Tuscany and The Island of Elba
An Enchanting Island Escape
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- A thorough daily itinerary
- Details for exact accommodations
- What to expect
- Travel planning tips
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From the Renaissance city of Florence to the pristine beaches of Elba, Tuscany’s cultural wealth and natural beauty are incredibly rich and varied.
We begin south-east of Florence cycling on the Setteponti Road for a couple of days among infinite olive groves. From there we’ll pedal through the vineyards of the hilltowns of Chianti, and through the twisting streets of Siena. Strolling Siena’s narrow maze of cobblestone walkways is an amazing architectural journey, and the view from Siena’s famous tower will make your head spin!
From Siena we travel through dramatic landscapes to Volterra. Our tour finishes on the enchanting island of Elba. One of the most beautiful islands in Italy, Elba has been recognized for centuries for its elusive beaches, warm crystal waters, mountain vistas, and tranquil villages. We’ll park our bikes, dive into the warm blue waters, and discover why Napoleon chose to exile to this humble paradise.
Tour Essence
- Ride the historic Setteponti Road past olive groves and Renaissance towns
- Discover the world of olive oil on a visit to a local olive oil producer
- Pedal through Chianti’s vineyards and villages in the heart of wine country
- Get a glimpse of the Eroica vintage cycling spirit in Gaiole in Chianti
- Walk Siena’s Gothic streets and climb the Torre del Mangia (UNESCO site)
- Visit the fresco-filled Pilgrims’ Hall at Santa Maria della Scala (UNESCO)
- Enjoy a guided walking tour through Siena and earn about Il Palio and life in a Contrada from a local Sienese insider
- Cycle the open landscapes of the Volterrana with wide Tuscan panoramas
- Join a guided tour of Volterra’s Etruscan ruins and visit the Guarnacci Museum
- Ride to San Gimignano (UNESCO), famed for its skyline of 15 medieval towers
- Relax in Bolgheri with a vineyard lunch and tasting of Super Tuscan wines
- Ferry to Elba Island and settle into its palm-lined, Mediterranean charm
- Explore Elba’s coastline with views of mines, cliffs, and wildflower hills
- Unwind at historic, elegant hotels—from a 17th-century palazzo to a villa
What to Expect
Terrain
Rolling to hillyStart Location
San Giustino Valdarno, ItalyEnd Location
Elba, ItalyMileage
Average Daily: 40 miles Total: 255/310 milesElevation
Average Daily: 2,800/3,700 ft Total: 19,600/25,800 ft
Once you have a trip confirmed, we will feed you a steady diet of additional pre-departure information that includes: How to train, prepare, pack and all the wonderful, inspirational and practical things you want and need to know before you go! Our Travel Advisors will be available to help plan your pre- and post-tour travel.
- Expert, bilingual guides
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Ciclismo jersey and water bottle
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Van support
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Guided walking tours of Siena and Volterra
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1 wine tasting
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1 olive oil producer visit
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Evening of live music
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Group ferry at the end of the tour
What’s Included
- Use of our exclusive carbon road bike, La Classica Ribelle (or Equivalent Carbon Road Bike)
- Garmin Edge Explore GPS loaded with the GPX tracks of your rides
- Two water bottles
- Saddle bag with repair kit
- Optional: Map holder on handlebar
Pedal Options
- Flat pedals
- Half-toe pedals (without straps)
What’s Not Included
- Helmet
- Optional: clipless/SPD pedals with shoes
- Optional: your own saddle
- All accommodations
- All breakfasts
- 2 lunches
- 6 dinners
- Guided walking tours of Siena and Volterra to learn about Etruscans
- Visit the famous wine villages of Greve, Panzano, Radda, and Gaiole in Chianti and learn all about Sangiovese grapes
2025
2026
Start Location
San Giustino Valdarno, ItalyFly Into
FlorenceEnd Location
Elba, ItalyFly Out Of
FlorenceIl Borro Loop
Meals Provided
Lunch, DinnerAverage Mileage
10/15 milesElevation Gain
600/1,300 ftRiding Terrain
Flat and gently rolling with a climb in the extra loopMeals Provided
Lunch, DinnerAccommodations
Villa Cassia di Baccano
Villa Cassia di Baccano is a Tuscany Resort in Italy, near Florence, Arezzo, and Siena, with a fascinating history. Built in the XVII century as a nun’s convent, a Roman noble family, the Cornacchia Palmieri, bought it and made it their Tuscany Villa after WWI. The property has a beautiful garden and swimming pool.
Reggello Loop
Meals Provided
Breakfast, DinnerAverage Mileage
40/45 milesElevation Gain
2,800/3,000 ftRiding Terrain
Undulating with some short steep hillsMeals Provided
Breakfast, DinnerAccommodations
Villa La Grotta
Set in the heart of Tuscany, La Grotta is an elegant Tuscan villa, once home to a local noble family. La Grotta is a typical Tuscan manor house dated late ‘700, perfectly restored and opened to welcome guests who wish to taste the genuine hospitality of Tuscany. The surrounding gardens feature an outdoor swimming pool with views of the Chianti countryside.
Siena
Meals Provided
Breakfast, DinnerAverage Mileage
50 milesElevation Gain
2,800/4,500 ftRiding Terrain
HillyMeals Provided
Breakfast, DinnerAccommodations
Grand Hotel Continentale
The Grand Hotel Continental Siena is a prestigious 5-star boutique hotel nestled in the heart of Siena’s historic center. Housed in the 17th-century Palazzo Gori Pannilini, the hotel showcases original frescoes and elegant Renaissance architecture. Its prime location places guests just steps away from Piazza del Campo and the Duomo di Siena, offering an immersive experience in the rich cultural heritage of Tuscany.
Siena - Rest Day
Meals Provided
BreakfastAverage Mileage
22 milesElevation Gain
1,800 ftRiding Terrain
HillyMeals Provided
BreakfastAccommodations
Hotel Palazzetto Rosso
Palazzetto Rosso Boutique Hotel is located in the heart of the medieval town of Siena. The red brick walls hotel has been hosting travelers since the Middle Ages when traders from all over the world came to Tuscany. A lot has changed since the hotel’s original days, but the original façade remains the same with its traditional wrought-iron ensigns and flares.
Volterra
Meals Provided
Breakfast, Lunch, DinnerAverage Mileage
45/55 milesElevation Gain
4,800/5,400 ftRiding Terrain
HillyMeals Provided
Breakfast, Lunch, DinnerAccommodations
Hotel San Lino
The 4-star Hotel San Lino, established in 1982, is idyllically located within the Medieval defensive walls. The building, a former convent dating back to 1480, has been exquisitely and attentively renovated to preserve the original architectural features and maintain its arcane and historical charm. Enjoy the outdoor swimming pool in what was once the main cloister, a roof terrace, and a restaurant.
S. Gimignano Loop
Meals Provided
BreakfastAverage Mileage
20/40 milesElevation Gain
1,700/4,300 ftRiding Terrain
HillyMeals Provided
BreakfastAccommodations
Grand Hotel Continentale
The Grand Hotel Continental Siena is a prestigious 5-star boutique hotel nestled in the heart of Siena’s historic center. Housed in the 17th-century Palazzo Gori Pannilini, the hotel showcases original frescoes and elegant Renaissance architecture. Its prime location places guests just steps away from Piazza del Campo and the Duomo di Siena, offering an immersive experience in the rich cultural heritage of Tuscany.
Baia Ottone, Elba
Meals Provided
Breakfast, Lunch, DinnerAverage Mileage
35 milesElevation Gain
2,400/2,800 ftRiding Terrain
HillyMeals Provided
Breakfast, Lunch, DinnerAccommodations
Hotel Villa Ottone
5-star Hotel Villa Ottone offers luxurious accommodation in front of the sea on Elba Island. This historic Villa is surrounded by ancient parkland that extends to a private beach. Guests can also enjoy a panoramic restaurant, an outdoor pool, a gym, and a wellness center.
Elba Loop
Meals Provided
Breakfast, DinnerAverage Mileage
35 milesElevation Gain
2,700 ftRiding Terrain
HillyMeals Provided
Breakfast, DinnerAccommodations
Hotel Villa Ottone
5-star Hotel Villa Ottone offers luxurious accommodation in front of the sea on Elba Island. This historic Villa is surrounded by ancient parkland that extends to a private beach. Guests can also enjoy a panoramic restaurant, an outdoor pool, a gym, and a wellness center.
