A self-guided bike tour through the heart of Tuscany might just be the best way to experience this wonder of a region. You’ll be riding through its spectacular landscapes for a week, experiencing everything from lush vineyards and olive orchards to lovely cobblestone streets and vibrant cities. Your guides organized terrific lodgings as well as baggage transfers, breakfast, detailed routes, and the best local recommendations. For a carefree holiday, it doesn’t get much better than this—explore Tuscany at your own pace and with your own people.
Make your way to Pienza, a wonderful renaissance town in Tuscany. Pienza is a remarkable example of renaissance architecture and it’s truly a treat to just stroll around its cobblestone streets. After the bike fitting, go for an optional short test ride to Montepulciano. Retreat to your charming hotel.
Accommodation: Hotel Rutiliano or Piccolo Hotel La Valle
Distance: 35 km / 22 miles
Start your day with a long descent down rolling green pastures of the Val d’Orcia to Bagno Vignoni, an ancient village in the heart of Tuscany. Thanks to Via Francigena, an old route which pilgrims once used during antiquity to get to Rome, the thermal waters of Bagno Vignoni have been enjoyed since Roman times. Here you’ll find the Square of Sources, a tank containing water coming from the underground aquifer.
Along the way you’ll face the challenging uphill to Castiglione d’Orcia, with the imposing Rocca di Tentennano fortress. After a quick break, enjoy a long and flowy downhill to the Romanesque abbey of Sant’Antimo that dates back to the time of Charlemagne—maybe have a coffee or a lunch break. For your last effort of the day, climb a gentle uphill to Montalcino, an Etruscan village and hilltown famous for the Brunello wine. Return to your accommodation in Pienza.
Accommodation: Hotel Rutiliano or Piccolo Hotel La Valle
Distance: 70.6 km / 44 miles
Elevation: +1,391 m / +4,564 ft | -1,396 m / -4,580 ft
Optional: Longer ride to San Filippo (100 km / 62 miles)
Today you’ll witness the typical postcard scenery of Tuscany, Italy’s favorite region. Following a picturesque road, ride by Castelmuzio and Trequanda. Afterwards, travel through the fascinating area called La Crete, where you’ll find the traditional Tuscan landscapes of rolling hills, cypress trees, and lone farmhouses. Verdant hills also give way to little domes of clay and you’ll come across almost lunar landscapes of chalk cliffs and gullies.
Continue cycling and reach Lucignano, a small village that’s a prime example of medieval urban planning due to its system of elliptical rings, still intact. Final destination is the Castello di Gargonza, a magical castle surrounded by lush woods. Dinner today is included.
Accommodation: Castello di Gargonza
Distance: 56 km / 35 miles
Elevation: +978 m / +3,209 ft | -951 m / -3,120 ft
Optional: Longer ride via Asciano
Pedaling north, whisk past a pair of typical southern Tuscany towns and make a stop at Castelnuovo Berardenga, the gate to Chianti Classico region. Pass through countless vineyards and continue down to Castello di Brolio winery, home of Barone Ricasoli and its world-renowned wine.
After a few more miles, you’ll get to Gaiole. Stop here for a light lunch. Then it’s time to face the climb to Badia a Coltibuono—when it gets difficult, think of the beautiful downhill to Radda in Chianti that you’ll enjoy! Then it’s the last 10 km up and down to get to your palazzo hotel with a spa.
Accommodation: Hotel Palazzo Squarcialupi Castellina in Chianti
Distance: 64.3 km / 40 miles
Elevation: +1,156 m / +3,793 ft | -1,102 m / -3,615 ft
Optional: Longer ride to Monte Luco
By pedaling to San Gimignano, you’ll pass by countless vineyards. After going by San Donato in Poggio, Tavarnelle in Val di Pesa, and Barberino, you’ll be in the Florentine Chianti. Soft, colorful, and rolling hills of vineyards and sunflowers provide the perfect backdrop to pre-Roman Etruscan remnants.
Along the way, you’ll see San Gimignano’s “medieval skyscrapers” in the distance. You’ll have plenty of time to wander through cobblestoned streets, window shop, and buy some Tuscan souvenirs to take home. To get back to Castellina in Chianti, get ready for a beautiful uphill from Poggibonsi.
Accommodation: Hotel Palazzo Squarcialupi Castellina in Chianti
Distance: 76 km / 47.5 miles
Elevation: +1,236 m / +4,055 ft | -1,236 m / -4,055 ft
Start your day with a long downhill to Monteriggioni, a beautiful town completely walled in! Only 80 people reside within the picture-perfect round turreted walks that crown the hilltop. After passing Casole d’Elsa, continue pedaling through the vineyards and finally arrive in Siena!
Siena is a medieval city with beautifully preserved Gothic architecture. The entice city was built around the Piazza del Campo, and here you’ll have enough time to shop while exploring many hidden medieval walkways. Go visit the shell-shaped square where the Palio horse race is run and enjoy a glass of Tuscan wine at sunset.
Accommodation: Hotel STR in Siena
Distance: 73 km / 45.6 miles
Elevation: +1,068 m / +3,504 ft | -1,294 m / -4,245 ft
After breakfast at your final hotel, the tour comes to an end. Leave your rental bikes, catch a flight, or continue your journey!
Please note that accommodations are subject to availability and it may not be possible to book the exact accommodations listed day-by-day in the itinerary.
Also note that your chosen dates for the tour are not guaranteed until confirmed by the guide. If the guide is unable to secure your preferred dates/accommodation, you’ll get a full refund!
Included:
Add-ons (pricing shown at checkout):
Not included:
To join this self-guided bike tour in Tuscany, you have to be in great shape. There are lots of hilly areas and climbs on this trip and you have to be able to cover these distances. You’ll be cycling 5 or 6 days in a row, covering anywhere between 35-76 km (22-47.5 miles), though you can extend your daily trips. Elevation gains and distances are noted day-by-day in the itinerary above, but you can expect climbing up to 1,391 m (4,564 ft) per day.
Want to see what else is there in the area? Discover more Tuscany bike tours here!
This is a list of clothing & footwear we recommend you bring:
Miscellaneous
First aid kit
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Yes, you can add a bike rental to your booking at checkout. These are your options:
Self-guided tours are perfect for those who enjoy exploring on their own terms—at their own pace, and with the company they choose. By joining this self-guided Tuscany bike tour, we take care of:
Rather than joining a guided group, you’ll navigate the tour yourself, using resources provided by the tour operator. For a hassle-free journey with everything arranged for you in advance, there’s no better option!
As a self-guided tour is built around your preferred travel dates, your guide will take care of arranging accommodations and details after you book. Note that exact accommodations and dates might shift slightly, so don’t make any travel arrangements until the details of your adventure are confirmed.
Group sizes and pricing
Self-guided bike tours in Tuscany can be arranged for larger groups. Contact us to make arrangements.
Min. age requirements
If your group has hikers under the age of 18, contact us prior to booking to make arrangements.
The price for this Tuscany bike tour is based on twin-share rooms, but a single occupancy room can be arranged at an additional fee. You can add it to your booking at checkout.
The starting point of your self-guided bike tour in Tuscany is Pienza. To get there, the nearest airports are Rome Fiumicino (FCO) and Florence Airport (FLR). It’s up to you whether you’d like to rent a car to reach Pienza, the starting point of your tour, or you’d like to use public transport. Driving with a car takes between 1.5-2.5 hours to Pienza, depending on where you land.
For the public transport option, after landing you have to reach Chiusi. The easiest option would probably be to take the train. Once in Chiusi, you can take a bus or a taxi to Pienza, the starting point of your self-guided bike tour in Tuscany.
We highly recommend that you cover all your bases with insurance. To make your booking and traveling experience as carefree as possible, you’ll be offered to simply insure your trip with Redpoint at checkout.
Redpoint—the official 57hours insurance partner—tailors protection packages for adventure travel, offering a comprehensive travel program, even in remote locations! Trip cancellation, natural disasters, pandemic coverage, medical evacuation, primary medical expenses—regardless of the travel interruption that may happen, Redpoint will have you covered.