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Ventimiglia Siena, a breathtakingly beautiful medieval city, has at its  heart a central piazza known as Il Campo. This piazza is known worldwide as the setting for the Palio - a horse race run two times every summer.

Italy Experiences

Beautiful Tuscany

Our Beautiful Tuscany Bike tour is a luxury, guided bike tour


Our Beautiful Tuscany Bike tour is a luxury, guided bike tour that captures the essence of glorious Tuscany and features some of the best scenery in the region. A stylish and unique experience!

Montepulciano ~ Pienza ~ Val d’Orcia
7 Day / 6 Night, Guided Tour

This tour has captured the essence of glorious Tuscany and features some of the best scenery in the region.  Starting at the beautiful Villa Marsili, in Cortona, this tour lets you discover Montepulciano, Pienza and Val d’Orcia through a landscape of sculpted curves created over the centuries by wind, rain, and man. The mystique of this land lies not only in its landscape, but also in its nature, its vineyards and its history: oak woods, olive groves and vineyards overlook enchanting hillsides, medieval villages and historical monuments. Each day you rise, enjoy excellent coffee, cycle for five or six hours in the fresh air and spend the night in a warm, welcoming inn.  The tour ends on a high note in the magnificent city of Siena.

Day 1: Cortona

Nice to meet you! Transfer from Chiusi station to the charming Villa Marsili where your bike fitting and tour introductions  take place. Explore this delightful hill town, made famous by Frances Mayes in her bestselling novel ‘Under the Tuscan Sun’. Stroll through the winding narrow (and steep! ) medieval streets, then enjoy a fabulous welcome dinner at Le Loggette in main square.

Day 2: Lake Trasimeno and Val di Pierle

Your bike tour to Trasimeno lake begins with cycling to Val di Pierle and its splendid castle or “Rocca”. The castle was built prior to the 10th century and belonged to the marquises of Monte Santa Maria Tiberina.  Then enjoy an uphill cycle to the top of Cima di Tuoro from where you will be able to enjoy a stunning view of the Lake and its islands before beginning your welcome descent. Distance 52 km/32.5 miles.

Day 3: Pienza and Montepulciano  

Today you bike to  Montepulciano and explore rolling hills before climbing to Pienza.  Ride from Cortona to Montepulciano, a jewel in southern Tuscany and stop in the village of Monticchiello, the quintessential Tuscan hill town. Bold cypress trees line our route to the Orcia valley where you bike through the fields that inspired Renaissance painters. Distance 50 km/ 31 miles…


Day 4: Val d’Orcia and Radicofani   

Enjoy a loop bike tour in the  Orcia valley and a climb to Radicofani, a medieval and enchanting village with ‘Rocca’ dating to 1200.  Then head downhill to Contignano. On the way back have a “pecorino” –  sheep milk cheese tasting –  at Pianporcino organic farm. Distance 66 km/41 miles.

Day5: Montalcino and Brunello wine

Cycle downhill to the fairy-tale like Bagno Vignoni, a miniature spa and unique town, then push on to the monastery of Sant’Antimo. The famed wine town of Montalcino is a highlight: from its fortress see a breathtaking view of the entire valley you’ve just biked. Once back in the saddle you are on your way to a winery where you will enjoy the local brunello. Distance 45 km/28 miles.

Day 6: Monte Oliveto Abbey & Siena 

Enjoy the downhill ride from Montalcino, stop at Giovanni d’asso, an ancient borgo (burough)  famous worldwide for its valuable white truffle, is rich with farms, hamlets and castles, reminiscent of the colours of the paintings of the Renaissance. Afterwards, you’ll travel through the fascinating area called Le Crete, Tuscany’s answer to the Badlands. Distance 55 km/34 miles.

Day 7: Siena

Arrivederci! Your bike tour has ended – explore Siena on your own before leaving by train for your next destination in Italy.

What’s Included?

6 nights in superior hotels with private bath and breakfast
4 dinners, one lunch & two wine tastings
Snacks and drinks along the way
All maps, trip notes and detailed route directions
All Shuttles and technical assistance
Van Support and all baggage transfer
Experienced guide
Water bottle
Sales taxes

What’s not included?

Not included: Airfare to Italy, train to Chiusi, 5 lunches, 2 dinners, alcoholic/non-alcoholic beverages, gratuities, travel insurance, laundry expenses and items of a personal nature

Dates and Pricing

Price Per Person: Euro € 2,950 (based on double accommodation). Single room supplement € 550 per person.

Bike Rental: 
Touring/hybrid bike Euro 180
High-end race bike: Euro 210
E-bike: Euro 210

DATES 2022:


Helpful Notes


LEVEL: Moderate to Challenge
BEST TIME:from March to October