stephano looks after his family-owned apartment on the first floor of a building built in the 16th century where we are staying. He is excited that our visit to Arezzo coincides with the Giostra Del Saracino (the annual jousting festival) being held at the weekend telling us that there will be plenty of things happening in the lead-up. Check-in is complete and the car is parked in a garage so the streets can be kept clear for the practice sessions.

Stepping outside into the small square there are two police officers guarding the small square outside our apartment. Why are they guarding the spot; are they expecting big crowds or hooliganism? “No, it’s just to keep the streets clear in preparation for the joust. The area is the base for setting up the knights in armour before the joust”, the policewoman who speaks impeccable English tells us. Sonia proudly tells us that she is a competitive flag-waver and has visited Australia for a competition. Both officers are helpful with suggestions about what we should do and see during our few days in the area.

Our first stop is the main square, Piazza Grande. A beautiful square unique for both the coats of arms which adorn the facades of the medieval buildings around the square and for its sloping red brick surface, it is known as home to the annual Giostra and the Fiera Antiquaria, a monthly antique fair where up to 500 dealers fill the square on the first Sunday of every month. Enchanting at the best of times, it is even more so as we watch musicians rehearse in preparation for the Giostra.

Piazza Grande, Arezzo - Giostra de Saracino

Piazza Grande in preparation for the big jousting competition

The Giostra dates back to medieval times and continues the tradition where the town separates into four quarters (each quarter has their own flag) during the Giostra. Two knights are nominated to represent their quarter in the joust. Dressed in medieval costume, the knights, cheered on by their supporters and residents of their quarter, ride into the square to strike the Saracen (a wooden figure covered in armour) with their lance. The team which hurts the figure the most wins.

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We are enlightened about the jousting tradition when we come across a local dressed as a knight standing outside the doorway of the official contest office. He invites us in to show us memorabilia while giving us the history behind the joust tournament in his limited English. An abbreviated description: in the 14th century, the people of Rome called the people of countries on the east side of the Roman Empire (Persians, Turks, Arabs and all Muslims) Saracens. A number of battles were fought between the two religions where the Christians defeated the Muslims. The recreation of these battles by staging festive jousting contests started in the 16th century.

Saturday night arrives and the town is bustling in anticipation. There is a festive spirit as many enjoy an evening out for aperitifs and a meal before the highlight. We do the same! We partake in an evening ritual we have adopted by stopping at the bar where we had enjoyed our coffee earlier in the day to enjoy a refreshing Aperol Spritz with tapas before continuing on around the corner for a beautiful meal in the garden setting at Osteria il Grottino.

Taking a stroll to digest our dinner before having a gelato, we arrive on Corso Italia just as the parade is commencing. Drummers, trumpets, armoured warriors, flag-wavers, jousters on horseback create a wonderful precursor to what is yet to come.

Armoured knights, Arezzo

The parade having passed and with a gelato in hand we continue on to the arena in the Piazza and find a vantage point. Tickets for the event seating has been sold out in advance so we find a spot among the crowd lining the perimeter of the square to listen to the bands and fanfare before the competition starts. Then it starts. Turn by turn the knights on horseback thunder down the narrow alley heading straight to the Saracen accompanied by the roar of the crowd in support of their knight. Hearing both is exhilarating.

No time is wasted on the contest and before we know it, it’s all over and we scurry back to our apartment before the jovial crowd disperses.

Our conclusion

If you are interested in medieval history and would like an authentic experience, the joust season is the perfect time to visit Arezzo. Our honest opinion, we would say any time is a good time. Stay a few days because there is much to see in do in the town and surrounding countryside.

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A little more info

Where we stayed:

Il Mezzanino is in the historic centre. A modern apartment in a historic building, it captures the charm of Arezzo’s past. The apartment is well placed to walk to the main tourist attractions (Piazza Grande, the Cathedral of San Donato and the Santa Maria della Pieve church). Listen out for the church bells chiming and the sound of Gregorian chants emitting from the small church in the courtyard outside the apartment on Sunday mornings.

Some of the other towns we visited in the area:

  • Castiglion Fiorentino is a little walled town sitting on a hill with picturesque views over the surrounding countryside 19km from Arezzo. It sits on the road between Arezzo and Cortona and worth stopping for a look on the way. Sonia, the policewoman we met in Arezzo suggested we visit. It is her home town and she runs a B&B in the town – Suites San Michele which is where we will base ourselves on our next visit to the area.
  • Cortona is hilltop town about 28km from Arezzo with fantastic views to Lake Trasimeno and across the southern Tuscan countryside.  The town was made famous by the author Frances Mayes in her book and subsequently in the film “Under the Tuscan Sun”. Wander its streets and into the beautiful Piazza della Republica where the nativity scene was filmed.
  • Montepulciano is another hilltop town about 60km from Arezzo via Cortona. We detoured taking a scenic drive along the back country roads lined with sunflower farms, vineyards and orchards to reach the town. A historic town full of palaces, churches and pretty squares and steep streets it provides stunning views over the valleys that we had just driven through. The area is known for its Nobile wine and there are plenty of shopfronts for family-owned vineyards in the town where you stop to taste and buy.

And, one more thing:

If you liked this post, you may like our recommendation on taking a drive in the Chianti area of Tuscany.