Bicycle Tours & Trips in Tuscany
Ready to cycle Tuscany? Follow the rivers from Pisa to Lucca, winds through Chianti's vineyards, and maybe pass Leonardo da Vinci's birthplace near Vinci. Check out the medieval town of San Gimignano, and witness cypress-lined roads cutting through Italy's countryside where every hilltop seems to hold a town from centuries past.
10 best bicycle Tuscany tours
Compiled by
MelissaTuscany travel expert at TourRadar
- Bike Across Tuscany - Guided
- Cycle Tuscany
- Bike tour, Tuscany, Italy (guided groups)
- Strade Bianche
- Classic Tuscany - Cycling from Florence to Pisa - Classic Self Guided
- Tour of Tuscany
- Pisa - Florence
- Tuscany guided-Ebiketour | Italy: Highlights of southern Tuscany & Elba | 8 days
- Tuscany
- Tour de Tuscany Italy Cycling Tour – Florence to Pisa
Bike Across Tuscany - Guided
4 Reviews by TourRadar travelers“The knowledge and experience that the company has in this territory is an incredible differential.”
Nilo, traveled in September
The 285km route from Lucca to Florence showcases Tuscany's finest landscapes. Premium bikes handle challenging routes through Chianti wine country. UNESCO sites like Pisa's Square of Miracles and authentic agriturismos provide cultural richness.
Duration 8 days Destinations Lucca, Pisa, Vinci, Colle di Val d'Elsa, San Gimignano, Siena, Florence Age Range All Ages Welcome Distance 117 mi Operator BikesPlus Travel From
- US$2,807
Cycle Tuscany
14 Reviews by TourRadar travelers“Trip of a lifetime. Could not have been any better.”
Walter, traveled in June
Quality Kross bikes with hydraulic brakes carry cyclists through Tuscany's finest routes. Highlights include Leonardo da Vinci's birthplace and historic Fronte della Rocca bakery. Support vehicle assists during 35-84km daily rides, with e-bikes available.
Duration 8 days Destinations Florence, Signa, Empoli, Vinci, Lucca, Borgo a Mozzano, Barga, Castelnuovo di Garfagnana, San Romano, ViareggioSee all destinations Age Range Ages 14+ Distance 149 mi Operator Intrepid Travel From $3,180
20% Off- US$2,544You save $636
Bike tour, Tuscany, Italy (guided groups)
4 Reviews by TourRadar travelers“In September 2017, our group of 4 cyclists did the Umbria bicycle tour with Chain”
Duration 6 days Destinations Florence, San Gimignano, Panzano, Greve in Chianti, Radda in Chianti, Monteriggioni, Siena, Asciano, SI, Montalcino, PienzaSee all destinations Age Range Ages 12+ Operated in English, Italian, French Physical Rating Moderate Distance 105 mi Operator The Chain Gang Cycle Tours From
20% Off- US$2,885
White gravel roads stretch from Radda in Chianti to Siena. A challenging 67km Chianti loop and epic 138km Gran Fondo with 2,093m elevation gain test riders. Medieval villages like Greve and Colle val d'Elsa dot the route, with luxury stays at historic properties.
Duration 6 days Destinations Radda in Chianti, Greve in Chianti, Siena Age Range Ages 18+ Operated in English, Spanish Distance 26 mi Operator Eat Sleep Cycle From
20% Off- US$3,843
Classic Tuscany - Cycling from Florence to Pisa - Classic Self Guided
6 Reviews by TourRadar travelers“We completed a self-guided route and it felt like a completely independent trip, but we never had to consider a single logistical hurdle.”
Jeff, traveled in May
The 326km route through Tuscany's renowned wine country features daily 500m climbs. Paths wind from Florence's Ponte Vecchio through Chianti vineyards to medieval San Gimignano. Premium bikes handle challenging terrain between historic cellars and Renaissance villas.
Duration 8 days Destinations Florence, Radda in Chianti, Siena, San Gimignano, Vinci, Lucca, Pisa Age Range All Ages Welcome Distance 103 mi Operator BikesPlus Travel From
20% Off- US$1,887
Medieval Radda leads to UNESCO-listed Siena hills on routes spanning 19-83km daily. Historic Volpaia's wine cellars, challenging 'Le Strade Bianche' sections, and traditional cuisine at select locations highlight the journey.
Duration 7 days Destinations Radda in Chianti, Greve in Chianti, Volpaia, Gaiole in Chianti, Siena, Bagno Vignoni Age Range Ages 18+ Operated in English, Spanish Physical Rating Moderate Distance 54 mi Operator Eat Sleep Cycle From
20% Off- US$4,309
Rolling hills and historic paths stretch from Pisa to Florence on this cycling adventure. Lake Massaciuccoli's panoramic roads, Montecarlo's vineyards, and medieval Montevettolini highlight the 210km journey. Premium lodging includes stays at Hotel Repubblica Marinara.
Duration 7 days Destinations Pisa, Lucca, Montecatini, Vinci, Pistoia, Florence Age Range All Ages Welcome Operated in English, German Physical Rating Moderate Distance 72 mi Operator Eurobike From
20% Off- US$1,280
Rolling hills of Tuscany unfold on this premium e-bike tour from Pisa through Maremma National Park. Routes pass Scansano's vineyards, trace Monte Argentario's coastline, and reveal Elba's hidden bays. Professional guides lead moderate 29-mile daily rides.
Duration 8 days Destinations Pisa, Natural Park of Maremma, Tuscany, Scansano, Monte Argentario, Grosseto, Elba Age Range Ages 18+ Operated in English, German Physical Rating Moderate Distance 287 mi Operator Terranova Touristik From
20% Off- US$8,311
Pedal from Castellina through Chianti's terraced vineyards to Florence, crossing the famous Ponte Vecchio. Ride along Lucca's medieval walls, then follow Lake Massacciuccoli to Pisa's UNESCO Piazza dei Miracoli and its Leaning Tower, with a stop at fortified Monteriggioni.
Duration 8 days Destinations Montecatini, Pisa, Casciana Terme, San Gimignano, Siena, Castellina in Chianti, Florence Age Range All Ages Welcome Operated in English, German Distance 111 mi Operator Eurobike From
20% Off- US$1,397
Duration 8 days Destinations Florence, San Miniato, Vinci, Lucca, Pisa Age Range Ages 18+ Operated in English, German, Italian Physical Rating Moderate Distance 59 mi Operator Tour de Vines From
20% Off- US$4,653
What people love about Bicycle Tours in Tuscany
- Bike Across Tuscany - Guided
Great trip ... excellent guides and fantastic scenery... would highly recommend Cycle Europe!
- Cycle Tuscany
Trip of a lifetime. Could not have been any better. Would recommend to others.
- Bike tour, Tuscany, Italy (guided groups)
In September 2017, our group of 4 cyclists did the Umbria bicycle tour with Chain Gang tours. There were other riders on the tour as well so we were 9 riders in total. We met in Orvieto and were transported to the small tour where the tour began. As we cycled through small towns and pleasant countryside, it became clear our guide was very knowledgeable about the history of the country. We were seeing beautiful country but also leaning about its past as we travelled through it. The hotels and meals were first rate. The guide and his assistant (van driver) made sure our bikes were in good working order each day. We saw beautiful countryside, had great meals and enjoyed great company. What could be better than that.
What our customers ask about Bicycle Tours & Trips in Tuscany
What are the most scenic cycling routes in Tuscany?
The UNESCO-listed Val d'Orcia region between Pienza and Montalcino presents classic Tuscan landscapes. The route connecting Florence and Siena winds through the Chianti wine country while Pisa takes cyclists past medieval villages and olive groves. The San Gimignano to Volterra stretch offers views of hilltop towns and ancient ruins. One TourRadar traveler shared: "The ride through Val d'Orcia was absolutely stunning - cypress trees rolling hills and medieval villages made every pedal stroke worthwhile."
What is the best time of year for cycling in Tuscany?
The cycling season spans April to October with peak conditions in May June and September. Spring brings wildflower-covered hills around Montepulciano and Pienza while September offers prime vineyard views during harvest. July and August can be challenging with temperatures in inland areas like Siena often reaching above 30°C (86°F). As noted by a TourRadar traveler: "We went in September and had perfect weather for cycling - warm sunny days but not too hot with cool mornings perfect for riding."
What type of accommodation can I expect on Tuscany bicycle tours?
The accommodations range from boutique hotels to restored farmhouses known as agriturismos. Properties like the Grand Hotel Croce di Malta in Montecatini Terme and the converted monastery Certosa di Maggiano in Siena showcase local architecture. The Relais Il Chiostro in Pienza offers rooms overlooking Val d'Orcia. As one TourRadar traveler mentioned: "The hotels were carefully chosen for their character and location especially the beautiful agriturismo in the Chianti region with its amazing views."
What level of cycling experience is needed for Tuscany bicycle tours?
Tuscany's terrain calls for moderate fitness and basic cycling skills. The Florence to Pisa route offers gentler riding while Chianti and Val d'Orcia present more challenging elevations. Daily routes typically cover 35-55km with elevation changes of 500-1000m. According to a TourRadar traveler review: "You don't need to be a pro cyclist but some hill training before the trip definitely helped especially for the climbs around Montalcino."
What's included in typical Tuscany bicycle tour packages?
Standard tour packages cover accommodation daily breakfast luggage transfers route maps GPS navigation and bike support. Higher-end tours particularly in Chianti add wine tastings and food experiences. Accommodations like the Hotel Palazzo in Pistoia and Grand Hotel Croce di Malta represent typical lodging options. As one TourRadar traveler noted: "Everything was well-organized from the bike fitting to luggage transfers allowing us to focus on enjoying the rides and scenery."
What are the dining arrangements on Tuscany bicycle tours?
Tours provide breakfast at partner hotels such as the Grand Hotel Croce di Malta or Hotel Italia in Siena. Lunch and dinner spots remain flexible letting cyclists discover local establishments. Select tours feature wine tastings in Chianti and Montalcino or planned group meals at family-run trattorias. A TourRadar traveler commented: "The flexibility to choose our own restaurants was perfect - we discovered amazing local places in every town especially in Pienza and Montepulciano."