Sipping on a Negroni in a historic town center, under the Tuscan sun, refreshing yourself after a day’s ride through rolling hills and bucolic landscapes. This could be you soon, but it’s also just a tiny portion of what you’ll experience if you head on this week-long, self-guided bike tour through Tuscany. You’ll discover charming hilltop towns, taste the Chianti wine reminiscent of sour cherries, smell the fragrant olive and fruit trees, and hear the chirp of crickets on warm nights. Starting from the Town of Fine Towers, San Gimignano, you’ll pedal your way through quintessential Tuscan villages, vineyards, and cypress-lined paths, all the way to the remarkable Siena. This is cycling and exploring Italy at its finest.
Spend a week in Tuscany on a self-guided cycling holiday and immerse yourself in the beauty of its countryside! Rural Tuscany is synonymous with undulating green hills dotted with medieval towns, punctuated by cypresses, churches and stone farmhouses. It’s where you’ll find delicious wine and authentic Italian food. With this self-guided tour, you’ll be able to cycle at your own pace, with your own people, and having everything arranged for you—this is a worry-free tour, ideal for those who want to fully focus on just enjoying the trip and taking in everything Tuscany has to offer!
Arrive at Pisa Airport and get transferred to San Gimignano (approximately 1.5 hours). Depending on your arrival time and local arrangements, a local representative will either meet you tonight or tomorrow morning to fit you to your rental bikes (if renting) and hold a welcome meeting. Details will be confirmed for you ahead of your departure. After checking into your accommodation, you will have the rest of the day to explore the local area and get prepared for your first day of cycling!
Accommodation: Three or four-star hotel, guesthouse, or agriturismo
The fascinating town of San Gimignano, known as the Town of Fine Towers, is one of Italy’s prettiest and best-preserved medieval settlements. It’s also famous for its white wine, Vernaccia di San Gimignano, grown in the area. The old town is a UNESCO World Heritage Site, and taking a walk through its narrow streets to fully absorb the Tuscan atmosphere is a must!
Back on the bikes, you’ll descend towards the plains of Colle Val d‘Elsa, passing woodland and cultivated fields on your way to the hilltop town of Casole d‘Elsa. The last few kilometers are challenging, but the views from the top are worth the effort. You’ll have time to explore this authentic medieval town, far from the typical tourist spots of Tuscany. Your accommodation is just outside the walled center, a short walk into town where you can enjoy an evening drink. A great way to end the day is by watching the sunset from the bastions, overlooking the Tuscan hills.
Meals: Breakfast
Cycling: 18 miles / 29 km
Elevation gain: 1,640 ft / 500 m
Accommodation: Three or four-star hotel, guesthouse, or agriturismo
Leaving Casole d‘Elsa, you’ll travel along rolling roads, passing small stone villages scattered throughout the countryside. Parts of the route are on the Via Francigena, an ancient pilgrimage from Canterbury to Rome, leading straight to your accommodation—an ancient medieval village surrounded by vast vineyards, perfect for sampling local wines. A short cycle away, you’ll reach Abbadia Isola.
The fields surrounding Abbadia Isola were once a large swamp that collected rainwater from Monte Maggio. ‘Isola’ refers to the island or the only solid piece of land on which the original ancient hamlet was built. The Abbey of St. Salvatore, founded in the 11th century, was a strategic crossroad on the Via Francigena between Florence, Fiesole, Siena, and Volterra. Now surrounded by flat fields filled with sunflowers in summer, the abbey offers an easy and enjoyable ride from your accommodation.
Meals: Breakfast
Cycling: 19 miles / 31 km
Elevation gain: 1,970 ft / 600 m
Accommodation: Three or four-star hotel, guesthouse, or agriturismo
Today marks the toughest stage of the week, featuring a ride through the NW side of Siena and into the Chianti region. Each uphill struggle will be met with an exhilarating downhill reward, though! The first climb leads to the Castle of Monteriggioni, boasting 13th-century architecture and massive walls steeped in the lore of Dante’s Divine Comedy. Once a defensive bastion against rival Florence, the castle now invites a leisurely stroll through its narrow streets and a cycle around its fortified walls. Pedaling onward, you’ll head towards Castellina in Chianti, cycling through acres of vineyards that signify your arrival in wine country. Castellina is perfect for exploration by foot, offering not only a wealth of wine but also an abundance of Etruscan sites in the area.
Such rich archaeological heritage justifies a visit to the territorial museum for Chianti Senese, showcasing artifacts not just from Castellina but also from neighboring towns like Castelnuovo Berardenga, Gaiole in Chianti, and Radda in Chianti. Leaving Castellina, another 11 kilometers will get you to Radda in Chianti, a medieval gem encircled by formidable defensive walls.
Meals: Breakfast
Cycling: 19 miles / 31 km
Elevation gain: 1,640 ft / 500 m
Accommodation: Three or four-star hotel, guesthouse, or agriturismo
Today’s route will take you on a gentle ride through the Chianti region, passing through oak forests and vineyards. The day begins with a gentle descent past vineyards towards Gaiole in Chianti, where you can take a detour to visit the town. Known as the birthplace of Chianti Classico, Gaiole has a rich history.
In medieval times, Gaiole was one of the three capitals of the Chianti League, along with Castellina and Radda. This hilltop town is surrounded by oak and chestnut forests, as well as vineyards and olive groves. As a former military stronghold, Gaiole is encircled by medieval castles and fortified abbeys. It is also renowned as the birthplace of the “Eroica” (1997), a vintage cycling event that attracts thousands of riders to the region, cycling along the strade bianche. It’s an ideal spot for a long lunch before cycling back to Radda in Chianti.
Meals: Breakfast
Cycling: 19 miles / 31 km
Elevation gain: 1,640 ft / 500 m
Accommodation: Three or four-star hotel, guesthouse, or agriturismo
Kick off the day with a gentle ride through the Chianti region of oak forests and vineyards. The day begins with a gentle descent, with the landscape transitioning from oak forests to cultivated fields as you make your way towards Siena. This region is dotted with castles, which were once defensive systems but are now privately owned by wine producers. Your route will take you past Meleto, San Donato in Perano, and Brolio Castle.
You’ll follow a mix of tarmac and “strade bianche” (gravel roads) as you approach Siena, catching glimpses of bell towers and churches along the way. Entering Siena through the Porta Romana will lead you straight to the heart of the city, Piazza del Campo, where the famous Palio takes place. There will be time to wander through Siena in the late afternoon, visiting the Palio Square and the Duomo, before heading out to dinner for a mouthwatering Tuscan meal.
Meals: Breakfast
Cycling: 25 miles / 40 km
Elevation gain: 1,640 ft / 500 m
Accommodation: Three or four-star hotel, guesthouse, or agriturismo
Today you’ll say ciao to this beautiful part of Italy. You’ll get transferred back to Pisa Airport for your outgoing flight (approximately 1.5 hours), but if you’d like to stay longer and explore the area, just ask us for some recommendations!
Meals: Breakfast
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 (in case there is a detailed list).
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!
Tuscan scenery was awesome! Representatives were excellent. I needed some bike repair at the end of day 4 in Siena and it was done after a single text message with no hassle at all. No errors on the map and easy to follow!
Excellently described and true to the descriptions. A full and thorough briefing at the start of the trip and great directions (map and words) – we never got lost once. Excellent service during the booking process and on arrival, through to the taxi transfers to and from the airport. The ride from Casole D‘Elsa to Abbadia Isola (and for our changed itinerary) through to Monteriggiano was excellent – lovely road through some amazing countryside (though the whole week could be described this way) but we had a cappuccino stop at the restaurant recommended en route. Questions answered promptly and well and nothing was too much trouble. A really excellent trip – so well organised and made easy work (despite the hills & heat) of the beautiful Tuscan countryside. Thank you very much to all the team!
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*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 (in case there is a detailed list).
Fitness and experience
This Tuscany self-guided bike tour is suitable for those who perhaps have only recently gotten into cycling, and there’s an array of accessible, cycle-friendly paths and roads. Still, there will be some days and sections where you’ll have to tackle some ups and downs as well as the occasional steeper climb. This tour is ideal for those with a decent level of fitness, looking for some leisurely rides with occasional (though achievable!) challenges along the way. Generally, you’ll cover around 20 miles (32 km) every day.
Terrain and roads
Here’s a list of the equipment you need to bring:
Dress comfortably and for the weather in clothes you can move in. We suggest bringing clothing appropriate for the season. Layers are best and don’t wear jeans.
Indeed you can! If you don’t own a suitable bike or would prefer to avoid bringing your own to this Tuscany self-guided bike tour, you can rent one with your guides. Rental bikes will be provided with a pannier rack and 1 bag, a phone mount, a water bottle holder, a puncture repair kit, a spare inner tube, a bike lock and a bike pump.
Hybrid bikes (typically Focus Univega Geo or equivalent) or e-bikes (typically Focus Univega Geo e-bikes or similar) are rented out for this tour.
If you choose to bring your own e-bike, on any of departures, please contact us so we can discuss the bike specification and ensure it is suitable for the tour.
Helmets can be provided locally on request. If you would like us to organise this please request a helmet at the time of booking.
A self-guided tour is an independent exploration without a formal guide leading the way. Instead of being part of a group with a tour leader, you will navigate the tour yourself, using resources provided by the operator, such as maps, guidebooks, audio guides, or digital apps.
By going on this Tuscany self-guided bike tour, you’ll have lots of things arranged for you, making your cycling experience a lot less stressful and a lot more enjoyable:
After you get transferred to San Gimignano and once you’ve talked to a local representative, the self-guided tour starts! Keep in mind that your guides offer support along the way should you need anything.
Group sizes and pricing
Tuscany self-guided bike tours can be arranged for larger groups. Contact us to make arrangements.
Min. age requirements
If your group has riders under the age of 18, contact us prior to booking to make arrangements.
To get to your Tuscany self-guided bike tour, first you’ll fly into Pisa Airport (PSA). Transfer from the airport to the town of San Gimignano is included in the price of the tour. Please aim to arrive between 9 am and 4 pm, and depart between noon and 7 pm.
Make sure your tour is confirmed and ready to go before making any travel arrangements. Please note that if you make travel arrangements outside the time windows above, there may be an additional charge for your transfers.
Medical and travel protection are mandatory on this adventure. To make your booking and traveling experience as carefree as possible, simply choose Redpoint—the official 57hours insurance partner!
Redpoint tailors their 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.
Once your booking is confirmed and your trip is paid in full, you will be offered to purchase Redpoint’s protection. If you need any help or require more information, let us know and we will be happy to help!
A non-refundable $250 deposit to secure your place is due upon booking. The remaining amount is paid 2 months (60 days) prior to departure. Once the trip is confirmed by the guide, the cancellation policy stated below applies.
If you need to cancel the trip, please contact us in writing. If you wish to transfer a booking to another person, please write to us at least seven (7) days before your trip. Administration charges may arise.
All aspects of the cycling tour were excellent from the initial contact and followup emails back and forth in the months preceding our trip to the details provided at the very start of the trip in San Gimignano. Instructions were clear and the self guided maps and information provided were accurate and relatively easy to follow. Great bikes! Solid, easy to ride and well tuned. We were surprised somewhat to see that the tires provided were slicks instead of tires with some tread. We were a little concerned on the first day when it rained that the roads would be slippery but it wasn’t an issue. Overall, yes, good value for the money.