Italia
Tuscany - Biking Classic
Trip Details
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“Birthplace of the Renaissance, land of Dante’s poetry and Chianti wine, muse to Michelangelo.”
Tuscany is rightly world-renowned for offering all the ingredients of a truly enriching travel experience. Travelling by bicycle allows you to discover the quieter, more authentic side of this region—away from the well-trodden tourist routes and into the very soul of Italy.
Is it one of the most beautiful regions on earth? We certainly think so.
On our Classic trip, we stay in a carefully curated mix of distinctive hotels, charming agriturismi, and comfortable inns. With the exception of Siena, all feature fabulous swimming pools—and every host will welcome you with open arms.
Enjoy!
Highlights
- Small groups and passionate local guides
- A ride you’ll never forget: from Asciano to Pienza, with a picnic en route at a secret spot boasting breathtaking views.
- Carefully selected hotels
- A meal to remember: lunch at Tre Porte in the picture-perfect village of Monticchiello.
- Dine à la carte at hidden local restaurants off the tourist trail
Package Included
- Expert guides throughout the journey
- Support vehicle during the route
- 7 nights accommodation
- Daily breakfasts, 2 lunches and all dinners except one
- Cooking course with guest chef
- Entry to tastings, selected historical sites and museums
- Detailed GPS routes
- Luggage transport
Not included
- Bicycle hire
We’ve included your arrival night in Siena, making this an 8-day trip. If you’d like to add extra nights at the trip hotel, simply indicate this on your registration form. Most guests arrive via Rome—Siena is easily reached by train.
Day 1 · Siena
We’ll meet in Siena and begin the tour with a walking tour led by our favourite local guide. In the evening, enjoy a welcome reception followed by dinner at a traditional trattoria. Buon appetito!
Day 2 - 3 · Castellina in Chianti
We cycle north through rolling fields and vineyards. After lunch in a tiny village, we’ll continue through Radda en route to Castellina. Before dinner at a local trattoria, enjoy an exclusive wine tasting.
On Day 3, take in a scenic ride through the Chianti hills with a stop at the Castle of Meleto, an iconic landmark tied to one of the region’s most historic families.
Our hotel, once a noble palace, is now one of the finest in Chianti.
Day 2 Distance: 46 km; 900 m gain or 75 km; 1335 m gain
Day 3 Distance: 49 km; 860 m gain or 63 km; 1050 m gain*
Day 4 · Sovicille
We begin with a glorious descent into the valley south of Castellina. Today’s highlights include the medieval town of Monteriggioni, famed for its preserved walls and cobbled lanes. Enjoy lunch at a countryside bistro before one final descent to our rural hotel, set among vineyards and complete with a swimming pool.
Distance: 56 km; 700 m gain
Optional Add-on: 39 km; 600 m gain*
Day 5 · Asciano
A gentle descent and rolling hills lead us west to Monteroni d’Arbia for lunch, before continuing to Casabianca, where we’ll stay at a welcoming agriturismo run by a mother and daughter passionate about winemaking.
You may choose to visit the extraordinary Monte Oliveto Maggiore monastery along the way. A local guide will introduce the 16th-century frescoes by Signorelli and Sodoma.
Distance: 55 km; 930 m gain or 78 km; 1370 m gain*
Day 6 -7 · Pienza
We’ve saved the most stunning scenery for last. Ride through the postcard-perfect villages of Petroio and Castelmuzio on your way to Renaissance-rich Pienza.
On the final day, choose between a moderate loop or a longer challenge visiting Montepulciano and Monticchiello—cycling through what can only be described as a photographer’s paradise.
Our hotel sits just 150 metres from Pienza’s central piazza and offers a relaxed atmosphere and spacious rooms.
Our final evening features a celebratory meal, local wines, and a toast to our Tuscan adventure. Viva la dolce vita!
Day 6 Distance: 30 km; 650 m gain or 46 km; 990 m gain
Day 7 Distance: 37 km; 735 m gain or 81 km; 1535 m gain*
Day 8 · Departure
Transfer to Chiusi for trains onward.
*Distance and elevation gains may vary depending on hotels chosen for specific departure.
Hotel Santa Caterina – Siena
This charming hotel occupies an 18th-century villa overlooking the valley just outside Siena’s medieval city gates. The guest rooms are cosy and inviting, with several enjoying panoramic views. A short stroll brings you to a variety of local restaurants and cafés.
Il Colombaio – Castellina in Chianti
Set just outside the heart of Castellina, Il Colombaio is a peaceful retreat with comfortable rooms and a beautiful swimming pool. The location allows for an easy walk into town to explore restaurants and wine bars.
Casale Il Colombaio di Toiano – Sovicille
Dating back to the 14th century, this restored stone farmhouse is now a warm and welcoming country inn. Your hosts, Giuseppina and Paolo, bring the property to life with their hospitality. The comfortable rooms and sublime gardens make for a tranquil countryside stay.
Podere Alberese – Asciano
A recent and much-loved discovery, this family-owned 17th-century property is nestled among vineyards, olive groves, and organic gardens. The family produces excellent wines, and there’s a heated swimming pool to relax in after a day’s ride.
Hotel San Gregorio – Pienza
Just steps from Pienza’s historic centre, this elegant 3-star hotel features spacious suites, each with a sitting room and Jacuzzi bath. A swimming pool and on-site restaurant—added in 2007—enhance the comfort and convenience of your stay in this beautiful Renaissance town.
Pre-trip Extension in Monopoli
US $495
Includes two nights stay at Palazzo Indelli, transfer to hotel on arrival from Bari or Monopoli, 1/2 day walking tour, and transfer to Casale del Murgese for the start of the trip
Post-trip Extension in Lecce
US $595
Includes two nights stay at Risorgimento Resort and 1/2 day walking tour