Total tour distance: 299 miles
Daily tour distance: 50 miles
Difficulty: 80 / 100
Tuscany is an iconic name, symbolizing the good life - a vacation to enjoy all that is good: food, sun, lifestyle, wine, amusement, and relaxation. The culture of the region adds charm, and you can indulge yourself in this opulent way because you will cycle the famous undulating countryside. This Tuscany cycling tour starts in Pienza, and makes its way to Florence, where along the way you will visit the villages that have made Tuscany famous. You can enjoy very charming 3/4 star accommodations and devour your choice of divine Mediterranean cuisine. The hilly terrain makes this tour somewhat challenging!
Day 1 l Arrival in Pienza
We'll meet you in Pienza, the purest Renaissance town in the world (you will arrive by the train to Chiusi-Chianciano station, a major stop on all the Rome-Florence lines). Fitting of bikes. Lodging at hotel Relais Il Chiostro, a hotel housed in a 15th-century convent in a quiet, secluded location right in the center of Pienza - itself is a rare masterpiece: entirely rebuilt between 1459 and 1462, it was the brainstorm of Pope Pius II. Dinner on your own.
Day 2 l Loop ride to Montepulciano & Nobile Wine (105km)
Your tour starts with a circular ride from Pienza. Be sure to stop along the way to visit the remote convent where parts of The English Patient were filmed, and in the enchanting little hamlet of Castelmuzio. You'll come to Montepulciano, the jewel of southern Tuscany. After relaxing a while, continue your loop up and down with a stop in the village of Monticchiello, the quintessential Tuscan hill town. Now a long easy part wait for you crossing the valley – Val d’Orcia – and warm up enough to face the climb to reach Radicofani, a medieval and enchanting village with a 1200 dating Rocca. After a stroll around the stately old town, we'll head back into the country, along some of those winding cypress-lined roads and stop in another medieval village Contignano. Lodging at hotel Relais Il Chiostro di Pienza.
Day 3 l Ride to Montalcino (75km)
Ride from Pienza to Montalcino, with a pause in fairy-tale Bagno Vignoni, a miniature spa that is among the most unique towns in Europe. Next village Bagni San Filippo and big climb wait for you! You can have lunch in Castiglione d'Orcia, then push on to the monastery of Sant'Antimo, where you might catch one of several vesper services performed each day by the monks. The famed wine town of Montalcino is your destination. Visit the fortress to see a breathtaking view of the entire valley you've just biked, then reward yourself with dinner at our favorite wine cellar.
Day 4 l Ride to Siena (95km)
Ride from Montalcino to Siena. On the way you'll coast along the forested crest of a ridge, home to the famed Monte Oliveto Maggiore monastery. Stop here to visit the beautiful buildings and perhaps have lunch at the restaurant. Afterwards, you'll travel through the fascinating area called Le Crete, Tuscany's answer to the Badlands You will visit the medieval village of Montisi an ancient borgo, natural bridge between the "Crete Senesi" and San Giovanni d’Asso, famous worldwide for its valuable white truffle, rich with farms, hamlets and castles, which are reminiscent of the colors of the paintings of the Renaissance.
Day 5 l Ride the Chianti Hills (90km)
Ride from Siena to Castellina in chianbti Along the way you can visit Castelnuovo Berardenga, a medieval town that marks the gateway to Chianti country. Not far away is Castello di Brolio, a castle that you can visit. There's also the chance to shop at a first-class ceramics workshop just before Radda in Chianti. stop in Radda and continue to Castellina. Lodging at Colle Estrusco Salivolpi in Castellina. Level: challenging Castello di Brolio, Radda in Chianti Gaiole in Chianti
Day 6 l Ride to Greve in Chianti (85km)
Circular bike ride to San Donato, Greve in Chianti. Have a stop at Greve's main piazza, characterized by an original formation of irregular triangular shape, defined by beautiful long porticos. Climb to Panzano with preserved the old walls, gate and the keep of the medieval castle. Last village you visit is Monteriggioni, an impressive city with fourteen turrets crowning a circular surrounding wall. Long but gentle uphill back to Castellina via Lornano and Fonterutoli.
Day 7 l Departure day (optional short ride: 32km)
Short optional ride of 32km if desired, or departure after breakfast. Taxi to Chiusi or Siena on your own.
- Deluxe lodging 3 and 4 stars - double room with private bath
- Buffet breakfast daily
- All luggage transfers from hotel to hotel
- Local emergency support throughout your tour during daylight riding hours
- Arrival orientation and bike set up
- Route maps, route cue sheets with suggestions for visitation and site information
- All pre and post travel planning services
- A package of pre-travel documents sent electronically to help you prepare for your trip.
Stay in charming 3 & 4-star hotels in convenient locations. All lodging includes private bathroom and a variety of other amenities. Hotels included:
- Relais Il Chiostro
- Hotel Giglio
- Relais Chiostro de Carmine
- Palazzo Squarcialupi
Optional: Road bikes and upgraded hotels available. Please inquire.