Bicycle Tours & Trips in Tuscany
4.6 stars on(9,268 reviews)- Choose from 13 Tuscany tours
- 26 verified reviews from TourRadar travelers
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10 best bicycle Tuscany tours
Compiled by
MelissaTuscany travel expert at TourRadar
- Cycle Tuscany
- Bike Across Tuscany - Guided
- Classic Tuscany - Cycling from Florence to Pisa - Classic Self Guided
- Strade Bianche
- Tuscany guided-Ebiketour | Italy: Highlights of southern Tuscany & Elba | 8 days
- Tour of Tuscany
- Postcard Southern Tuscany - Cycling Cortona, Montalcino, Siena - Classic Self Guided
- A Taste of Tuscany Cycling
- Picture book Tuscany with Charm - Between Brunello and Chianti 8 Days
- Tuscany with charm 8/7
Cycle Tuscany
14 Reviews by TourRadar travelers“Great experiencing the local culture.”
Edward, traveled in May
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, Vinci, Lucca, Barga, Garfagnana, Pisa Age Range Ages 14+ Distance 87 mi Operator Intrepid Travel From
- NZ$4,375
Bike Across Tuscany - Guided
4 Reviews by TourRadar travelers“The prompt responses we had up front and the attention to detail during the trip was fantastic.”
Frank, traveled in August
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
- NZ$4,649
Classic Tuscany - Cycling from Florence to Pisa - Classic Self Guided
6 Reviews by TourRadar travelers“The RideWithGps directions are clear in every details. I enjoyed the ride through out.”
kehchang, 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
- NZ$3,261
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
- NZ$6,640
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
- NZ$14,361
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
- NZ$7,445
Postcard Southern Tuscany - Cycling Cortona, Montalcino, Siena - Classic Self Guided
2 Reviews by TourRadar travelers“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, Val d'Orcia, Montalcino, San Quirico D'orcia, Bagno Vignoni, Siena Age Range All Ages Welcome Distance 75 mi Operator BikesPlus Travel From
- NZ$2,969
Tuscan vineyards beckon cyclists from Chianciano Terme to historic Montepulciano, passing Lake Chiusi and truffle-rich forests near Cetona. The scenic Sentiero della Bonifica leads to Lake Montepulciano nature reserve, continuing through Val d'Orcia's plains to Roman baths at Bagno Vignoni. Wine tasting and thermal spa visits enhance daily routes.
Duration 8 days Destinations Chianciano Terme, Radicofani, Sarteano, Montepulciano, Pienza, Val d'Orcia Age Range Ages 13+ Physical Rating Moderate Distance 52 mi Operator Exodus Adventure Travels From
- NZ$3,018
Duration 8 days Destinations Florence, Passignano sul Trasimeno, Montepulciano, Siena, Radda in Chianti Age Range Ages 16+ Operated in Only: German Physical Rating Moderate Distance 138 mi Operator ASI Reisen From
- NZ$2,937
Daily routes of 50-55km wind through iconic Tuscan landscapes. Riders pedal from Montecatini Terme through Vinci's historic center, along Lucca's walls, and into Chianti wine country. Premium accommodations offer wellness facilities.
No departure dates availableDuration 8 days Destinations Montecatini, Vinci, Pisa, Casciana Terme, San Gimignano, Siena, Florence Age Range All Ages Welcome Operated in English, German Distance 133 mi Operator Eurobike
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."