March -Oct

3 & 4 Hotels

€ 1650

Road Bike Disc

€ 330

Electric Road Bike

€ 460

Transfer Pisa Airport

€ 100

Transfer Florence Airport



Tuscany - Chianti

From: 1,650


Lucca-Florence-Siena Road bike

Self-guided Lucca-Florence-Siena road bike tour.
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Lucca – Florence – Siena self-guided tour in Tuscany

Your cycling adventure starts in Lucca. Lucca is a wonderful ancient town right in the center of Tuscany. To experience Tuscany at its finest, don’t forget to experience all the major sights. Besides the big history and the art of Lucca, Florence, Siena, and Pisa. This cycling tour also will take you all the way through the enchanting Tuscan countryside over gentle colorful hills, great climbs, and descents. Tuscany is very much a diversity between very different areas, expressed in their traditions and also their food and wine. You will have the chance to taste the best of them, from the hills in Lucca to the Chianti, until Montalcino!

Chianti and Eroica

The Chianti and Eroica part of this trip is on every cyclist’s bucket list! When cycling in the Chianti, you find plenty of fascinating historic villages such as Panzano, Radda in Chianti, and Gaiole. In Gaiole, you discover the permanent circuit of the Eroica, a cycling event with classic racing bikes that takes place every year on the first Sunday in October with characteristic dirt tracks. The Eroica route takes you across Chianti Classico to Brolio Castle, the jewel of the estates owned by the Ricasoli family, with magnificent panoramas and excellent wines. If you haven’t visited a winery there will be excellent opportunities in the Chianti area.

Jump on your road bike and enjoy Lucca – Florence – Siena in Italy

  • The medieval town of Lucca; Lucca is “the town of 100 churches”
  • Beautiful beaches and the towns of Forte dei Marmi and Viareggio
  • Florence or Firenze: the birthplace of the Renaissance and capital of Tuscany world famous for its art and Italian culture
  • Lucca and its city walls (perfect for cycling)
  • Fantastic scenery, perfect roads, and fine food make Italy a road cycling paradise
  • 3* and 4* hotels where you can relax
  • Visit the cathedral of Siena (Duomo di Siena)
  • Radda in Chianti, enclosed in its medieval walls, is one of Chianti’s most beautiful villages
  • The village of Montalcino, steeped in history and full of wine bars and shops
Day 1
Check in
Independent arrival in Lucca and settling into the hotel. Lucca can easily be reached by local trains or buses from Pisa and Florence, where Tuscany's main airports are. Private minibus transfers from the airports can be arranged on request.
Day 2
Monte Serra and Pisa - 89 km
After the briefing in the shop in the historic city center of Lucca, you set off for an enjoyable ride with two climbs, Mount Serra and Mount Pitoro, both used by many professional cyclists (Cipollini, Bartali, Basso, Ulrich, Riis, Sorensen, etc.) for their winter training. The first reaches an altitude of 90m , including almost a kilometer with an 18% gradient; the second climbs steadily up to 224m where the delightful panorama takes in Lake Massaciuccoli and the sea. The mandatory stop of the day is, of course, Pisa and the souvenir photo with the bicycle under the Leaning Tower is a must. Accumulated climb: 2186m
Day 3
The coast of Versilia - 91 km
From Lucca, the obligatory excursion takes you along the Versilia coast through vineyards and olive groves across the charming hills separating the city from the sea to Camaiore and Pietrasanta, known as the Little Athens, at the foot of the Apuan Alps where the fine white "Carrara" marble used for building and to create the world's most famous statues is quarried. It is home to many sculptors (Botero is the most famous today), attracted by the ability of a number of small companies to produce statues in marble and bronze. When you reach the coast with its beautiful beaches and the towns of Forte dei Marmi and Viareggio, don't miss a visit to one of the beach restaurants for a swim (season permitting) and spaghetti with seafood. Accumulated climb: 600m
Day 4
Pinocchio and Pizzorna - 80 km
Did you know that Collodi, Pinocchio's village, is near Lucca? You climb up for 400 m to Matraia, then from there, go downhill along an undulating panoramic road for about 12km to Collodi, where a photo under the giant wooden statue of the puppet is obligatory. This is the start of the climb of about 700m up the Trebbio, followed by a delightful ride down to Bagni di Lucca, famous for its spa muds and the perfect place for a snack at the Circolo dei Forestieri or one of the city center bars. Accumulated climb: 2331m
Day 5
Lucca - Florence - 101 km
The journey is mostly through the countryside, first on the olive oil and wine routes in the DOC areas of Colline Lucchesi and Montecarlo. The local roads take you through small towns, past rural churches, farms, and wineries to Montecarlo, a medieval village at the top of a rolling green hill famous for its wines. Your escape in the countryside continues through the magical land where Leonardo da Vinci was born and developed his genius. Montalbano and Vinci, through gentle hills and classic Tuscan scenery, the venue for this year's cycling world championships in September. And then further south towards Montelupo Fiorentino to Signa, traversing the Parco Mediceo around Poggio alla Malva, where you can enjoy spectacular views of the Arno and Pesa valley as far as Chianti as you rest between vines, olive groves, and ancient ruins. You are very close to Florence; once arrived at your destination you abandon the bikes and pretend to be "normal" tourists for a while as you explore the countless courtyards, squares, palaces, museums, churches, markets, and boutiques the city has to offer. Accumulated climb: 839m
Day 6
Gran Fondo Firenza - 95 km
Today's excursion, the middle stage of the Florence Granfondo, takes you through an enchanting hilly landscape with two climbs of more than 800m and a further two of about 400m each. The Mugello area is famous for pastures and knife production. The small town of Scarperia is worth a visit. Accumulated climb: 1600m
Day 7
A rest day is essential to get your energy back and is the perfect occasion for a wonderful visit to the city of Florence. But if you prefer going for a ride, you have prepared an itinerary to make you happy.
Day 8
Florence - Siena 84km
It won't be easy to abandon Florence, but Chianti is awaiting you with a completely different landscape, with some hilly areas, but also others with woods and vineyards stretching to the horizon and a number of climb up through higher almost mountain-like hills.  If you haven’t already visited a winery, then this and the next itinerary are still excellent opportunities.  In Chianti, you can still find fascinating historic villages such as Panzano, Radda in Chianti, and Gaiole, to name just a few of the places worth visiting.  In Gaiole, you encounter the permanent circuit of the Eroica, a cycling event with classic racing bikes that takes place every year along the region’s characteristic dirt tracks, evoking the bicycle racing of long ago with its purity of intention and contact with nature.  The Eroica route takes us across Chianti Classico to Brolio Castle, the jewel of the estates owned by the Ricasoli family, with magnificent panoramas and excellent wines.  You ride down through the vines towards Siena which appears on the horizon, a postcard of presentation for this magnificent city. Accumulated climb: 1279m
Day 9
The tour of Chianti Classico Gallo Nero 104km
The first tour of the Siena area crosses the south of Chianti. There are no great climbs, but a constant series of ups and downs which you can feel in your legs at the end of the day.  You ride through the vineyards of Chianti Classico, the world’s most famous wine for excellent quality and the unmistakable black cockerel logo. Along the route, there are numerous small villages such as Castelnuovo Berardenga, Castello di Brolio, Gaiole, Radda, and Castellina. At Gaiole, a visit to the Eroica shop with its extraordinary collection of classical bikes is a must, while Radda in Chianti, enclosed in its medieval walls, is one of Chianti’s most beautiful villages, together with Castellina in Chianti.  We recommend you visit the Chianti Classico Museum and Enoteca Porciatti wine bar and shop in Radda, perhaps for a snack with traditional products, then the Castellina ice-cream shop in the center of the village with the same name. For a wine tasting, a visit to the Enoteca Fonterutoli wine bar and shop, 4km after Castellina in Chianti, is mandatory. Accumulated climb: 1922m
Day 10
Montalcino 97 km
The day’s excursion heads south towards the clay hills of Siena. You often seem to be riding through a moonscape, the vegetation is different, but there is no shortage of olive groves and vineyards.   You cross the area famous for producing Brunello wine, then after a brief but steep climb, come to the village of Montalcino, steeped in history and full of wine bars and shops. Impossible to offer advice on where to go for a tasting as all the wine is good here. Just go into the wine bar that appeals to you most and ask what they recommend. After Montalcino, you come to Buonconvento, another splendid village where, even if you don't want to actually stop, it is still worth entering inside the walls and visiting it by bike. Accumulated climb: 1866m
Day 11
San Gimignano 96 km
You then head north to the Castle of Monteriggioni, still with much of the 13th-century structures. A photo and a visit to the walkways along the walls are mandatory.  You continue to San Gimignano, a UNESCO World Heritage Site, where it is worth lingering to visit the town center enclosed in its walls with its characteristic towers. Here the typical wine is Vernaccia, one of the few whites in an area dominated by reds. In the city center, there are numerous wine bars and shops where you can enjoy a tasting, while the Dondoli ice-cream shop in Piazza della Cisterna has won the prize for the world's best ice cream. Accumulated climb: 1247m
Day 12
Departure day
Time to say goodbye, a good flight back home or a pleasant stay in Italy

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  • All prices are based on double rooms
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  • 3* and 4* Hotels
  • All breakfast
  • Gps
  • Luggage transfer between hotels
  • Assistance number
  • Briefing in Lucca
  • Transfer
  • Lunch and dinner
  • Single room + €545
  • Road bike Wilier GTR Disc €330
  • E Road bike Wilier €460
  • Transfer from Pisa airport or railway station to Lucca €100
  • Transfer from Florence airport/railway station to Lucca € 130
  • Transfer from Siena to Pisa Airport/railway station €220
  • Transfer from Siena to Florence airport/railway station € 180
  • The third-person reduction is 30%




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