7-Days / 6-Nights
Double occupancy:
🇨🇦 $4,695 CAD / guest
🇺🇸 approx. $3,410 USD / guest
Single supplement:
$1495 CAD, approx. $1,086 USD
Single supplement bookings: Phone 1 (877) 777-5699
Please CLICK HERE view our tour package
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!
Day One — 17 km / 11 mi (elevation: 265 m)
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.
Day Two — 60 km / 37 mi (elevation: 1,020 m)
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 — 61 km / 38 mi (elevation: 900 m)
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 — 57 km / 35 mi (elevation: 750 m)
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 — 48 km / 30 mi (elevation: 610 m)
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 — 62 km / 39 mi (elevation: 815 m)
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!
*Please note: Itinerary is subject to change to provide our guests with the best tour experience.
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
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Hybrid Bike 🇨🇦 $370/guest
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Carbon Road Bike 🇨🇦 $489/guest
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E-Bike 🇨🇦 $590/guest
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PICK-UP - First day of the tour
DROP- OFF - Last day of the tour
No, there will be time to change before the first bike ride.
Yes – all of our rental bikes come equipped with a rear bag (pannier or trunk bag) or a small bag (Road bike) to carry essentials like snacks, cameras, or extra layers while you ride. Larger luggage will be transported separately by our support van each day.
Our tours run rain or shine! We recommend packing quality rain gear and layers so you can stay comfortable in wet weather. If the conditions become unsafe (such as high winds or lightning), our support van will be available to shuttle you and your bike to the next stop. We always adapt plans to keep everyone safe and comfortable.
Yes! If you’d like to take a break from cycling, you’re welcome to ride in the support van to the next destination. Some guests choose to take a day off to relax and recharge by enjoying the views form the van. You are always able to call it a day cycling or start cycling at any point throughout the ride.
Travel insurance is not included in the tour price. We strongly recommend purchasing your own travel insurance to cover trip cancellations, medical expenses, lost luggage, and any unexpected events before or during the tour.
Yes – we provide GPS routes for every tour. Before your trip, you’ll receive digital route files that can be used on a GPS device or smartphone app.
We recommend bringing one to two carry‑on sized suitcases per person. This helps us fit everyone’s bags comfortably in the support van. Larger items are best left at home, but we can assist with storing any extra luggage that won’t be needed during the tour.
Yes – helmets are provided and must be worn at all times while cycling, as they are mandatory by law and Pedal and Sea Adventures. Guests are also welcome to bring their own helmet if they prefer to use one they’re already comfortable with.
No – gratuities for your guides are not included and are left to your discretion. As a general guideline, we suggest $20–$25 per guest, per day, per guide. Gratuities for meals and lodging are covered, but bar bills and any personal extras are not included.
Yes, give us a call on 902-858-3030 or email us at info@pedalandseaadventures.com
