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. And if that is not enough, we have added three cooking classes to help send you home as World Class Chefs!



  • Tuscany cycling and cooking tour
  • Tuscany cycling and cooking tour
  • Tuscany cycling and cooking tour
  • Tuscany cycling and cooking tour
  • Tuscany cycling and cooking tour
  • Tuscany cycling and cooking tour
  • Tuscany cycling and cooking tour
  • Tuscany cycling and cooking tour
  • Tuscany cycling and cooking tour
  • Tuscany cycling and cooking tour
  • Tuscany cycling and cooking tour
  • Tuscany cycling and cooking tour
  • Tuscany cycling and cooking tour
  • Tuscany cycling and cooking tour
  • Tuscany cycling and cooking tour
  • Tuscany cycling and cooking tour
  • Tuscany cycling and cooking tour
  • Tuscany cycling and cooking tour
  • Tuscany cycling and cooking tour
  • Tuscany cycling and cooking tour
  • cycling tour tuscany
  • tuscany cooking cycling tour
  • Tuscany cycling and cooking tour vegetables
  • Row of cheeses in Tuscany
  • tuscan countryside house with table and chairs

2023 Itinerary

Day One — 28km (elevation: 551 mt)

You will check into your accommodation and then start a short warm-up bike ride. Today's ride is a test ride day as it is just a taste of what is yet to come!. We ride from the villa to San Giovanni D’Asso - famous for the white Truffle. From there we head to Montisi, a very small and pretty medieval village now important for its olive oil. Afterwards we ride back to our Villa through Trequanda. Your accommodation for the entire tour will be Castello delle Serre.


Day Two — 63 km (elevation: 1.154 mt)

Today we will enjoy a nice loop ride and tonight’s first cooking class!  Our first destination is Pienza, followed by a ride to San Giovanni D’Asso and Torrenieri. This is the only flat road for today. From Torrenieri, we cycle to San Quirico on the old Cassia Road and part of Via Francigena.  After a break in the main square in San Quirico, we ride to Pienza. Here you can enjoy the beautiful view of the Val D’orcia valley — a UNESCO World Heritage Site. Also here you can try the best gelato at “Gelateria Buongusto”. The second part of the ride is on a beautiful secondary road until Castelmuzio and Petroio village famous for their olive oil. On the way back we’ll ride very close to Sant’Anna in Camprena, which is famous as the location for the movie: The English Patient


Day Three — 55 km (elevation: 947 mt) 

Today could be a challenging day! We will enjoy a guided city tour of Siena as well as the ride to Siena through a part of the Chianti area. The Chianti area is famous for their red wine and these beautiful vineyards take us all the way to Siena. Siena has one of Europe’s greatest medieval town squares which is linked to the historic Palio — the famous horse races. After visiting Siena, we will drive you back to the villa.


Day Four — 65 km (elevation: 1.069 mt)

Today we will enjoy a bike ride followed by another cooking class. The loop ride today is in the middle of the Crete Senesi land. The fist part of the ride is downhill to Asciano. We ride through this village and immediately we take the road to Lauretana. The first part of this road can be challenging, but the view of the hills is breathtaking. You’ll feel as though you’re on the moon! The second part is considered easy to moderate for our arrival in Rapolano Terme. It is here where we will enjoy lunch after which we will ride back to the villa. 


Day Five — 53 km (elevation: 787 mt)

Today we will ride to Cortona as well as enjoy our third and last cooking class! We start from the villa and climb to Trequanda.  This charmed land of rounded hilltops is covered with vineyards and acres of sunflowers bathed in pastel sunlight. Feeling invigorated, we will set off on a long, slow climb towards Cortona — the delightful hill town made famous by Frances Mayes in her bestselling novel Under the Tuscan Sun. After lunch at a local trattoria, we’ll stroll around Cortona’s pristine medieval street and then we’ll begin our descent back to the villa by van.


Day Six — 61 km (elevation: 1.107 mt)

Our last ride is to Montalcino — the famous village of Brunello wine. Before our arrival in Montalcino, we ride through the little village of Chiusure and abbazia di Monte Oliveto, which is still a functioning monastery founded in 1313 by Bernardo Tolomei. Tolomei was a famous professor of law who later devoted his life to God at the age of 40. After cycling a nice secondary road mostly downhill, we arrive in Buonconvento. From here and after a good coffee, we climb to Montalcino in the middle of the vineyard of San Giovese grapes. The way to go back to the Villa starts with a long decent from Montalcino to Torrenieri, then a flat, nice road to San Giovanni D’Asso. From here we’ll ride UP and DOWN to the Villa.

Day Seven — Farewell

Today is our last chance to savour the scenery together before departing. After breakfast we will drive you back to Siena Station. We're always sad to part, but we know the friendships we make in Tuscany will continue to enrich our lives in the years ahead!


* Details subject to change. 

2023 Availability

  • May 16–22, 2023
  • June 13–19, 2023(FULL*)
  • September 17-September 23
  • September 25–Oct 1, 2023 
  • Custom groups anytime 



  • 6 Nights’ Accommodation
  • Pick-up/Drop-off for Tour
  • 6 Breakfasts, 1 Lunch, 6 Dinners  
  • 3 Custom Italian Cooking Classes
  • Support Vehicle
  • Bilingual Guide
  • Detailed Itinerary & Route Maps
  • Snacks and Refreshments
  • Wine, oil and cheese tastings
  • Trip Support

Reserve Now Back to Guided Tours


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

• $3,995 per person based on double occupancy
• $850 single supplement 
 • Hybrid bicycle rental: $275
• Carbon road bicycle rental: $369
• Kalkhoff E-bike rental: $459


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