A link to reset your password has been sent to your email


Change language & currency




Change language & currency



Cycling Tour in Italy

Tuscany is one of the most beautiful and famous destinations for a bike tour. Cities such as Florence, Siena, San Gimignano, and Pienza are examples of Renaissance architecture and are listed as UNESCO World Heritage sites. Visiting these places by bicycle, pedaling through the hills and Sangiovese vineyards in the Chianti Classico region is the perfect cycling holiday: peaceful countryside, excellent backroads, tasty food, renowned wine, and cheerful locals.

Key information

  • Trip type: Self-guided
  • Starts in: San Gimignano
  • Ends in: San Gimignano
  • Total Distance: 305 kms / 190 miles
  • Type of bike: E-bike touring, Trekking bike, Road bike, and E-road bike (not included in the price)
  • E-bike: Available for rent for 400 EUR


  • 7 riding days
  • Welcome meeting and tour briefing
  • Maps, route notes or GPS tracks
  • Luggage transportation inn2inn
  • Telephone assistance
  • Water bottle
  • 7 breakfasts
  • 7 nights in nice hotels (4-star or agritourism)

8 days with instruction
Hide all


You will be accommodated in nice hotels (4-star or agritourism).

Hotel Dei Capitani

Hotel dei Capitani is a charming 3-star historic bike friendly property in Montalcino, Val d’Orcia Tuscany. Stunning views, good restaurant and pool.

Hotel Corsignano

Hotel Corsignano is a charm 4-star bike friendly accomodation close located from the historic heart of Pienza. Unique rooms, good breakfast, and bike storage make it a perfect base for cycle tourists.

Hotel La Pace

Nice bike hotel in a renovated ancient building right in Asciano Downtown with a restaurant, garden, and pool perfect for a post-ride relax.

Relais Vignale & Spa

Ancient 18th-century Villa, located in a green oasis of Radda in Chianti, fully reconstructed with an elegant, cozy interior and perfect for cycling tourists.

Bel Soggiorno

Hotel Bel Soggiorno is the perfect place for cycling enthusiasts in San Gimignano. Set within typical 14th-century buildings, it’s a walking distance from the main square and the Porta San Giovanni.

Hotel Villa Betania, Florence

Villa Betania is a bike-friendly hotel in Florence surrounded by a beautiful garden, close to the historical center, and easily reachable by bike from the Chianti Region.

Hotel Italia

An intimate and elegant three-star property owned and operated by a Siena family, totally renovated and within walking distance from the historical district.


About the Program

This bike tour is suitable for all cycle tourists. Perfect for hybrid bikes, fantastic for e-bikes which help overcome some hills, and also excellent for avid cyclists who prefer road bikes.

If you’re new to Tuscany or wish to explore it in the most immersive way, this bike tour from the saddle is the perfect choice.

What to Expect Cycling a Classic bike tour in Tuscany:

  • Brunello di Montalcino, Nobile di Montepulciano and Chianti wines
  • The amazing towns of Siena, Pienza, Montalcino and San Gimignano
  • The Crete Senesi landscape
  • The Eroica routes
  • The tasty Extra Virgin Olive Oil
  • Ride through the Renaissance

Level of Support: Self-Guided Bike Tour

A Self-Guided Bike Tour is a type of cycling adventure where you have the freedom to plan and navigate at your pace. The dedicated tour guide and support team will handle hotel bookings, logistics, and baggage transport, ensuring you enjoy a hassle-free and carefree experience.

Cycling style: Active

Stages up to 70 km per day with a maximum of 1300 meters of climbing. Those tours appeal to riders used to train a bit, with some “tasty” climb. Usually you are back at the hotel in the early afternoon.

For guests that want more riding, they can add extra loops to regular stages.


Day 1: Benvenuti in Toscana! (Warm Up Ride)

Tour briefing, bike fitting and warm up ride

They suggest you arrive at Florence airport. Depending on your needs, they can provide a shuttle from Florence Airport or arrange to meet you directly at your accommodation in the city center of San Gimignano.

San Gimignano, known for its many scenic towers and long history, is a UNESCO World Heritage Site and one of Italy’s first independent communes. They will start with a mandatory toast using a local wine, such as the ancient Vernaccia di San Gimignano. Following this, you will introduce the tour in detail. After a careful bike fitting, you are ready for a warm-up ride to the picturesque medieval town, a perfect beginning to your bike tour in Tuscany.

  • Overnight: San Gimignano
  • Included: –

Day 2: From San Gimignano to Radda in Chianti

  • Distance: 55 kms / 34.2 miles
  • Elevation: 1100 m / 3609 ft

An Epic day along the Eroica roads

A Classic bike tour in Tuscany can’t start without a wonderful ride through the Sangiovese vineyards. This will be the scenario you’ll cross when leaving San Gimignano towards the Chianti Classico region.

In the past, this area was the scene of fierce clashes between the cities of Florence and Siena, disputing over these lands for a long time. The legend of the black rooster, the symbol of the region, and the logo of all the original Chianti wines tell how the border was made to end that never ending war. Nowadays, it’s a place of wonderful serenity and beauty.

But let’s not forget you are also in the realm of the Eroica, the iconic vintage bike ride across the Chianti region, so you will have an exciting taste of the Strade Bianche experience, gravel roads with well-trodden surfaces where it will be fun and romantic to ride.

The route winds through the pretty villages and countryside of Castellina in Chianti and Radda in Chianti, where you will spend the night.

  • Overnight: Radda in Chianti
  • Included: Breakfast

Day 3: From Radda in Chianti to Asciano

  • Distance: 50 kms / 31.1 miles
  • Elevation: 630 m / 2067 ft

At the origins of Chianti Classico wine

Let’s cross the Chianti region, and conquer the Brolio Castle by climbing among cypress trees.

This stunning property is probably the most important symbol of the Chianti area. It belongs to the noble Ricasoli family, of which the most illustrious representative was the baron Bettino di Ricasoli, a prominent politician of the just Kingdom of Italy.

But, above all, he was a researcher and wine entrepreneur of great foresight. After years of research and experimentation, in 1872, the Baron finally defined a method that became the official formula for producing Chianti wine.

You’ll pedal coasting the fortified walls of the Castle. Then, you’ll immerse yourself in the vineyards in the valley. You could have an aperitif at the classy Rapolano Thermal Baths, with great views over the bare Senesi Hills.

  • Overnight: Asciano
  • Included: Breakfast

Day 4: From Asciano to Pienza

  • Distance: 50 kms / 31.1 miles
  • Elevation: 1100 m / 3609 ft

Across the beautiful villages of Montepulciano and Pienza

Today, you’ll 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.

The scenery changes from dry and brown in fall and winter to emerald green and blossoming in spring to the fantastic golden fields in summer. You’ll pass through Montepulciano, where a stop is mandatory to taste one of the best Italian wines: the Vino Nobile di Montepulciano docg.

You’ll end up in the amazing village of Pienza, known as the “ideal city” and considered to be the incarnation of a Renaissance utopia, a UNESCO World Heritage Site as well. Here, you can also taste some great Pecorino cheeses made by local shepherds settled here a few generations ago from the island of Sardinia.

  • Overnight: Pienza
  • Included: Breakfast

Day 5: From Pienza to Montalcino

  • Distance: 40 kms / 24.9 miles
  • Elevation: 890 m / 2920 ft

In the land of the Brunello di Montalcino wine

You’ll leave the romantic Renaissance atmosphere of Pienza, heading towards the kingdom of Brunello di Montalcino, one of the world’s most renowned and precious wines.

The itinerary winds its way through barren fields, woods, olive groves, and vineyards, of course, beautiful vineyards planted with Sangiovese grapes, called “Brunello” in this area.

After crossing the river Orcia, you meet the majestic Sant’Antimo Romanic abbey, marvelously immersed in the countryside. If lucky, you could listen to the monks’ Gregorian chant, a unique experience.

The day’s last climb leads you to the village of Montalcino, which, in addition to the pride of a great wine, can also flaunt a beautiful medieval town.

  • Overnight: Montalcino
  • Included: Breakfast

Day 6: Montalcino to Siena

  • Distance: 50 kms / 31.1 miles
  • Elevation: 850 m / 2789 ft

From the vineyards of Montalcino to the rolling hills of Siena

From the top of Montalcino hill, an exciting descent takes you under the medieval walls of the ancient city of Buonconvento. Then you’ll go up through the typical landscapes of the “Crete Senesi”, made up of rolling hills, gullies, lonely farmhouses, and small parish churches.

Riding along the landscapes you have admired many times in postcards and photos of Tuscany will provide unique emotions.

The day ends right in Siena, a lively and authentic city. Siena is the most medieval town of Tuscany, divided into “Contrade” (districts), and famous for its Palio, a medieval horse race taking place twice a year in the Piazza del Campo square.

Today, you’ll taste the energetic Panforte, the typical Siena spice cake made of nuts and candy fruit, a perfect snack for bike riding!

  • Overnight: Siena
  • Included: Breakfast

Day 7: Siena to San Gimignano

  • Distance: 60 kms / 37.3 miles
  • Elevation: 950 m / 3117 ft

Across the Val d’Elsa up to the Manhattan of Medieval times

Shortly after leaving Siena, you’ll meet the ancient walled village of Monteriggioni. Its medieval walls are almost intact, covering a length of 570 meters and interspersed with 14 towers and two gates, the Porta Franca (towards Siena) and Porta S. Giovanni (towards Florence).

Siena built the village on a hill dominated and monitored by the Via Cassia / Francigena. Its ideal position made it possible to control the valleys in the direction of Florence, a historic rival of Siena, which was visibly expanding its territory then.

The ride will lead you to San Gimignano, a Unesco heritage site thanks to its many scenic towers and long history, one of the first independent communes of Italy. Make sure to have time for an aperitif with a proper Vernaccia di San Gimignano, an ancient wine with a distinctive character.

  • Overnight: San Gimignano
  • Included: Breakfast

Day 8: Departure

Arrivederci Amici!

It’s time to say goodbye, but they know that Tuscany touched your heart and you want to be back in the Med in one of Mediterras bike tour destinations!

  • Overnight: –
  • Included: Breakfast


You can bring your own bike or rent one from them, they offer great bikes from selected Italian and international brands: road bikes, leisure cycling, mountain bikes, e-bikes, all in perfect working conditions.

  • E-bike touring (225 EUR)
  • Trekking bike (135 EUR)
  • Road bike: Carbon + Ultegra / 105 (220 EUR)
  • E-road bike (400 EUR)


Province of Siena, Tuscany

This tour will take place in the Province of Siena, Tuscany.

You will arrive to and depart from San Gimignano.


The following meals are included:

  • Breakfast

What's included

  • Welcome meeting and tour briefing
  • Maps, route notes or GPS tracks
  • Luggage transportation inn2inn
  • Telephone assistance
  • Water bottle
  • 7 breakfasts
  • 7 nights in nice hotels (4-star or agritourism)

What's not included

  • Flights
  • Airport transfers
  • Local taxes (approximately 15 EUR)
  • Any meals or beverages not indicated as included
  • Travel to and from the tour start and end
  • Any private expenses

How to get there

Recommended Airports

Cancellation Policy

  • A reservation requires a deposit of 30% of the total price.
  • The deposit is non-refundable, if the booking is cancelled.
  • The rest of the payment should be paid on arrival.
8 days / 7 nights
from --

This vacation is available all year round, please select an arrival date below.


Low season


  • May 11 – June 21
  • September 14 – May 10, 2025


High season


  • June 22 – September 13

Select your package:

For this organizer you can guarantee your booking through Tripaneer.com. All major credit cards supported.

Why choose Tripaneer.com

Largest Selection
Friendly Customer Service
Offers for every budget
Best Price
Don't miss out! Join our mailing list to get inspiration, tips & special offers sent directly to your inbox.
Served by www:8000

Logging out

of Tripaneer websites