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Cycling Under the Tuscan Sun Day One: Montepulciano Welcome to blissful Tuscany. From the Chiusi train station your guides will take you to Montefollonico and toast your arrival with a traditional Prosecco during your bike fitting, safety talk and map review. Our first outing will be a ride to the distinctive church of San Biagio on the outskirts of Montepulciano, home of the Vino Nobile – famed as “the king of wines” since the 8th century. Returning to Montefollonico, we’ll enjoy a truly authentic tasting at the Cantine Innocenti with owner and philosopher, Vittorio. We’ll then have a marvelous Tuscan evening with our friends Dania and Umberto, the owners of the luxurious villa La Chiusa. Dania runs the kitchen, and Umberto will be eager to welcome you as a friend, and show you how to live like a local. Savor the region's gourmet specialties, grown on La Chiusa’s estate, then unwind and let this heavenly Tuscan experience take over.
Meal: Dinner Destinations visited: Montefollonico & Montepulciano Distance cycled: 23.2 km / 14.50 miles
Tuscany Bike Tour Photo: Day 1 view from your villa in Montefollonico Day Two: Pienza Embark on a loop ride to Pienza, an architectural gem designed to be the ideal medieval town, and often described as the most beautiful village in Tuscany. In Pienza you will have time to meander the cobbled streets, practice your language skills at a local café, people watch, shop for authentic terracotta ceramics, and taste the local wine-soaked or truffle-dusted pecorino. After lunch, we’ll head through St. Anna Caprena and Petroio; you'll feel like you are riding through a movie set as you cycle through rustic villages on cypress-lined roads. Back in Montefollonico, we’ll dine at the warm, rustic Botte Piena.
Meals: Breakfast/ Dinner Destinations visited: Montefollonico, Pienza, St. Anna in Camprena & Petroio Distance cycled: 37 km/ 23 miles
Tuscany Bike Tour Photo: Day 2 ride to Pienza past the cypress trees Day Three: Montefollonico - Montalcino Today it’s off to the land of the Brunello wines, renowned by some as the world’s finest. The cycling route is challenging, but one of the most beautiful rides in Tuscany. This breathtaking part of the tour includes an unforgettable 10 km downhill ride on the shoulder of Monte Amiata, the highest peak in Tuscany. We’ll pass through Pienza, Bagno Vignoni and Castiglione d’ Orcia, then stop for a delicious lunch at a local osteria in St. Antimo. In the late afternoon, enjoy free time to roam the narrow streets of Montalcino, a picturesque town famous not only for Brunello wines, gourmet honey and pecorino, but for outstanding medieval architecture. We’ll have an evening tasting at the fortress in town followed by another exquisite Tuscan dinner.
Meals: Breakfast/ Dinner Destinations visited: Montefollonico, Pienza, Bagno Vignoni, Castiglione D’Orcia, St. Antimo Abbey & Montalcino. Distance cycled: 55.7 km/ 34 miles
Tuscany Bike Tour Photo: Day 3 ride with views of ancient village Montalcino Day Four: Montalcino - Siena Explore the historic roads of Montalcino before another gorgeous day of cycling through Tuscan countryside. We’ll spin to the 14th century Abbey of Monte Oliveto Maggiore, home to some of the most outstanding Renaissance frescoes. After a gourmet Tuscan picnic prepared by your guides, we will ride through Asciano and Vescona to Taverne d’Arbia, where we will park our bikes and take a van ride to Siena - a medieval city with beautifully preserved Gothic architecture. The city is built around the Piazza del Campo, known by many as the most beautiful piazza in all of Italy. Here you’ll have time to shop while exploring the many hidden medieval walkways; the night is yours to choose a local trattoria for dinner.
Meals: Breakfast/ Gourmet Picnic Destinations visited: Abbey of Monte Oliveto di Maggiore, Asciano, Vescona, Taverne D’Arbia Distance cycled: 52.5 km/ 32.50 miles
Tuscany Bike Tour Photo: Day 4 ride past our friend Enzo working on his olive grove
Day Five: Siena – Radda in Chianti We will return to our bikes in Taverne d’Arbia, then ride deep into the hills of Chianti. Past rows of olive and cypress trees, we’ll arrive Castello di Broglio, where we’ll stop for a tasting at its winery. We’ll continue cycling, fully immersed in vast stretches of vineyards and winding panoramic roads, to Radda for lunch at a local restaurant. Our next stop will be the stunning Borgo di Vescine – a serene 13th century hamlet - for a wine tasting with a local sommelier. Tonight’s dinner will be another authentic feast in town.
Meals: Breakfast/ Lunch/ Dinner Destinations visited: Taverne D’Arbia, Castello di Brolio & Radda in Chianti Distance cycled: 40.5 km/ 25 miles
Tuscany Bike Tour Photo: Day 5 ride to Radda stopping to taste at the Castello Bossi Day Six: Radda – San Gimignano - Florence Shuttle through the stunning hills of Radda to visit San Gimignano, a bustling Tuscan destinations spot, before continuing to Florence where we will end our tour at the train station.
Meal: Breakfast Destination visited: Radda, San Gimignano, Florence Accomplished: Total Satisfaction
TRIP TOTAL: 208.9 KM/ 129 MILES, averaging 40-50 km/ 25-30 miles per day. Optional longer rides available each day.
Tuscany is hilly. On this bike trip you will experience strenuous riding days. A comforting part of this trip is the van. We make it very clear that as our guest you should never hesitate to use the van when the cycling is no longer pleasant for you.
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