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Short Escape Tuscany Wine Tour

Short Escape Tuscany Wine Tour, a luxury, self guided bike tour


Our Beautiful Tuscany Wine Country Bike Tour offers a sunny Mediterranean ambiance and a spirited flair for hospitality. Tuscany nourishes the soul and leads you to rejoice in the earthly pleasures of daily life!

Self Guided Tour, 5 Days/ 4 Nights

Explore Tuscany Wine Country on this short escape. This is a shorter (5 day/4 night) version on our most popular Tuscany Biking trip – offering 3 full days of cycling and 2 half days. So saddle up for a great trip in Tuscan Wine Country…
Tour Departures: Any date between 15th March to end of October

Pienza ~ Montalcino ~ Chianti

Definitely our best selling bike tour in Italy, this memorable cycling tour lets you experience the region’s world famous wine culture. Bike along tranquil country lanes, tracing the expanses between farmland crowned with walled villages, ancient monasteries in secluded valleys and medieval forts. Staying in Pienza, Montalcino, Siena and heart of Chianti, you are sure to experience the true essence of Tuscany, where history, beauty and, of course, wine abound.

Day 1: Pienza
Meet & Greet in Pienza, widely known as the “ideal city of the Renaissance”  for your welcome, orientation and bike fitting. Pienza exemplifies Take a stroll through the beautiful cobblestone streets ~ the town streets are full of small charming shops selling typical local products, such as fine wines, pecorino, spices, pici (handmade pasta) and so on. We recommend stopping and tasting! Optional test ride to San Quirico d’Orcia.   Distance 20km /12.5 miles.

Day 2: Montepulciano & Vino Nobile
Today’s bike ride takes you on a looped ride to Castelmuzio, Montichiello and Montepulciano ~ the jewel of Southern Tuscany.  Stop along the way to visit the convent where parts of The English Patient were filmed, and in the enchanting hamlet of Castelmuzio. Arrive in Montepulciano for lunch before returning to Pienza with a stop in the village of Monticchiello. Distance 55km/34 miles.

Day 3: Montalcino Brunello Country
Ride from Pienza to Montalcino, with a pause in the fairy-tale like Bagno Vignoni, a miniature spa town. Lunch in Castiglione d’Orcia, then push on to the monastery of Sant’Antimo before heading on to your destination Montalcino, a town renowned for its wine. Visit the 14th century fortress to see a breathtaking view of the entire valley you’ve just biked. Distance 46 km/ 28,5 miles

Day 4: Siena
Today you start your bike ride with a 10 km descent and pass through Buonconvento, heading northbound to Siena. In Murlo visit a fascinating Etruscan Museum. Continue to Ville di Corsano, end up at the arch gate San Marco. You’ll have time to take a leisurely stroll around this art city and explore the wonderful Torre del Mangia, Duomo and Piazza del Campo. Option A: 60 km/37.5miles – Option B: 52 km/31 miles

Day 4: Chianti Hills
End of bike tour – optional bike ride in chianti to Castello di Brolio, a beautiful bike ride on Chiantigiana road. Distance 50 km /31 miles

What’s Included?

Four nights in excellent three-star superior hotels
Four breakfasts
Route notes, maps, elevation gain and city map
Sightseeing, restaurant and shopping suggestions in handbook
All Baggage transfers
Pick-up of bikes and gear in Siena
Sales taxes

Tour Departures: Any date between 15th March to end of October