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
- Classic Tuscany - Cycling from Florence to Pisa - Classic Self Guided
- Postcard Southern Tuscany - Cycling Cortona, Montalcino, Siena - Classic Self Guided
- Luxe VIP ~ Montepulciano (Italy) Guided Coach-Cycle (All Inclusive)
- Tour of Tuscany
- Italy: Val d’Orcia by E-Bike & Tuscan Wines 🍷🚴 in 3 DAYS
- Tuscany guided-Ebiketour | Italy: Highlights of southern Tuscany & Elba | 8 days
- Tuscany guided-Ebiketour | Italy: Highlights of southern Tuscany & Elba | 8 days
- Tour de Tuscany Italy Cycling Tour – Florence to Pisa
- Tuscany | Italy | Guided E-bike tour | scheduled departures
- Cycle Tuscany & Chianti
Classic Tuscany - Cycling from Florence to Pisa - Classic Self Guided
“These are adventures that you will have for a lifetime. Do your homework and you will have a trip of a lifetime.”
RobertDunn, traveled in July
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, Greve in Chianti, Radda in Chianti, Siena, Monteriggioni, San Gimignano, Vinci, Lucca, Pisa, Massaciuccoli Age Range All Ages Welcome Distance 120 mi Operator BikesPlus Travel From
- US$1,824
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$1,661
Duration 10 days Destinations Montepulciano, Tuscany, Val d'Orcia, Pienza, San Quirico D'orcia Age Range Ages 18+ Physical Rating Moderate Distance 168 mi Operator Climbing Mountains From
- US$16,153
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$4,165
Duration 3 days Destinations Buonconvento, Montalcino, Tuscany, Pienza, San Quirico D'orcia, Bagno Vignoni, Montepulciano Age Range Ages 12+ Physical Rating Easy Distance 84 mi Operator Aborigen Tours From $1,199
10% off- US$1,079
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
10% off- US$8,035
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
10% off- US$8,035
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
10% off- US$4,510
Duration 8 days Destinations Pisa, Scansano, Natural Park of Maremma, Orbetello, Monte Argentario, Elba Age Range Ages 18+ Operated in English, German Physical Rating Moderate Distance 230 mi Operator Terranova Touristik From
10% off- US$3,260
Cycle Tuscany & Chianti
“Beautiful landscapes. Not too tough, not too easy.”
Leticia, 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
10% off- US$3,195
What people love about Bicycle Tours in Tuscany
- Classic Tuscany - Cycling from Florence to Pisa - Classic Self Guided
This self-guided tour is well designed and planned. The RideWithGps directions are clear in every details. The everyday route and ride length is good, not too hard or too long. They provided a battery bag to hang on the bike. It worked well and allowed me to connect my battery pack to the phone. One suggestion is to deliver the luggage to the hotel earlier, e.g. 1pm or 2pm, instead of 3pm. Because you might arrive the hotel earlier and need to shower and change. I enjoyed the ride through out. Thank you.
- Postcard Southern Tuscany - Cycling Cortona, Montalcino, Siena - Classic Self Guided
From beginning to end, Cycle Europe was fantastic. The pre-planning and communication was incredible. The bikes were titanium bikes, with quality components. The sent staff members to expertly fit the bikes, the routes they planned was perfect, and the hotels were fabulous. On top of everything else, they were willing to help us for our entire vacation. They helped set up a cooking class for us in Lucca, helped arrange a special ceremony for our parent's 50th anniversary, and helped arrange our private transfer. They were really amazing.
- Cycle Tuscany & Chianti
Trip of a lifetime. Could not have been any better. Would recommend to others.
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."