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Self-Guided
Southern Tuscany Bike Tour
Most Tuscany bike tours visit the northern part of the region including Florence, Chianti, and Siena. Fewer trips venture off the beaten path exploring southern Tuscany. Equally beautiful, but less touristy, southern Tuscany is known for its sun-drenched farmlands, picture perfect hill towns, and exceptional red wines. Spend seven days cycling through beautiful hill towns including Montalcino, Pienza, and Cortona. Explore a 14th century castle. Tour a winery and sample their Brunello wine. Soak in hot thermal waters at a Roman spa. Learn how full cream sheep's milk is transformed into pecorino cheese during a cheese farm visit. Feast on local specialties including pici pasta (a thick spaghetti), wild boar, and local cheeses. You will be enchanted by the warm people, quiet villages and natural splendor.
​Highlights
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Winery tour with wine tasting
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Swim at a thermal spa
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Cheese farm visit
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12th century castle visit
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8th century abbey
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The Tuscan hill towns of Montalcino, Pienza, Montepulciano and Cortona
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Beautiful vistas of vineyards and olive groves
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Peaceful country back roads
Price
US$ 1,600 per person, double occupancy
Dates
Any date, Mar 1 to Dec 1
Single Supplement
+ US$ 300 for single room occupancy
Length
7 Days, 6 Nights
Meet / Finish
Florence / Cortona
Route Rating
Moderate: 8-27 miles (13-44 km) per day over hilly terrain. Extra miles available.
Bikes and Gear >
Terms and Conditions >
Daily Itinerary
Day 1: Buonconvento
We meet in Florence and shuttle to Buonconvento. You have lunch in Buonconvento with your tour coordinator who reviews the tour and provides route notes and maps. Cycle to Monte Oliveto Maggiore a stunning abbey perched on top of a cliff.
Day 2 - 3: Montalcino
Ride to the perfectly preserved medieval village of Sant'Angelo in Colle. Visit Tuscany's most beautiful Romanesque church. Enjoy a winery tour and learn how sangiovese grapes are transformed into the sublime Brunello wine.
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Day 4: Pienza
Pedal at your own pace to Pienza, built by a Pope to represent the perfect Renaissance city. Swim or soak in the geo-thermal waters of Bagno Vignoni. Tiny Bagnoni Vignoni has been soothing weary travelers since the Romans consecrated the waters to the Nymphs.
Day 5: Montepulciano
See how ewe's milk is turned into pecorino cheese during a cheese farm tour. Zig-zag through the stone streets of Montichiello, a tiny village with great views. Cycle to Montepulciano, a town known for its ruby-red wine called Vino Nobile. Tour the cavernous cellars of an ancient winery.
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Day 6 and 7: Cortona
Bike to the town made famous by the book and movie titled, Under the Tuscan Sun. Nestled high on a hill, Cortona is a delightful village with a medieval air. The bike tour ends in Cortona where frequent trains make for an easy departure on day seven.
Daily Distance
Lodging
Hotel Ghibellino
Buonconvento (1 night)
The Ghibellino is a small modern hotel located on the edge of the historic center of Buonconvento. Rooms are modern, quiet, and air-conditioned.
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 Corsignano has breathtaking views of the Orcia Valley and offers a terrace with a hot tub. Rooms are 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 >
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All lodging (three and four star hotels)
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All breakfasts
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Lunch on Day 1 with the tour coordinator
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Lunch on Day 6 at the cheese farm
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Winery visit and wine tasting
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Luggage transfer from hotel to hotel
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Private van transfer from Florence on Day 1
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6 beautiful rides (extra miles available)
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Use of a high-end bicycle (hybrid, road bike or e-bike)
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Use of a helmet
What's Included
Departure from Cortona, End of Tour
The bike tour ends in the town of Cortona. Frequent trains make for easy departures. It is a 2.5-hour train ride to Rome and a 1.5-hour train ride to Florence. We will be happy to assist you with your post-tour travel plans.
Use our Bike Bags (Panniers) and Save
Save US$ 150 per person. Pack what you need in our bike bags (panniers) and leave the rest of your luggage with us. We will deliver your remaining luggage to the last hotel.
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.
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.
Use our Bike Bags (Panniers) and Save
Save US$ 50 per person. Pack what you need in our bike bags (panniers) and leave the rest of your luggage with us. We will deliver your remaining luggage to the last hotel.
Can I really start any date I want?
Yes! You can start your tour any day of the week, March 1 through December 1. We have complete flexibility with the starting dates.
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.