Guided
Southern Tuscany Bike Tour
Southern Tuscany looks different from other parts of the region. This area is made up of endless rolling hills covered with grain fields, sunflowers, and vineyards. It is a rich green valley that stretches from the town of Siena south to a mountain called Amiata. Centuries ago Renaissance painters were drawn to these verdant hills. Today the best landscape photographs of Tuscany are taken here. This bike tour starts in the Val d’Orcia, a river valley known for its hill towns, wine, and thermal waters. We spend two nights in Montalcino, a walled town set high on a hill and punctuated with an imposing castle. This town is home to one of Italy’s most prestigious wines, the Brunello di Montalcino. We tour a Brunello winery and learn how Sangiovese grapes are transformed into one of Tuscany's best reds. We soak in the soothing thermal waters of Bagno Vignoni and tour an organic cheese farm. We stay in the perfectly preserved Renaissance town of Pienza. We overnight in Montepulciano, a Renaissance gem built high on a volcanic ridge. The tour concludes in Cortona, a town nestled high on green mountainside above terraced olive groves.
​Highlights​
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Swim at a thermal spa
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12th Century castle visit
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8th Century abbey visit
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Cheese farm visit with lunch
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Winery tour and tasting
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The Tuscan hill towns of Montalcino, Pienza, Montepulciano and Cortona
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Guided wine tasting
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Beautiful vistas of vineyards and olive groves
Price
US$ 2,150 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
7 Days, 6 Nights
Meet / Finish
Florence / Cortona
Route Rating
Moderate: 4-27 miles (6-44 km) per day over hilly terrain. Extra miles available.
Bikes and Gear >
Terms and Conditions >
Daily Itinerary
Day 1 and 2: Montalcino
We meet in Florence and shuttle to Montalcino. A warm-up ride leads to a Brunello winery where we tour and taste. In the evening we dine on traditional Tuscan cuisine at a charming family-run restaurant. On Day 2 we cycle to a country inn for a hands-on lunch cooking class. Later we visit Tuscany’s prettiest Romanesque church and top the day off with a guided wine tasting in a walled castle.
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Day 3: Pienza
The road to Pienza passes through a village called Bagno Vignoni. The hot mineral waters of Bagno Vignoni have been drawing travelers since Roman times. Before lunch we test the curative powers of these natural waters. After lunch it is off to Pienza, an architectural wonder. Pienza was built at the behest of a Pope who razed his hometown to build the perfect Humanist Renaissance town. The buildings, the piazzas, and the streets have been perfectly preserved.
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Day 4: Pienza
We ride to a cheese farm where a Swiss family has been making artisanal sheep cheese, called pecorino, for the last 30 years. We tour their property and see firsthand how Ewe's milk is lovingly transformed into flavorful cheese. We learn about life on a small Tuscan farm with sheep, goats, and pigs. Lunch is a farm to table treat. We dine al fresco and try their homemade cheeses, pastas, breads, and meats. After lunch we backtrack to Pienza in time to enjoy an apertivo while admiring a spectacular sunset.
Day 5: Montepulciano
A rolling back road takes us through a fortified hamlet called Montefollonico. We stop for a refreshments before continuing on to Montepulciano, Tuscany’s highest hill town. Montepulciano is a town of rare beauty full of elegant Renaissance palaces, ancient churches, and charming squares. Its lofty location makes for vast panoramas over the valleys below. Centuries ago wine makers carved cantinas into the soft volcanic stone. To learn more about the local Vino Nobile, we do a winery tour and taste some recent vintages.
Day 6: Cortona
Our last ride takes us through rolling farmland to the ancient town of Cortona. The city, enclosed by stone walls, sits on the top of a hill some 600 meters (2,000 feet) above sea level. This dominant position creates spectacular vistas with views all the way to Trasimeno Lake. Cortona is a mix of medieval, Renaissance and Baroque architecture. The streets are narrow, sometimes steep, which all seem to lead to the main square. Despite the fame it found through the book and movie, Under a Tuscan Sun, Cortona has retained a genuine, untouristy feel.
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Day 7: Shuttle to Florence
Shuttle to Florence where we drop you off at the Florence train station before 12 noon.
Daily Distance
Lodging
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 >
Hotel Corsignano
Pienza (1 night)
The Hotel Corsignano has breathtaking views of the Orcia Valley and offers a terrace with a hot tub. Rooms are quiet, spacious and modern.
Mueble il Riccio
Montepulciano (1 night)
The Mueble Il Riccio is a small family-run inn just steps away from the town's main piazza. The hotel has a roof top terrace with majestic views.
hotel website >
Hotel San Michele
Cortona (1 night)
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 >
What's Included
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All lodging (three and four star hotels)
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All breakfasts
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Two dinners
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One lunch
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One cooking class
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One picnic
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Winery tour
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Cheese farm tour
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Guided wine tasting
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Van transfer from Florence on Day 1
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Van transfer to Florence on Day 7
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Five beautiful rides
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Use of bike of a high-end bike (hybrid, road or e-bike)
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Use of a helmet
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Souvenir water bottle to keep
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Van support
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A friendly bilingual guide
Departure from Cortona, End of Tour
On the last day of the bike tour we will shuttle you from Cortona to Florence. Along the way we will stop for lunch at the Badia a Coltibuono restaurant in Chianti (included in your tour). After lunch we will drop you off at the Florence train station.
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.
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.
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.
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.
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.
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.