Immerse yourself in the purest beauty. This memorable bike holiday takes you to the heart of Tuscany, among superfine red wines, olive groves, and hills designed by cypresses. Simply breathtaking.
Style
Road cycling
Gain
5488 m
Distance
302 km
Level
Medium
Tour overview
EXPLORE CLASSIC TUSCANY BY BIKE AT YOUR OWN SPEED
Immerse yourself in the purest beauty of Italy. This memorable road bike holiday takes you to the heart of Tuscany, among superfine red wines, olive groves, and hills designed by cypresses, wonderful historic centres, and cheerful locals.
You will ride from the Crete Senesi to the lands of the Vino Nobile di Montepulciano and Brunello di Montalcino, passing the “ideal city” of Pienza. Then the medieval atmosphere of Siena and San Gimignano will welcome you. And finally, the Chianti Classico and the romantic routes of the Eroica will close your wonderful journey.
This self-guided tour includes GPS tracks and detailed maps on all the routes for you to follow the itinerary at your own pace. All your luggage is transported from hotel to hotel by our support van. If you run into any issues, the helpful team will be there to assist.
Flights not included. Direct flights available at lastminute.com
Rolling roads across the Italian countryside
Highlights of your cycling trip
Rolling Landscapes
Tuscany's landscape is dreamy and alluring for every road cyclist. These rolling roads beg to be ridden, surrounded by some of Italy's best countryside. Trust us when we say you will definitely fall in love with Italy here.
Charming Accommodation
Each hotel is carefully selected in dreamy locations. You'll feel well rested after each day in the saddle throughout your trip. Every hotel is of a high standard with fantastic facilities to make the trip even more memorable.
Self Guided
Pedal at your pace following the maps and tracks provided during the pre-tour briefing at your arrival. We'll advise you where to stop for lunch and sightseeing along the way. Technical assistance will be available throughout if needed.
Tour destination
TUSCANY - ITALY
Dusty roads and rolling countryside – Tuscany is a dream to ride. Road cyclists should be adding this Italian gem to their hit list. After all, if it's good enough for the pro's then it's good enough for us! Pedal the same routes that are used in the Strade Bianche and discover why we're mad about Tuscany.
Boasting warm and mild weather all year round, Tuscany really is a dreamy destination. The height of summer can get too hot for some in the midday sun. So if you prefer slightly cooler temperatures, perhaps book for spring or autumn dates for a more comfortable ride.
Terrain
Dusty, hilly, and rolling. The roads run beautifully through Italy's interior with tough climbs and fun descents to tackle. Hot summer days really do kick up the dust. Don't forget your glasses and a face covering if you are normally at the back of the peloton!
Culture
Warm and welcoming. Italian hospitality is famous across the globe. Be prepared to be blown away by hearty food and rich flavours, incredible wines, and the all important family feeling that runs throughout the region. Tuscany will leave an imprint on you after your visit.
Il Molinello is a cosy accommodation in the rolling hills east of Siena, better known as the Crete Senesi. Alessandro and Elisa produce high-quality extra virgin olive oil. If you want a super local experience, this is definitely the place!
This family-run farm is the perfect place to start your Classic Tuscany tour.
Beautiful, functional and, above all, ecological. This is our comfortable 4-star hotel, set in the frame of Tuscany’s most beautiful and unspoilt area, reaching from Pienza to the Orcia-Valley, passing along the colourful roads you have always dreamed of.
Another beautiful stop along the journey of this Classic Tuscany tour.
Tour itinerary
Your guide to a perfect cycling tour
Welcome and warm up ride
Tour briefing, bike fitting and warm up ride
Arrival in Tuscany, shuttle or individual arrival at our accommodation in Asciano countryside. Tour explanation, delivery of tour documentation, and careful bike fitting, then possibly warm up ride to the pretty medieval town of Serre di Rapolano.
Overnight: Asciano
Included: Dinner
Asciano to Pienza
Distance
50 km
Climb
1098 m
Across the beautiful villages of Montepulciano and Pienza
Today we ride through the Val d’Orcia, a quintessential Tuscan landscape, made out of rolling hills dotted with cypress trees; its landscape is listed as a UNESCO World Heritage Site. After the marvellous Montepulciano, we end in the pretty Pienza, a real model of Renaissance city.
Overnight: Pienza
Included: Breakfast
Pienza to Montalcino
Distance
43 km
Climb
890 m
In the land of the Brunello di Montalcino wine
From the romantic Renaissance atmosphere of Pienza, heading towards the medieval village of Montalcino, kingdom of the fine Brunello di Montalcino wine. Along the way the beautiful Orcia valley and the majestic Sant’Antimo Romanic abbey.
Overnight: Montalcino
Included: Breakfast
Montalcino to Siena
Distance
55 km
Climb
850 m
From the vineyards of Montalcino to the rolling hills of Siena
A beautiful ride from the vineyards of Montalcino to the rolling Crete Senesi, until the lively but still authentic Siena, the most medieval town of Tuscany.
Overnight: Siena
Included: Breakfast
Siena to San Gimignano
Distance
60 km
Climb
950 m
Across the Val d’Elsa up to the Manhattan of Medieval times
We leave Siena along the Via Francigena route, after the medieval walls of Monteriggioni we continue through the hills around the Val d’Elsa. The ride ends among the high towers of San Gimignano.
Overnight: San Gimignano
Included: Breakfast
San Gimignano to Gaiole in Chianti
Distance
54 km
Climb
1100 m
An Epic day along the Eroica roads
We say goodbye to the unique skyline of San Gimignano then enter the Chianti Classico region, where we will experience some of the dirt roads that have made the Eroica famous all over the world, the iconic vintage bike ride through the Chianti region.
Overnight: Gaiole in Chianti
Included: Breakfast
Gaiole in Chianti to Asciano
Distance
40 km
Climb
600 m
At the origins of Chianti Classico wine
We go through the Chianti wine region, discovering the stunning Brolio Castle, a true symbol of the territory because the official method for the production of Chianti wine was established here in 1872. Then we pass through the ancient thermal baths of Rapolano before ending our day in the countryside of Asciano, chez our friends Elisa and Alessandro.
Overnight: Asciano
Included: Breakfast and Dinner
Recovery ride in Asciano
Arrivederci Amici!
It’s time to say goodbye, but we are sure this part of Italy will touch your hearts and you’ll come again to visit more! Take one last recovery ride in the local area before continuing your journey.
Included: Breakfast
Getting there
Information to help you book your flights and get around.
Any questions about flights and transfers? The Epico team is here for you. Ping us via the chatbot in the corner of your page or send an email to [email protected]
Flying in
Fly in airport options: Florence
When best to arrive: in the morning the day the tour starts
Where the tour starts: we meet in the afternoon in Asciano
Transfers: included from Florence
Flying out
Fly out airport options: Florence
When best to depart: in the evening of the day the tour ends after 17:00
Where the tour ends: in the afternoon in the town of Asciano
Transfers: included to Florence
Tour essentials
What’s included in your cycling trip.
Luxury Accommodation
7 nights in 4* hotels in a shared room with en-suite facilities. Single rooms are available as an additional extra.
GPS Routes
Access to tracks of the route through the RIDE WITH GPS mobile application
Airport Transfers
Transfer to and from Florence Airport is included
Daily Luggage Transfers
Support vehicles will transport your luggage on to the next hotel, so you only have to carry your essentials
What’s not included in your cycling trip.
Flight
Flights are not included in the tour package. Please follow our advice about which flights will be best suited for this tour. Reach out to us if you have any questions about flights.
Travel Insurance
Travel insurance is essential and we always recommend you carry out your own insurance search for your specific needs.
Extra
Bike rental
Only €220 for the entire trip
It’s not always easy travelling with a bike but fear not, road bikes are available for rental for the duration of the tour. To make sure you get the maximum from your bike for your trip, we’ve partnered with some of the best brands in cycling to give you the latest choice of equipment.
With a variety of sizes available, we can ensure your bike fits you perfectly. All rental bikes are mechanically checked and adjusted before each and every hire so you can have peace of mind that your bike will be running smoothly from start to finish!
You can select this option when you proceed to checkout.
Brands and models may vary
Fitted to you and ready to ride!
More things to maximise your cycling trip
EXTRA
Single accommodation
€252 per person for entire trip
If you’d like a whole room to yourself, that’s no problem. For an extra €252 for the trip duration, you can enjoy the comfort of your own room. Just select this option when you proceed to book your tour.
Booking options
Choose when you want to travel
Don't see the travel dates you want or have a special request, such as adding a non-rider, please contact us.
This tour has flexible dates. We can make it start and finish the day you need. Contact us to request alternative tour dates!
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