Tuscany is famous for her food and wine, her beautiful landscape and historic cities and towns, her culture, and more - but one thing that many might not realise is that this lovely region of Italy is also a hub for unique sporting traditions. So, if you love sport but you also love a curiosity, be sure to pay attention to this lesser-celebrated but fascinating part of Tuscany’s heritage during a stay in one of our incredible villas in Tuscany!
Want to attend one of these curious events for yourself and to enjoy the excitement and thrills of a good game alongside the fun of a more off-beat sport? Well, then check out our guide to some of Tuscany’s most unique and intriguing sporting events...
Calcio Storico Fiorentino, Florence
Among these unique sporting events, Calcio Storico may just be the most well-known and most cinematic. This annual game takes place in Florence during the third week of June and, as the name suggests, is a precursor to the modern sport of football (or soccer). It is, however, a far more violent and brutal game that blends elements of rugby and boxing with football. Previously a game for aristocrats (and even the occasional pope), it is now a major sporting event in the city that pits volunteer players from each of the four quarters of the city against each other. With few rules, things can get quite heated and violent, especially as thousands of spectators egg the game on! Not for everyone, perhaps, but this is certainly a unique and must-see event for sport-lovers and particularly MMA fans who book a vacation rental in Florence for June.
Bravìo delle Botti, Montepulciano
Many will seek out the pretty town of Montepulciano during a stay in Tuscany as it is a famous wine town and a perfect place to sit back, sip some great local vintages, and unwind on your vacation. However, if you’re interested in a bit of excitement along with your wonderful wine, then come visit during August when the town hosts a rather unique race... Another serious testament to endurance and strength, the Bravìo delle Botti sees participants from each of the city’s eight contrade (or districts) compete in a race through the historic streets of Montepulciano while pushing massive 80kg botti (wooden wine barrels). An event that dates all the way back to the 14th century and was originally a regular race on horseback, it is now more unusual and embraces the town’s important wine heritage, creating a rather unique spectacle. Paired with the many people costumed in medieval clothing, the colourful decorations in town, and the various events and celebrations and this makes for a rather good time indeed during a stay at a villa in Montepulciano!
Giostra Del Saracino, Arezzo
For those who want to step back into history, this long-running sporting event is just the thing! A traditional joust that takes place each September, it brings the Crusades back to life and sees eight knights from the four quarters of the city compete on horseback. Each makes runs at a dummy dressed as a Saracen to try and hit it to obtain the most points and win the Golden Lance. As with the previous event, in addition to the sporting event itself, there are also costumes, parades, music, events, food, wine, and markets to be enjoyed, offering a great time overall! So, book your holiday rental in Arezzo for September to step back in time to experience the Crusades through this fascinating sporting event!
Bikeboobs, Orbetello
From the historic to the new, this event is only in its 4th edition in 2026 and offers a chance to be part of the action rather than to simply observe. An event exclusively for those who identify as women, it is a non-competitve bikepacking event that takes participants from the Tuscan Coast and into the rolling green hills of the Val D’Orcia by bike from the 17th to the 20th of September. With three different routes that can be spread over 2, 3, or 4 days, no deeply technical elements, and stunning surroundings, this unique event offers a magical way to experience Tuscany and sisterhood. So, consider signing up to join in on this special cycling event for women while you enjoy a stay in one of our vacation rentals on the Tuscan Coast!
