If someone would ask what we love about Tuscany, our immediate response is, “What’s not to love?” It’s true! We daresay that many of the quintessential Italian landscapes are in Tuscany. It is one of the most beautiful regions to visit, from its historic towns and villages to the places immortalised by the Giro d’Italia and the famous Strada Bianchi one-day cycling classic race held in the region.
Below is a list of the locations we love to visit and ride in Tuscany. Plus we have an added special treat, we asked our good friend, Australian professional Cyclist and Olympian Grace Brown, to share a few of her favourite rides in Tuscany.
Now, if you’re a huge road racing cycling fan, you may already know who Grace Brown is. She began her professional cycling career in 2015. A few years later, Grace emerged victorious in the Australian National Time Trial Championship in 2019 (ed) and again in January 2022. Grace has quickly risen to the top of Women’s professional cycling in Europe and was recently named Australian’s Women’s Cycling Rider of the Year in late 2021.
Grace rides for a new team in 2022, joining the French Women’s World Tour team FDJ Nouvelle-Aquitaine Futuroscope. She never fails to impress us with her tenacious adaptive approach to professional cycling. It’s been a joy to play a small part in her continued success as a professional cyclist as her cycling skills and technical coach.
Tuscany at a Glance
It’s difficult to summarise everything Tuscany can offer in just a few sentences. But to make it short, this region has it all. You will quickly fall in Love with Tuscany – we know we have – because of its delicious food, beautiful landscapes, unique architecture, and culture. To say that it has an interesting history is an understatement. Tuscany is where the Italian Renaissance was born. Unsurprisingly, it’s filled with dozens of museums housing some of the world’s artful treasures.
Tuscany is made of gently rolling hills, lush vineyards, and seemingly endless beautiful castles. These sights are among the reasons why we love cycling in the region. Plus, the hamlets, churches, and houses that dot the narrow country roads are the perfect scenery as we get to the hilltop towns.
Our Top Places to Visit in Tuscany
Ready to be enthralled by Tuscany? Don’t miss these locations to see the best landscapes and exquisite natural and manmade gifts that the region has to offer:
- Vinci: There is no better place to get to know world-famous genius Leonardo da Vinci than his birthplace. The small lovely village of Vinci is located between Empoli and Pistoia in northern Tuscany. Due to its size, it can go unnoticed. But it’s where da Vinci was born in 1452 and stayed until 1469 before leaving for Florence. Whilst here, take the time to drop by at the 13th-century castle where Museo Leonardiano can be found. This museum has da Vinci’s inventions, including a car, parachute, and helicopter. It’s also where his drawings of wooden models complete with pulleys and gears are preserved.
- Lucca: The beautiful town of Lucca has breathtaking architecture, well-kept walls, and important musical history. Unlike other Tuscan places, Lucca is easily accessible because it is flat. You can visit the entire town in a day, but we highly recommend that you take your time to explore its wonders. It’s also a great base if you plan to travel to north or central Tuscany. Lucca is at the foot of the Apuan Alps with many sights to behold, such as Piazza dell’Anfiteatro and the remains of a 12th-century church of Saints Giovanni and Reparata. The top of the old town walls has become a pedestrian promenade, one of Lucca’s top attractions.
- Florence: Some people will tell you to visit Florence at least once in your life – and we agree! Florence or Firenze, the capital of Tuscany, is one of the most popular Italian cities with about 10 million visitors each year. And who can blame them? This city is like a museum with so many sights within walking distance from one another. From the 115-metre high Duomo (Santa Maria del Fiore) to other churches like the Gothic church Santa Maria Novella and Gothic basilica Santa Croce to the Palazzo Vecchio, these places are worth a visit. Other impressive areas are the Pitti Palace with the Boboli gardens, the Galleria degli Uffizi, and Ponte Vecchio, Tuscany’s famous bridge. Enjoy a gelato while strolling the streets or window shopping. If you’re staying on for dinner then a steak Florentine with a glass of Chianti is a great local experience.
- Siena: A romantic city in Tuscany, Siena has grown to be one of our favourite Tuscan cities. It’s small but filled with captivating medieval buildings. A huge plus is that it is not as crowded as Florence and other popular cities. Piazza del Campo is a good stop and right at the heart of the Siena. The best way to admire one of the greatest European Medieval squares is whilst sipping a cup of coffee. If you have visited plenty of churches in Italy, don’t pass on Duomo di Siena, which has not only a magnificent gothic exterior but also a beautifully mosaic-decorated floor. If you missed the Leaning Tower of Pisa, here’s an alternative: the Torre del Mangia located within the Public Palace in Piazza del Campo with 400 steps to reach the top.
- Pisa: Arriving at the Square of Miracles (Piazza dei Miracoli) will immediately show you the magnificent tower. But don’t just look at it from the ground. Take this once-in-a-lifetime opportunity to climb up to see the fantastic views with your own eyes. Buy your tickets in advance, though. But the Leaning Tower of Pisa is not the only thing that the city offers. It’s also well-known for the Cathedral and Baptistery. You don’t have to go far to see the Museum of Synopses and the Cemetery along the square’s perimeter. We encourage you to take a leisurely walk along the Arno River. From here, you will see the Clock Palace, which will lead you to Piazza dei Cavalieri. It was once where Pisa’s power lay and was later used as the headquarters of the Knights of St. Stephen.
Honourable mentions are:
- San Gimignano: This small-walled hill town is famous for its architecture and the extra efforts in preserving tower houses.
- Poggibonsi: Another town in Siena province, Poggibonsi, is located in central Italy, between Florence and the city of Siena. It’s famous for its beauty and was even named one of the most beautiful cities in Italy. Unfortunately, Poggibonsi was subjected to a ton of destruction for hundreds of years. But it’s still an excellent place to visit with its lovely landscape, rows of vineyards, and the Fortezza Medicea di Poggio Imperiale (Medici fortress).
- Radda in Chianti: Speaking of landscape and vineyards, you will find plenty of these in Radda. Also called Ratti, Radda in Chianti has interesting architecture. The medieval village and castle, along with the town walls and the Porta Fiorentina, are just some of the hotpots to feast your eyes on.
- Gaiole in Chianti: A municipality in the Province of Siena, Gaiole in Chianti is a notable city in the Chianti Classico region. It has the perfect blend of food, sights, and history. Beyond the Chianti Classico wine, Gaiole offers several spots that will leave you awestruck, including the Brioli Castle, which is the biggest winery in Chianti Classico. Aside from castles, there are parish churches and abbeys. The Eroica, now called Strade Bianche, is an important event for cyclists, which started in 1997. It’s a unique race that focuses on enhancing the environmental heritage whilst promoting clean transport and a healthy lifestyle.
For some food choices, pici is a must-try, which is one of the traditional dishes of Siena. Pici is similar to spaghetti, but it’s fatter. Desserts are interesting local snacks like ricciarelli, a biscuit made with almonds.
Meanwhile, for Pisan cuisine, there are simple dishes to enjoy with the best local ingredients like olive oil harvested from the Pisan Mountains. Many dishes here are fish-based, but there are also meats like Pisan steak from a local bovine breed.
Grace Brown’s Favourite Rides in Tuscany
This begins in Florence, an easy road ride for newbies. The challenge ramps up as you head to Vinci, preparing you for the final location, Montaione, a beautiful reward that sits atop a small hill before you return to Florence.
We already talked about Florence and Vinci, but we left Montaione behind. It’s one of those villages that not many people rave about, but it is undoubtedly remarkable on its own. Perched on a high hill, it’s Tuscany’s last frontier. Though it lacks vineyards compared to Chianti, Montalcino, and other nearby towns, Montaione easily makes it up to you with its olive groves, a 27-hole golf course, restaurants, and swimming pools.
Discover Casa Masi, a hidden gem in the area. This rustic restaurant used to be a tobacco warehouse, which was built many centuries ago. Dine here for an exquisite experience, and don’t forget to ask about stories about the furniture pieces in the restaurant. Enjoy a gramigna al pecorino pasta paired with a local Chianti.
Fun Fact: Montaione has some of Tuscany’s priciest villas.
This loop ride follows the beautiful river valleys and gorges north of Lucca in Tuscany. The back half of the ride climbs up through the Alpi Apuane National Park then descends west towards the Mediterranean Ocean. Before going back to Lucca, you will have to cycle south along the coast.
Exploring the area takes you to the Carrara marble quarries by cycling at your own pace. It’s an amazing experience to learn about marble transportation and excavation, with hundreds of quarries taking place in the Apuan Alps since ancient Rome. It’s an epic ride and surprisingly peaceful even in the heat of summer. Take this chance to taste local delicacies as you visit the old town centre, including tordelli Lucchesi, a dish filled with lots of ingredients like pork and beef, chard, pecorino, garlic, nutmeg, and breadcrumbs.
Fun Fact: Quarries along the Marble Mountains or Apuan Alps (Alpi Apuane) produce more marble than anywhere in the world.
Follow the route of the famous Strade Bianche race along “The White Roads of Tuscany”. This route takes the 138km course used for the women’s race, looping out of Sienna in a south-easterly direction.
The 15th Strade Bianche was held on 6 March 2021, starting and concluding in Siena. The “white roads” term refers to the unpaved back roads running amongst the olive groves and vineyards along the pathway. It’s an ideal way of discovering rural Tuscany on your bike but also offers panoramic walking paths. The Strade Bianche race was once called Eroica, an impressive tour that you can take with an e-bike. Two days of cycling will let you enjoy a good speed as you witness the dusty Tuscan while having fun, of course!
Fun Fact: Riders who win three Strade Bianche races will have a section of gravel road named after them.
Pisa – Lucca – Montecatini Terme – Pisa
Here’s a wonderful loop ride that explores the foothills and villages of Pisa, Luca, and the river valleys of Montecatini Terme.
If there’s an excursion that lets you understand the most visited Tuscan cities, Pisa and Lucca, this is it. But let’s not ignore the beautiful spa town of Montecatini Terme, which has an abundance of neo-Gothic buildings, stunning landscapes, and fine food and drink. While in Pisa, don’t forget to take a bite of Cecina, an incredibly thin piece of gluten-free bread. It’s made with chickpea flour, oil, water, black pepper, and a bit of salt. Eat it alone or add a flatbread called schiacciatina. This treat is a must-try!
Fun Fact: The Leaning Tower of Pisa was constructed in 1173 but only finished in 1372, taking almost 200 years or two centuries.
Wine, Food Lovers and Historic Sites Loop
Start in San Gimignano to visit any of the 14 towers and see medieval architecture and masterpieces from the 14th and 15th centuries. You can move on to Poggibonsi and then Radda in Chianti. This tiny town perfectly represents a typical Tuscan medieval plan, sitting atop a 533-metre high hill. Head to Gaiole in Chianti, a town surrounded by cliffs and valleys, before returning to San Gimignano.
Gaiole in Chianti is known as the market centre, so expect to see wine and cultural events in the summer. Seize the chance to visit the Ricasoli castle in the town of Vetrine, which is almost in the same condition as it was in 1478. What’s unique about this castle is its rough oval shape. Plus, it has plenty of open spaces, making it a great stop on your itinerary.
Fun Fact: San Gimignano was once inundated with a total of 72 towers (only 14 remain). Back in the days, the more towers a city had, the more powerful and wealthy it was deemed.
As you can see, there is a biking route for you in Tuscany, no matter what your preferences are. Tuscany is a picture-perfect region of Italy with many opportunities and experiences to immerse yourself in, whether in tourist-famous places like Pisa and Florence to lesser-known areas like Vinci and Poggibonsi.