Tuscan Hills & Elba Island Cycling Escape

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.

ESSENTIAL DETAILS

DIFFICULTY LEVEL: Easy / Moderate
ROAD SURFACE: Asphalt
SUGGESTED BIKE: Road, E bike
SUPPORT: Guided
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
TEMPERATURES IN THE SUGGESTED PERIOD: 12°C (53.6°) to 24°C (75°F)

What is included in your Tuscan Hills & Elba Island

GUIDED
  • 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.
PRICE and SUPPLEMENTS

ESCORTED: €4280 per person, min 4 participants in double/twin room.
EXTRA COST FOR SINGLE ROOM: €997,00

BIKE RENTAL:
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



NOT INCLUDED

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.

Discover your next adventure: explore our tours

Eternal Pathways – Siena to Rome Gravel Adventure

Rural landscape of the Unesco Siena Hills and the Maremma and Tuscia areas (the South of Tuscany and the North of Lazio). Small undiscovered villages, great food and wines. The route is super quiet and out of the traffic.

Discover the tour

Ancient Trails & Greek Ruins – Western Sicily Gravel Bike expedition

The Interior of Sicily will take you back in time. More than just a bike tour, this adventure is a deep exploration into the heart of Sicilian culture.

Discover the tour

Etna Volcano Dual Ascent: The Ultimate Sicilian Bike Adventure

Discover the thrill of ‘Dual Ascent: The Ultimate Sicilian Bike Adventure,’ combining serene coastal rides with the volcanic landscapes of Mount Etna.

Discover the tour

Balance & Bike: A Mindful Cycling Retreat, bike camp at a Sicilian agriturismo

Discover Serenity and Adventure with our Sicilian Agriturismo Bike & Yoga Retreat. Dive into a rejuvenating six-day experience that combines tranquil yoga sessions, scenic bike rides, and authentic Sicilian culinary delights, including hands-on pizza-making.

Discover the tour

Stelvio & beyond: Italy’s epic climbs tour

Embark on a cycling journey across Italy's iconic climbs, including the legendary Stelvio, on our "Stelvio & Beyond Cycling Tour".

Discover the tour

Etna Volcano Dual Ascent: The Ultimate Sicilian Bike Adventure

Bike adventure in Sicily. Image of the volcano Etna.

Etna Volcano Dual Ascent:
The Ultimate Sicilian Bike Adventure

Cycling experience in Sicily

Explore Sicily’s lesser-known paths and celebrated climbs with our versatile bike tours. Catering to both self-guided adventurers and those preferring guided insights. This journey takes you from the sparkling Mediterranean shores to the impressive volcanic terrain of Mount Etna. Experience the diverse landscapes, ancient culture, and culinary richness that make Sicily a unique place to discover.

Savor the local cuisine, from traditional dishes to the beloved granita, and let the quiet roads past ancient ruins and vibrant landscapes inspire your journey. Available as a self-guided adventure, with optional customization for the Aeolian Islands, ‘Dual Ascent’ is your gateway to Sicily’s soulful energy and serenity.

Choose your date in 2024 and let the Sicilian adventure begin!

ESSENTIAL DETAILS

DIFFICULTY LEVEL: Moderate / Difficult
ROAD SURFACE: Asphalt
SUGGESTED BIKE: Road, E bike
SUPPORT: Guided and Self-Guided
DURATION: 6 Nights / 7 days
GROUP SIZE: From 4 participants and up to 12
SELF GUIDED: From 1 participant
LOCATION: Italy, Sicily island
WHEN: Suggested periods are from April to mid of June and from September to end of October. 1 scheduled group departure for this trip: September 30
TEMPERATURES IN THE SUGGESTED PERIOD: 16°C (60.8°F) and 23°C (73.4°F) by the coast and 6°C (43°F) on Etna

What is included in your ultimate Sicilian bike adventure

SELF GUIDED
  • 6 Nights in 4 star hotel.
  • 6 Breakfasts.
  • 4 Dinners.
  • 2 Wine tasting and lunches.
  • GPS tracks.
  • Tour agenda of the trip with maps, graphs, and daily program.
  • Arrival, private transfer from Catania Airport.
  • Luggage transfer.
  • Ride Your Life Cycling jersey.
  • Ride Your Life water bottle.
PRICE and SUPPLEMENTS

SELF GUIDED: € 1950,00 Price per person based on 2 participants in double/twin room
GUIDED: €2825 per person, min 4 participants in double/twin room
EXTRA COST FOR SINGLE ROOM: €325,00

BIKE RENTAL:
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

ACTIVITIES AVAILABLE UPON REQUEST: to be arranged and booked during the booking process
Post trip extension in Taormina, it includes a guided walking tour in town and Greek theater

Post trip extension on the Etna, it includes a guided excursion of the volcano with a volcanologist

GUIDED
  • 6 Nights in 4 star hotel.
  • 6 Breakfasts.
  • 3 Light lunches.
  • 4 Dinners.
  • 2 Wine tastings.
  • Van Support .
  • Two Italian-English speaking tour leaders: 1biking with you; 1on van support (from 7pax).
  • GPS tracks.
  • Tour agenda of the trip with maps, graphs, and daily program.
  • Energy gels, drinks, and bars for the rides.
  • One cumulative arrival, private transfer from Catania Airport.
  • Ride Your Life Cycling jersey.
  • Ride Your Life water bottle.

NOT INCLUDED

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.

Bike adventure in Sicily – Nature, history great food and people

Cultural activities

We have included two striking cultural activities in your Sicily bike adventure. The first will take place at the top of Mount Tauro. Taormina is a natural terrace overlooking the sea and a dream for anyone. A unique natural beauty makes this city the pearl of the Ionian Sea, the most famous and important place in all of Sicily. 

Its historic center is full of monuments and a spectacular Hellenistic theater that offers an amazing panorama of the turquoise sea and a view that extends to the coasts of Calabria, the city of Syracuse and the summit of Etna. 

The second activity includes a guided tour of the Etna volcano. It is one of the highest volcanoes in Europe. Visitors can explore the smoking volcanic craters and lava fields of the mountain. Are you going to miss it? 

Bike adventure in Sicily for you

Experience the cycling trip of your dreams on the magical Italian island of Sicily. Cycle between volcanoes and picturesque places that will take your breath away.

DAy 1
Arrival & Warm-Up

DISTANCE: 13 miles (22km) 
ELEVATION GAIN: 938 ft (286m)

Begin your Sicilian cycling adventure with a transfer from Catania airport to your first hotel, where a tour briefing and a warm-up ride await. The evening concludes with a shared dinner, setting the tone for the journey ahead.

MEALS: dinner included at the hotel Terre di Eolo

DAy 2
Capo Milazzo and its castle

DISTANCE: 43 miles (72km)
ELEVATION GAIN: 2500ft (762m)

Explore quiet coastal roads to Capo Milazzo, riding the early training routes of Vincenzo Nibali and ascending Tindari. Discover Milazzo, gateway to the Aeolian Islands, before returning to the hotel for a well-deserved Sicilian dinner and wine tasting.

MEALS: Breakfast and dinner included

 

DAy 3
Fiumara

DISTANCE: 47 miles (77km) 
ELEVATION GAIN: 5344 ft (1629m) 

Pedal through the unique landscapes of Sicily’s riverbeds, or “fiumara,” en route to Sella Mandrazzi, a climb featured in the Giro d’Italia. Experience the blend of natural beauty and cycling challenge.

MEALS: Breakfast is included

Day 4
Etna

DISTANCE: 39 miles (64km)
ELEVATION GAIN: 6194 ft (1888m) 

We’ll ride to the Etna area this morning, with stunning sea and countryside views, culminating in the ascent to Portella Mandrazzi, known from recent Giro editions. The day ends with dinner at the hotel, reflecting on the ride’s highlights.

MEALS: Breakfast and dinner at the hotel Picciolo Etna Golf Resort

Day 5
Etna North

DISTANCE: 39 miles (63km) 
ELEVATION GAIN: 5456 ft (1663m) 

Tackle Etna from its west/north side, immersing in the volcanic landscape’s allure. Today’s leisurely lunch punctuates the ride, with breakfast and wine tasting highlighting local flavors.

MEALS: Breakfast, light lunch and wine tasting included

Day 6
Etna South

DISTANCE: 64 miles (104km)
ELEVATION GAIN: 8156 ft (2486m) 

Conquer Etna’s south side in this trip’s most challenging ride, reaching the volcano’s summit. Celebrate your achievements with a farewell dinner, marking the end of an epic Sicilian cycling tour.

MEALS: Breakfast and dinner included

Day 7
Departure!

Breakfast and cumulative transfer to Catania airport or opt to extend your vacation with two nights in Taormina to immerse yourself further in Sicily’s beauty, exploring its historical sites and relaxing by the stunning coastline.

 

Discover your next adventure: explore our tours

Eternal Pathways – Siena to Rome Gravel Adventure

Rural landscape of the Unesco Siena Hills and the Maremma and Tuscia areas (the South of Tuscany and the North of Lazio). Small undiscovered villages, great food and wines. The route is super quiet and out of the traffic.

Discover the tour

Tuscan Hills & Elba Island Cycling Escape

What if we told you that we have the ideal bike tour in Tuscany?

Discover the tour

Ancient Trails & Greek Ruins – Western Sicily Gravel Bike expedition

The Interior of Sicily will take you back in time. More than just a bike tour, this adventure is a deep exploration into the heart of Sicilian culture.

Discover the tour

Balance & Bike: A Mindful Cycling Retreat, bike camp at a Sicilian agriturismo

Discover Serenity and Adventure with our Sicilian Agriturismo Bike & Yoga Retreat. Dive into a rejuvenating six-day experience that combines tranquil yoga sessions, scenic bike rides, and authentic Sicilian culinary delights, including hands-on pizza-making.

Discover the tour

Stelvio & beyond: Italy’s epic climbs tour

Embark on a cycling journey across Italy's iconic climbs, including the legendary Stelvio, on our "Stelvio & Beyond Cycling Tour".

Discover the tour

Open chat
Hello ????
Can we help you?