Italy’s Tuscany region by bicycle


Tuscany, like a fine wine, has been some time in the making. Just the mention of the region conjures images of superb Renaissance art and landscapes famous for rolling hills, olive groves and cypress trees. The many pleasures of Tuscany include tasting wine in Chianti and relaxing in the piazzas of medieval towns. Whatever you do, the combination of great art, sumptuous countryside and memorable food and wine makes a cycling trip to this enchanting part of Italy unforgettable.



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  • Tuscany Italy bicycle tour
  • Tuscany Italy bicycle tour
  • Tuscany Italy bicycle tour
  • Tuscany Italy bicycle tour
  • Tuscany Italy bicycle tour

2017 Itinerary

For a truly unique vacation, let Pedal & Sea Adventures introduce you to a world of history, beauty and amazing culinary riches during our bicycle tour of Tuscany. You will pass through the charming towns of Pienza, Greve, San Gimignano, Siena and Montalcino — to name just a few. Our itinerary provides ample opportunity to explore these incredible places, and to taste food and wine so savoury and fresh that it will be hard not to return for mpre.


Day One — 10-20 km (easy; 1.6 km = 1 mile)

We’ll meet you early afternoon at the train station in Chiusi and shuttle you to our first night’s lodging, Hotel il Chiostro di Pienza, the starting point of your unforgettable adventure. Once you’re settled in your roos, you’ll have your bicycle adjusted and then you’re off for a short warmup ride. Pienza was believed to be the perfect Renaissance city when it was created in 1459 so we have decided to stay here for the first three nights of your tour. Lodging: Hotel il Chistro di Pienza.


Day Two — 70 km (easy to moderate)

You will start the day with a wonderful downhill ride through amazing countryside en route to Radicofani, which dates back 1,000 years. It houses one of the most impressive fortresses in all of Tuscany. After a stroll around this hilltop town, it is back on the bikes to cycle by cypress-lined roadways with a stop at a pecorino cheese factory for a tour and light lunch. After the tour, you will finish the day with a climb back up to Pienza. Lodging: Hotel il Chiostro di Pienza.


Day Three — 55 km (moderate to sometimes challenging)

After another hearty breakfast, you will head out on a loop ride to Montepulciano, best known for its Vino Nobile red wine. But before reaching our destination, we will stop at the Sant’Anna Camprena monastery, well known for the room with the frescoes by Sodoma and where the movie The English Patient was filmed. After lunch it is off to the lovely village of Monticchiello, characterized by a mighty guarded wall that encloses the entire village, before arriving back in Pienza. Lodging: Hotel il Chiostro di Pienza.


Day Four — 46 km (moderate to sometimes challenging)

Today’s bicycle ride takes us from Pienza to Montalcino, via Bagno Vignoni, Castiglion dOrcia and SantAntimo, where mass is still conducted via Gregorian chant. This abbey is one of the most precious remains of Romanesque architecture in Italy. According to legend, SantAntimo was founded by Charlemagne at the end of the 8th century. After visiting the abbey and a light lunch, it is off to Montalcino through a sea of vineyards where San Giovese grapes are grown for the famous Brunello di Montalcino red wine. We will have a chance to taste Brunellos at the vineyard Le Ragnaie before dinner. Lodging: Hotel Vecchia Oliviera.


Day Five — 60 km (moderate)

We leave Montalcino en route to Siena, via Buonconvento, Monte Oliveto abbey, Asciano and the Le Crete area. Still a functioning monastery, Monte Oliveto Maggiore was founded in 1313 by Bernardo Tolomei, a famous professor of law who later devoted his life to God at the age of 40. After, the ride continues to the town of Asciano down its main street past a number of churches before you finish the day in the Gothic city of Siena. Lodging: Hotel Palazzo Ravizza.


Day Six — 50 km (moderate)

From Siena, your ride today will take you through the Chianti red wine countryside to Castellina via San Felice, Castello di Brolio and Radda following the Via Chiantigiana. To this day, Castellina is still a very active village with locals and tourists mingling in the small narrow streets. Before dinner you will enjoy another wine tasting at Casa Emma where varieties such as Merlot are grown but the fields are mostly covered with Sangiovese grape. Lodging: Hotel Palazzo Squarciualupi.


Day Seven — 58 km (moderate to sometimes challenging) 

Leaving Castellina you will cycle past Monteriggioni, literally a town in a castle, as you make your way to San Gimignano. The castle is barely 200 meters across and its 80 residents all reside within the picture-perfect round turreted walls. More vineyards await us today but you will be amazed at how different they look once you get in to the district of San Gimignano. Also known as the City of Towers, it was ounded around the 8th century and at one time home to more than 15,000 people. After visiting the town, you will be driven back to Castellina. Lodging: Hotel Palazzo Squarciualupi.


Day Eight — Farewell

Today is our last chance to savour the scenery together before departing. We hope you enjoy your time and cherish the memories.


* Details subject to change. 

2017 Availability

  • May 13-20 (full)

  • June 10-17

  • September 16-23

  • Custom groups anytime 




  • 7 nights’ accomodation
  • 6 dinners, 1 lunch, 7 breakfasts  

  • Van support, guides, snacks and refreshments

  • Wine, oil and cheese tastings

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All prices in CAD. Click here for a currency converter.  

  • $3,395 per person based on double occupancy

  • $800 single supplement 

  • Hybrid bicycle rental: $249

  • Carbon road bicycle rental: $349

  • Kalkhoff E-bike rental: $369



For returning customers

  • Is this your second Pedal & Sea Adventures tour? Let us know, and we’ll knock $100 off the price.
  • If this is your third Pedal & Sea tour, we’ll take $100 off the price and send you a free jersey.
  • Your fourth Pedal & Sea Adventures tour? We will take $100 off the price, send you a free jersey and give you a complimentary bicycle rental. 

To take advantage of these great incentives, please let our staff know when you book!

Our bikes in Italy


kalkhoff e bike


E-Bike - Kalkhoff

- Model: Agattu Impulse 8R HS

- Top notch drive

- 2.0 motor with sift-sensor

205 km range

- Tire size: 700 X 35



Trek road bike


Road Bike - Trek

- Model: Emonda S 6

- Ultralight carbon frame

- Shimano / Ultegra components

- 22 speed (compact drivetrain)

- Tire size: 700 X 23 or 25 




Trek hybrid bike


Hybrid Bike - Trek

- Model: 7.3 fx

- Aluminum frame

- Shimano components

-27 speed

- Tire size: 700 X 32


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