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Europe
Italy

Tuscany

A cycling vacation through rolling valleys and culinary delights
Guided tour
Our Guided Tour package is our all-inclusive option. You choose your destination, and we take care of the rest! Itineraries, accommodations, meals, and roadside support—everything is planned out, so all you have to do is ride. Best of all, you can ride at your own pace and set off whenever you like. Our guide is there for you throughout the trip and will ensure that your days on the bike go perfectly.
Flight included

Starting at

6399$

per person

Duration

15 days

14 nights

Level

Level:

4 - Advanced - hilly and mountainous - 50 to 90 km

Dates and prices

Date*
Duration
Prices starting at
Note
Date*
September 11–26, 2026
Duration
15 days / 14 nights
Price starting at:
$6,399 per person
Guaranteed departure
( * Please contact us to check availability. )

The life of your dreams

Tuscany is a dream destination! Life is good in this Italian region, where every mile you travel reveals a hamlet even older and more picturesque than the last, and every turn of the road unveils a postcard-perfect landscape. Amid vineyards, villages, and valleys, you’ll discover Tuscany from the vantage point of its charming hilltop villages, allowing you to fully immerse yourself in its simple yet flavorful cuisine that showcases the quality of local ingredients.

From Montepulciano to San Vincenzo, via Siena and the Island of Elba, art and history come together wherever you look. And what better way to explore them than on two wheels!

Package includes

air travel for the passenger, their luggage, and their bicycle with Air Transat;

transportation between the airport and the hotel at the destination, both on the way there and on the way back;

the bus transfer scheduled for Day 14;

14 nights in a three- or four-star hotel, based on double occupancy;

14 breakfasts and 3 dinners;

  • Transportation of luggage between each stopover (one bag per person, maximum 20 kg) as well as transportation of the bike box;
  • The guide will map out the route and update the GPX data via Ride with GPS before the group sets off;
  • Supervision of a VQV guide;
  • Mechanical breakdown assistance and access to a replacement vehicle;
  • Sharing of GPX or Ride with GPS data, maps, and daily itineraries in electronic format 24 or 48 hours before departure;
  • Taxes;
  • Coverage under the Travel Agent Customer Compensation Fund (FICAV), which amounts to $1 per $1,000, as well as the applicable discount.

 

Package includes

air travel for the passenger, their luggage, and their bicycle with Air Transat;

transportation between the airport and the hotel at the destination, both on the way there and on the way back;

the bus transfer scheduled for Day 14;

14 nights in a three- or four-star hotel, based on double occupancy;

14 breakfasts and 3 dinners;

  • Transportation of luggage between each stopover (one bag per person, maximum 20 kg) as well as transportation of the bike box;
  • The guide will map out the route and update the GPX data via Ride with GPS before the group sets off;
  • Supervision of a VQV guide;
  • Mechanical breakdown assistance and access to a replacement vehicle;
  • Sharing of GPX or Ride with GPS data, maps, and daily itineraries in electronic format 24 or 48 hours before departure;
  • Taxes;
  • Coverage under the Travel Agent Customer Compensation Fund (FICAV), which amounts to $1 per $1,000, as well as the applicable discount.

 

Package does not include

equipment, such as a bicycle

travel and cancellation insurance

 

 

Package does not include

equipment, such as a bicycle

travel and cancellation insurance

 

 

Additional information

Departure/Return

Montreal-Trudeau/Rome-Fiumicino

Rome-Fiumicino/Montreal-Trudeau

For groups of 12 or more cyclists, accompanied by our guide.

Route difficulty rating: 4
fairly difficult route;
hilly and mountainous;
relatively steep climbs; 50 to 90 km.

Additional information

Departure/Return

Montreal-Trudeau/Rome-Fiumicino

Rome-Fiumicino/Montreal-Trudeau

For groups of 12 or more cyclists, accompanied by our guide.

Route difficulty rating: 4
fairly difficult route;
hilly and mountainous;
relatively steep climbs; 50 to 90 km.

Check the elevation profiles

Check out the elevation changes along this route and plan your upcoming trip with all the information you need. Please note that the elevation changes are provided for informational purposes only and may not always reflect actual conditions on the ground.

Day-by-day cycling itinerary

Short route: 304 km / Long route: 845 km
1

Day 1

Arrival in Rome and transfer to Arezzo (3.5 hours).

2

Day 2

Rest day or loop via Palazzo del Pero, Castaglion Fiorentino, and Rigutino. Alternative route via Alpe di Poti, Passo di Monte Dogana, Santa Cristina, and Colle Secco (46–72 km).

3

Day 3

Arezzo, Monte San Savino, Lucignano, Foiano della Chiana, Camucia, Cortona. Loop via Castello di Gargonza (60–74 km).

4

Day 4

Cortona, Petrignano del Lago, Pozzuolo, Acquaviva, Montepulciano. Loop via Castiglione del Lago (41 or 61 km).

5

Day 5

A day off or a loop via Pienza, San Quirico d’Orcia, and Monticchiello. A loop via Castelmuzio, San Giovanni d’Asso, and Torrenieri (49–81 km).

6

Day 6

Montepulciano, Trequanda, Asciano, Vescona, Arbia, Siena. Loop via Chiuzure (68–86 km).

7

Day 7

Day off.

8

Day 8

A rest day or a loop route via Quercegrossa, Castellina in Chianti, Radda in Chianti, Pianella, and Ponte a Bozzone. Alternative route via Gaiole in Chianti, Rietine, La Madonna di Brolio, and Bossi (64–82 km).

9

Day 9

Siena, Volte Basse, Sovicille, Pievescola, Casole d’Elsa, Volterra (68 km).

10

Day 10

A day off or a loop route via Castel San Gimignano, San Gimignano, Castagno, and Prata d’Era (66 km).

11

Day 11

Volterra, Saline di Volterra, Ponteginori, Guardistallo, Casale Marittimo, Bibbona, San Giusto, San Vincenzo (62 km).

12

Day 12

Free day or loop tour on Elba Island (ferry fees not included) (43–109 km).

13

Day 13

A day off or a loop route via Castagneto Carducci, Sassetta, Suvereto, Cafaggio, and Campiglia Marittima (53 km).

14

Day 14

Transfer from San Vincenzo to Rome (3 hours 30 minutes).

15

Day 15

Transfer to Rome Airport and return to Montreal.

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