Guided
Southern Tuscany Castles Bike Tour
Southern Tuscany has some of the most enchanting landscapes in Italy. Picturesque hill towns are surrounded by verdant rolling hills, fertile vineyards, and ancient olive groves. This region produces robust red wines and smooth creamy cheeses. This tour shows you the best of Southern Tuscany. We stay in the picture-perfect hill towns of Cortona, Pienza, and Montepulciano. We visit Medieval castles, a thermal bath, and an organic cheese farm. Stunning rides during the day are followed by sumptuous Tuscan dinners at night. Riding distances are flexible. Van support is there so you can ride a lot or a little, it is up to you.
​Highlights
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Banfi winery visit and tasting
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Hot springs pool visit
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Organic cheese farm visit and tasting
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Castle visits (Radicofani and Montalcino)
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Overnights in the hill towns of Cortona, Pienza, and Montalcino
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Spectacular wine country rides
Price
US$ 1,900 per person, double occupancy
Dates
Email us your dates. We can schedule the tour when you want.
Single Supplement
+ US$ 400 for single room occupancy
Length
8 Days, 7 Nights
Meet / Finish
Cortona / Siena
Route Rating
Moderate: 16-40 miles (25-64 km) per day over hilly terrain. Extra miles available.
Bikes and Gear >
Terms and Conditions >
Day 5: Montalcino
A fast downhill takes us to an ancient thermal bath called Bagno Vignoni. Swim or soak in the thermal waters before enjoying a group lunch in a small trattoria. After lunch we roll through a walled village with a lovely rose garden. The road climbs steeply through pristine vineyards before arriving in Montalcino. Our hotel has panoramic rooms overlooking a panoramic pool. Montalcino is known for a red wine called Brunello. This dense, robust red is among the most prestigious wines in the world. Before dinner we visit the Montalcino castle and learn about the local wines during a guided wine tasting.
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Day 6: Montalcino
We roll through Brunello vineyards on our way to a secluded abbey. The 12th Century Sant’Antimo Abbey is Tuscany’s most beautiful Romanesque church. Heading further south we cycle to the Banfi estate and winery. We tour the winery, sample their most prestigious vintages, and have a group lunch at their restaurant. A long uphill takes us back to Montalcino.
Day 7: Castelnuovo Berardenga
We ride through a wide-open landscape. Quintessential Tuscan farmhouses and cypress lined lanes embellish a rolling countryside. This is the road you see in many Tuscan postcards. Along the way we stop at a hillside monastery and tour its frescoed cloister. Our ride ends at a country inn located in a small 16th century village. We celebrate our weeklong adventure with a group dinner.
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Day 8: Shuttle to Siena
After breakfast we accompany you to the Siena train station. The train to Florence takes 1.5 hours while the train to Rome takes 3.5 hours.
Day 1: Cortona
We rendezvous at our hotel in Cortona. Cortona can easily be reached by direct trains from Florence (1.5 hours) and from Rome (2 hours). We have lunch, get fitted on the bikes and do a warm up ride. Group dinner in a small ristorante.
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Day 2: Cortona
A short ride takes us to Pierle and its crumbling 14th Century castle. Cycling south we crest a ridge with views over Trasimeno Lake. A downhill leads to the lakeside village of Tuoro. We picnic in Tuoro before riding back to Cortona.
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Day 3: Pienza
We ride through open farmland before arriving in the town of Montepulciano. The highest of Tuscany’s hill towns, Montepulicano has a perfectly preserved historic center chock a block full of Renaissance palaces and wineries. Tour a winery to learn more about the local wine called Vino Nobile. We follow quiet backroads on our way to Pienza, a utopian Renaissance town. In the 15th Century a Pope transformed his hometown into this architectural wonder. Our hotel is located in a 15th Century monastery in the center of town.
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Day 4: Pienza
A country road through a sun-drenched valley leads to a fairy tale castle. You can climb the tower of the Radicofani castle for breathtaking views. We have a group lunch in the shadow of the castle walls. On the way back to Pienza we stop at an organic cheese farm where we see how fresh ewe’s milk is transformed into aromatic Tuscan cheese.
Daily Itinerary
Daily Distance
Hotel San Michele
Cortona (2 nights)
The Hotel San Michele is located in a 15th Century mansion in the center of Cortona. The building has been completely renovated, but retains its Renaissance charm.
hotel website >
Hotel Corsignano
Pienza (2 nights)
The Hotel Corsignano has breathtaking views of the Orcia Valley and offers a terrace with a hot tub. Rooms are quiet, spacious and modern.
Hotel Dei Capitani
Montalcino (2 nights)
Situated in the historical center of Montalcino, this 18th Century building has a panoramic pool. Rooms are air-conditioned and offer breathtaking views.
hotel website >
Lodging
Siena Hotel Supplement During Palio
During the Palio (Siena's horse race) hotel prices triple. A surcharge of US$ 100 per person will apply for if you stay in Siena Jun 29-30, Jul 1-2, or Aug 13-16.
What if it Rains?
On self-guided tours there is no van support. But, we do move your luggage. If it rains you can catch a ride with us when we move your bags, just call to make arrangements.
What if it Rains?
On self-guided tours there is no van support. But, we do move your luggage. If it rains you can catch a ride with us when we move your bags, just call to make arrangements.
What if it Rains?
On self-guided tours there is no van support. But, we do move your luggage. If it rains you can catch a ride with us when we move your bags, just call to make arrangements.
Siena Hotel Supplement During Palio
During the Palio (Siena's horse race) hotel prices triple. A surcharge of US$ 100 per person will apply for if you stay in Siena Jun 29-30, Jul 1-2, or Aug 13-16.
What if it Rains?
On self-guided tours there is no van support. But, we do move your luggage. If it rains you can catch a ride with us when we move your bags, just call to make arrangements.
Siena Hotel Supplement During Palio
During the Palio (Siena's horse race) hotel prices triple. A surcharge of US$ 100 per person will apply for if you stay in Siena Jun 29-30, Jul 1-2, or Aug 13-16.
What if it Rains?
On self-guided tours there is no van support. But, we do move your luggage. If it rains you can catch a ride with us when we move your bags, just call to make arrangements.
Siena Hotel Supplement During Palio
During the Palio (Siena's horse race) hotel prices triple. A surcharge of US$ 100 per person will apply for if you stay in Siena Jun 29-30, Jul 1-2, or Aug 13-16.
Villa Curina Resort
Castel. Berardenga (1 night)
Surrounded by rolling Chianti hills, the Villa Curina Resort is located in a 16th Century village. The hotel has a large garden and swimming pool.
hotel website >
What's Included
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All lodging (four and five star hotels)
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All breakfasts
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Two dinners
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Two lunches
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One picnic
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Organic cheese farm visit and tasting
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Hot springs pool
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Brunello winery tour with tasting
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Montalcino castle visit with wine tasting
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Radicofani castle visit
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Seven beautiful rides in Tuscan countryside
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Use of a high end bike (hybrid, road or e-bike)
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Van support
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Friendly bilingual guide
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Private van transfer to Siena at tour’s end
Departure from Siena, End of Tour
The bike tour ends at a hotel just outside of Siena. On the last day we will shuttle you to the Siena train station for easy connections to Florence or Rome.
Want to Save?
Consider one of our self-guided bike trips. We can schedule a self-guided bike tour whenever you want March 1 to October 31.
Our Dates Dont Work?
We may be able to offer the dates you want. Email us with the dates you prefer.