Pedal across the Tuscan countryside on this unforgettable 6-day journey.
Tuscany is the stuff of fairy tales; given to warm climates and warmer people, lush vineyards that spill onto the hillsides, and a poetic charm that stays with us. To see this area from the seat of a bike is legendary. Our journey takes us to the finest hill towns in Tuscany to savor traditional cuisine and taste wines as we ride among centuries-old fortified towns, villas and palazzi.
Our destinations range from the Renaissance town of Pienza, to the tree-lined hills of Crete Senesi and, finally, to lively Siena. We bike approximately 40 miles a day through rolling hillsides, our views filled with forests and cypress trees. Our local guides show us Italy’s most authentic side, leading us through charming villages to local artisans, and providing us with historical background along the way. Cycling along the countryside is the perfect opportunity to enjoy the best of Tuscany.
- Explore the lush hillsides of Tuscany on a fully-supported bike tour
- Pedal past scenic vineyards, Renaissance towns, and beautiful pastures
- Enjoy fresh cuisine and taste Italy’s famed wines
- Ride up to 43 miles a day, with ample opportunity to explore and soak in the views
From lovely Pienza to charming Bagno Vignoni.
Cycling: 19 miles (2–3 hours, paved road), Elevation gain/loss: +1,300 / -1,300'; Van transfer: 1 hour
Past landscapes that inspired Renaissance painters
Cycling: 43 miles (5–6 hours, paved road), Elevation gain/loss: +4,329 / -4,329’
Traverse the Crete Senesi lunar-like landscape.
Cycling: 37 miles (4–5 hours, paved road), Elevation gain/loss: +3,491 / -3,392'
Arrive in Chianti, famed for its wine.
Cycling: 43 miles (5–6 hours, paved road), Elevation gain/loss: +3,804 / -3,631'
Marvel at San Gimignano’s Medieval Towers.
Cycling: 36 miles (4–5 hours, paved road), Elevation gain/loss: +2,898 / -3,765'; Van transfer: 1.5 hours
Pedal hills blanketed with vineyards and forests to Siena.
Cycling: 34 miles (4–5 hours, paved road), Elevation gain/loss: +2,616 / -3,642'
Relais Il chiostro di PienzaIl Chiostro di Pienza is housed in a 15th C convent and sits protected and quiet right in the center of this tiny town. It has been renovated but all the beamed ceilings frescoed walls and ancient tile floors have been preserved, nice garden overlooking val d’Orcia with pool.
Castello di GargonzaCastello di Gargonza is a thirteenth- century fortified village. Enclosed inside the medieval walls, the careful restored houses have retained the simplicity of rural life.Forest trails, relax in the Limonaia garden, sit at our bar with view of medieval tower and the woods surrounding the village
Palazzo Squrcialupi - CastellinaPalazzo Squarcialupi is part of the history of Castellina in Chianti. It is situated in the historical town center, on a road running along the XV century City Wall. Set in the spacious garden, in a most suggestive position, is the swimming-pool. The palazzo has medieval origins and it has been renewed becoming a luxury palace
Cost: Euro 2,450 per person in double occupancy
single room supplement euro 450
Five nights in superior hotels with private bath and breakfast
Four dinners, three lunches & two wine tastings
Snacks and drinks along the way
All maps, trip notes and detailed route directions
GPS: offline maps, and voice navigation with ridewithgps app
All Shuttles and technical assistance
Van Support, all baggage transfers
Experienced English speaking guides
Bike Rental per entire tour
Cicloposse water bottle
Airfare to Italy, train to Chiusi, 2 lunches, 1 dinner, beverages, gratuities, travel insurance, laundry expenses and items of a personal nature.