Grand Tour 2027
Duration: 6 days and 5 nights
Europe
Italy
Tuscany – Self-guided
A Cycling Vacation Through Valleys and Fine Dining
Starting at
4599$
per person
Duration
13 days
12 nights
Level
Level:
4 - Advanced - rolling and mountainous - 50 to 90 km
The Dream Life
Tuscany is a dream come true! Life is good in this Italian region, where every kilometer you travel reveals a hamlet even older and more picturesque than the last, and every turn reveals 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, wherever you look, art and history come together. There’s no better way to explore them than on two wheels!
Go Self-guided
With the “ Self-guided ” package, enjoy your trip on your own terms, with complete independence. We’ll provide you with the itinerary and book your accommodations—the rest is up to you!
Dates and Prices
Date*
Duration
Prices starting at
Note
( * Please contact us to check availability. )
Package includes
transportation between the airport and the hotel at the destination, both on the way there and on the way back;
12 nights in a three-star hotel, double occupancy;
12 breakfasts and 2 dinners;
- luggage transport between each stopover city (one piece per person, maximum 20 kg) as well as transport of the bike box;
- GPX data, maps, and daily itineraries in electronic format;
- information to ensure a smooth trip: contact information and phone numbers for transportation providers at the destination;
- bike shops, an emergency phone number, etc.;
- taxes;
Not included: airfare for the passenger, their luggage, and their bicycle; equipment, such as the bicycle; a guide; mechanical assistance and access to a support vehicle; expenses in the event of a mechanical or physical mishap; coverage under the Travel Agents’ Customer Compensation Fund (FICAV), which provides $1 per $1,000 and the applicable discount.
The land portion price listed is based on double occupancy. For more information, including how to book a flight, please contact us.
Package includes
transportation between the airport and the hotel at the destination, both on the way there and on the way back;
12 nights in a three-star hotel, double occupancy;
12 breakfasts and 2 dinners;
- luggage transport between each stopover city (one piece per person, maximum 20 kg) as well as transport of the bike box;
- GPX data, maps, and daily itineraries in electronic format;
- information to ensure a smooth trip: contact information and phone numbers for transportation providers at the destination;
- bike shops, an emergency phone number, etc.;
- taxes;
Not included: airfare for the passenger, their luggage, and their bicycle; equipment, such as the bicycle; a guide; mechanical assistance and access to a support vehicle; expenses in the event of a mechanical or physical mishap; coverage under the Travel Agents’ Customer Compensation Fund (FICAV), which provides $1 per $1,000 and the applicable discount.
The land portion price listed is based on double occupancy. For more information, including how to book a flight, please contact us.
Additional Information
Departure/Return
Rome-Fiumicino Airport
Rome-Fiumicino Airport
Route rating: 4
Fairly difficult route: hilly and mountainous, with relatively steep climbs; 50 to 90 km.
Additional Information
Departure/Return
Rome-Fiumicino Airport
Rome-Fiumicino Airport
Route rating: 4
Fairly difficult route: hilly and mountainous, with 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: 173 km / Long route: 824 km
1
Day 1
Meet at the Rome airport and transfer to Montepulciano (3 hours).
2
Day 2
A day off or a loop route via Acquaviva, Valiano, Salcheto, and Cervognano. Alternative route via Pietraia, Ferretto, Castiglione del Lago, Casmaggiore, and Pozzuolo (42 or 69 km).
3
Day 3
Free day or loop route via Pienza, San Quirico d’Orcia, and Monticchiello. Alternative route via Castelmuzio, San Giovanni d’Anso, and Torrennieri. (48 or 83 km).
4
Day 4
Free day or loop route via Sant’Albino, Chianchiano Terme, and Pienza (46 km).
5
Day 5
Montepulciano, Trequanda, Asciano, Arbia, Siena. Optional route via Chiusure. (66 to 86 km).
6
Day 6
A day off or a loop via Asciano, Monteroni d’Arbia, and Corsano (69 km).
7
Day 7
A day off or loop routes via Ponte A Bozzone, Lecchi, Radda in Chianti, and Quercegrossa. Alternative route via San Felice, Villa, Castelnuovo Beradenga, and Gaiole in Chianti. (64 to 92 km).
8
Day 8
Siena, Sovicille, Rosia, Frosini, Ciciano, Monterotondo, Suvereto, San Vincenzo. (107 km).
9
Day 9
A day off or a loop route via Cafaggio, Follonica, Pratoranieri, Riotorto, and Venturina Terme. Alternative route via Massa Marittima and Valpiana. (76 or 95 km).
10
Day 10
A day off or a loop via Elba Island (39 to 109 km).
11
Day 11
A day off or a loop route via Castagneto Carducci, Sassetta, Suvereto, San Lorenzo, and Campiglia Marittima (63 or 68 km).
12
Day 12
Transfer from San Vincenzo to Rome (3 hours). Rest of the day at leisure.
13
Day 13
Transfer to Rome-Fiumicino Airport.
Contact Us
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