Tuscan hills & Elba island cycling escape

Discover the serene charm of tiny villages on this Tuscany bike tour. Savor the unique flavors and scents of a region rich in tranquility and tradition

Cycling through the roads and colors of Tuscany

Experience the “Tuscany hills & Elba cycling escape,” where the rolling hills of Siena and Chianti meet the serene views of the Tyrrhenian Sea.

Cycle through UNESCO-listed landscapes, iconic Tuscan villages, and indulge in renowned wines and cuisine. From the historic charm of Tuscany to the tranquil pace of Elba Island, famously Napoleon’s haven, this tour blends cultural richness with natural beauty for an unparalleled biking adventure.


DURATION: 7 Nights / 8 days
GROUP SIZE: From 4 participants and up to 12
LOCATION: Italy, Tuscany and Elba island
WHEN: Suggested periods are from April to mid of June and from September to end of October

What is included in your Tuscan Hills & Elba Island

  • Welcome briefing.
  • 7 Nights in 5-star boutique accommodation with breakfast and four dinners. 
  • 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 to Elba Island. 
  • 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.

ESCORTED: €4280 per person, min 4 participants in double/twin room.

Basso Road bike. Carbon frame, disk brake and mechanic shift: €360,00
Brand and models may vary in year or color, and an alternative bike of equal value may be provided if the preferred model is unavailable
Officine Mattio high-end Italian Road bike. Carbon frame, disk brake, and electronic shift: € 440,00

E-Bike hire: €315,00

ACTIVITIES AVAILABLE UPON REQUEST: to be arranged and booked during the booking process
Guided walking tour in Siena
Guided walking tour on Elba Island


Tips for guides, travel to/from the start and end points of your trip, meals and activities during your free time. All of the items not included into the services included list above.

Tuscany and Elba island bike tour – A journey into renaissance culture

Cultural activities

The TUSCANY HILLS AND ELBA ISLAND CYCLING ESCAPE offers a rich blend of cultural experiences: from the underrated beauty of Arezzo’s squares to a medieval castle stay, and cycling through UNESCO-listed Siena hills to exploring Elba Island’s ties to Napoleon, this tour connects you deeply with Tuscany’s historical and cultural heritage.

DAy 1
Tuscan Welcome

DISTANCE: 26 miles (43km)

Begin your Tuscan adventure with a transfer from Arezzo train station to a charming medieval village in the hills.

An orientation and warm-up ride await, followed by a welcome dinner at the hotel, setting the perfect start to our journey

MEALS: dinner included

DAy 2
Crete Senesi Discovery

DISTANCE: 37 miles (61km)
ELEVATION GAIN: 3172 ft (967m)

Explore the timeless beauty of Crete Senesi, cycling towards a village shadowed by Monte Amiata. Revel in the ancient landscapes and therapeutic waters that define this region. Breakfast fuels your journey.

MEALS: breakfast included

DAy 3
Through the UNESCO Siena hills

DISTANCE: 43 miles (72km) 
ELEVATION GAIN: 4353 ft (1327m) 

Bike ride to Siena, passing through the UNESCO heritage landscapes of its province. A mid-ride stop at Brolio Castle winery offers a perfect lunch break.

MEALS: breakfast and lunch are included

DAy 4
Chianti’s Charming Loop

DISTANCE: 43 miles (70km)
ELEVATION GAIN: 3280 ft (1000m) 

Navigate a scenic loop through Chianti, known for its exquisite wine and picturesque villages. Enjoy the rich history, vibrant atmosphere, and perhaps a fine espresso.

MEALS: breakfast and dinner are included

DAy 5
Elba Island Transition

DISTANCE: 41 miles (66km) 
ELEVATION GAIN: 4580 ft (1396m) 

A mix of cycling and transfer brings us to Elba Island, a Mediterranean paradise with stunning beaches and vineyards. Experience its exceptional cuisine and wines.

MEALS: All meals provided

DAy 6
Western Elba Coastline

DISTANCE: 44 miles (72km)
ELEVATION GAIN: 5003 ft (1525m) 

Cycle Elba’s western coast for breathtaking views of the sea, charming villages, and pristine beaches. Today’s ride is a feast for the senses.

MEALS: Breakfast included

DAy 7
Eastern Elba Exploration

DISTANCE: 51 miles (83km)
ELEVATION GAIN: 5036 ft (1535m) 

Discover Elba’s east side, including Capoliveri and Porto Azzurro, offering splendid sea views and quaint stops for a rejuvenating cappuccino.

MEALS: breakfast and farewell dinner are included

DAy 8
Farewell and Transfer

Conclude with breakfast before a private transfer to the port for your mainland ferry. Our journey together ends here, but the memories linger.

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