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Fantastic summer colorful sunset landscape in Tuscany. Wonderful flowery grain fields and

Tuscany and Elba Island

How about biking into the beauty?

Ride Your Life Tour Tuscany and Elba Island puts you in touch with inland Tuscany and the main island of its archipelago in a beautiful balance of biking through the UNESCO hills in the Siena and Chianti area and the refreshing feeling of biking overlooking the Tyrrhenian Sea. You'll bike through picturesque landscapes and romantic villages and enjoy its famous wines and cuisine. Tuscany is one of those places where you are a part of perfection and harmony.

Biking through the Tuscany hills and the picturesque medieval villages included in the routes is a unique experience; here, history and the beauty of the landscape are linked together, while moving on the island gives you the sense of a different pace of time. 

Elba Island is known as "Napoleon's Island" due to his exile between May 1814 and February 1815; during his exile, he carried out a series of economic and social reforms to improve the quality of life still visible in the island.


  • Welcome briefing

  • 7 nights in 5-star boutique accommodation;

  • 7 breakfast;

  • 4 dinners;

  • 1 wine tastings

  • 1 cooking class

  • 2 lunches

  • Guided walking tour in Siena

  • Guided walking tour at Elba Island

  • Private transfer from Arezzo train station to the first accommodation

  • Private transfer from Piombino port to the train station

  • Ferry tickets GO/BACK

  • GPS with preloaded routes ready to use

  • Tour Agenda with the day-per-day program;

  • Van support along all of the week with our Italian guide English speaking; includes transfer luggage and support on tour

  • Ride Your Life Cycling jersey

  • Ride Your Life water bottle

*From 4 participants

Price €4530 per person



  • Extra cost for single room: €997,00

  • Officine Mattio high-end Italian Road bike rental: € 350,00 (carbon frame, disk brake, and electronic shift

OM is an Italian artisan bike factory that shares a great passion for cycling with us. The philosophy that guides Officine Mattio is based on a mix of innovative technical solutions and inspiration from the past.

Production, research, and design are Made in Italy.

Day by Day program

DAY 1: Welcome to Tuscany and warm-up.  - Miles/kilometers: 26 / 43 - Elevation gain feet/meters: 2381 / 726 


Private transfer from the close Arezzo train station to our accommodation in a thirteen-century fortified medieval village in the heart of Tuscan hills. 

In the afternoon, we'll have a brief introduction to the trip and a warm-up ride to get confidence with our bikes.

Meals: Dinner is included at the accommodation

DAY2: Miles/kilometers: 37/61 Elevation gain feet/meters: 3172/967

Today's ride takes you to a small village that has managed to preserve the look and atmosphere of times gone. We are in the Crete Senesi, where you recognize the peak of the imposing shape of the ancient volcano Monte Amiata, the source of the thermal waters that flow in many places in the nearby areas.

Meals: Breakfast is included

DAY3: Miles/kilometers: 43/72 Elevation gain feet/meters: 4352 / 1327

We'll ride to Siena this morning through the UNESCO landscape of its province and quiet secondary roads. Along the way, we'll stop at Brolio Castle winery for lunch; this is perfectly located after the majority of the hills of the day and just 25km from Siena.

Meals: Breakfast and lunch are included

DAY 4: Miles/kilometers: 42/70 Elevation gain feet/meters: 3280 / 1000

The clockwise loop ride in the Chianti lets us ride through some of the most representative villages of the area. This is the province of Tuscany where is produced the famous Chianti wine; along the way, we'll pass through some charming villages interesting to explore for their history and atmosphere and maybe stop to enjoy a good expresso.

Meals: Breakfast and dinner are included 

DAY 5: Miles/kilometers: 40/66 Total elevation gain feet/meters: 4579 /1396


Today we'll have a combination of bike ride and transfer to move to Elba Island, the largest of the Tuscany archipelago and part of the Arcipelago Toscano National Park. 
Elba island is a glorious paradise of beach, coastal road to bike, vineyards, sky-blue waters, and outstanding views. On top of this, the island offers delicious cuisine and lovely island wines.

Meals: Breakfast, light lunch, and dinner are included


Miles/kilometers: 43/72 - Elevation gain feet/meters: 5002/1525

Our route today will move along the island's west side's coastline and give us spectacular views of the inland and the sea with sea villages and beaches. 

Meals: Breakfast is included 


Miles/kilometers: 50/83 - Elevation gain feet/meters: 5035/1535

The East side loop includes the Medieval Capoliveri and the seaside Porto Azzurro, two of the most representative villages of the island. The ride offers beautiful views of the sea and inland with several options of stopping to refill your energy with a good cappuccino or to enjoy the visit of the villages you pass through.

Meals: Breakfast and dinner are included 


Breakfast and private transfer to the port to take the ferry back to the mainland.

End of our services.

Meals: Breakfast is included 



This trip is for leaded groups, from a minimum of 4 to a maximum of 12 participants. We believe that small groups give more socializing opportunities and create stronger connections.

Old town and harbor Portoferraio, Elba island, Italy.jpg

This trip aims to give you a memorable bike tour experience along with some of the most beautiful bike rides we may have in Italy. You might experiment much more; this is one of our selections.

The spirit of the trips in RIDE YOUR LIFE is to enjoy the rides at your speed and give you a chance to test your legs at your own pace. None of our bike rides is a race; we know, however, that some riders will be faster than others and that each one likes to keep his/her own pace along the uphill rides; therefore, our way is to enjoy the ride and wait for the last riders at the summits to reconnect the group. Experience is all together! 


Regarding difficulty, the trip includes uphill and some more gentle rolling rides, so we suggest the trip is for intermediate or above-level riders. 

For every ride, you'll find the service of the van support to let you have the comfort of snacks, water, and energy drinks along with the rides. The vehicle follows you in case any group participant needs to or prefers to skip any section of the ride.

Tuscany - Landscape panorama, hills and meadow, Toscana - Italy.jpg
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