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
- Bike tour, Tuscany, Italy (guided groups)
- Cycle Tuscany & Chianti
- Cycle Tuscany
- Postcard Southern Tuscany - Cycling Cortona, Montalcino, Siena - Classic Self Guided
- Strade Bianche
- Tuscany guided-Ebiketour | Italy: Highlights of southern Tuscany & Elba | 8 days
- Tuscany guided-Ebiketour | Italy: Highlights of southern Tuscany & Elba | 8 days
- Pisa - Florence
- Tour of Tuscany
Bike Across Tuscany - Guided
“Excellent guides and fantastic scenery... would highly recommend Cycle Europe!”
Kevin, traveled in April
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$2,815
Bike tour, Tuscany, Italy (guided groups)
“stunning scenery (photo op delight!) and great local food and wine”
Paul, traveled in September
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 273 mi Operator The Chain Gang Cycle Tours From
- US$2,932
Cycle Tuscany & Chianti
“The trip was very organized and well run. And of course we were in Tuscany!”
Stephen, traveled in April
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, Radda in Chianti, Gaiole in Chianti, Siena, Asciano, SI, Monteriggioni, Colle di Val d'Elsa, San Gimignano, Gambassi Terme, San MiniatoSee all destinations Age Range Ages 15+ Distance 127 mi Operator Intrepid Travel From
- US$3,195
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+ Physical Rating Moderate Distance 149 mi Operator Intrepid Travel From
- US$3,795
Postcard Southern Tuscany - Cycling Cortona, Montalcino, Siena - Classic Self Guided
“We loved everything about our self-guided tour. The itinerary kept us on less-traveled roads as much as possible.”
kathysteinberger, traveled in July
Routes between Cortona and Siena cover 280-344km through UNESCO Val d'Orcia. Daily climbs reach 3,000ft while visiting Montepulciano's cellars and Pienza's Renaissance streets. Premium titanium bikes ensure optimal performance.
Duration 8 days Destinations Cortona, Lake Trasimeno Regional Park, Montepulciano, Pienza, Monticchiello, Trequanda, Montalcino, San Quirico D'orcia, Bagno Vignoni, Siena Age Range All Ages Welcome Distance 103 mi Operator BikesPlus Travel From
- US$1,723
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
- US$3,853
Duration 8 days Destinations Pisa, Natural Park of Maremma, Tuscany, Scansano, Monte Argentario, Orbetello, Elba Age Range Ages 18+ Operated in English, German Physical Rating Moderate Distance 281 mi Operator Terranova Touristik From
- US$8,333
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
- US$8,333
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
- US$1,284
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 Tuscany, Greve in Chianti, Volpaia, Gaiole in Chianti, Radda in Chianti, Siena, Asciano, SI, San Quirico D'orcia, Bagno Vignoni, PienzaSee all destinations Age Range Ages 18+ Operated in English, Spanish Physical Rating Moderate Distance 113 mi Operator Eat Sleep Cycle From
- US$4,320
What people love about Bicycle Tours in Tuscany
- Bike Across Tuscany - Guided
Great trip ... excellent guides and fantastic scenery... would highly recommend Cycle Europe!
- Bike tour, Tuscany, Italy (guided groups)
Chain Gang focus on small group cycling holidays that take in stunning scenery (photo op delight!) and great local food and wine. Knowledgeable guides take you off the beaten track to some delightful towns and villages where you can sample great food or patter around to your hearts content. The accommodation along the way is beautiful, and not the sort of thing you could easily find yourself. Luggage is all taken care of and you just need to cycle to your nights accommodation. Bikes, helmets, jackets etc... are all supplied - just bring yourself. All in all, some of the best cycle tours we've done are with this group - no wonder so many people keep coming back. Highly recommended!
- Cycle Tuscany & Chianti
The Cycling Tour of Tuscany trip balances the athletic aspect of cycling with the sightseeing / food / wine highlights of Tuscany.
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."