Tuscany and The Island of Elba
An Enchanting Island Escape
Download a Detailed Itinerary
Our comprehensive itineraries are a one-stop-shop for all the delightful details of our carefully crafted tours, including:
- 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
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Ride through Toscana from mountains to sea
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Visit the famous wine village of Gaiole in Chianti and learn all about Sangiovese grapes
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Experience an all-you-can-eat gelato diet every day
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Discover the magic world of olive oil by taking a tour of a local olive oil producer
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Get a glimpse of the world of the Eroica, the world’s most famous vintage cycling event
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Enjoy walking tours in Siena and Volterra
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Learn about Il Palio di Siena and the life of a Contrada
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Learn about the Etruscans by visiting the Guarnacci Museum
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Ride a spectacular loop on northern Elba and improve your cycling
What to Expect on Your Tuscany Bike Tour
Terrain
Rolling to hillyStart Location
Malva, ItalyEnd Location
Elba, ItalyMileage
Average Daily: 39 miles Total: 263-368 miles
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.
- All accommodations
- Expert, bilingual guides
- All breakfasts, 3 lunches, 6 dinners.
- Guided tours of Siena and Volterra
- 1 wine tasting
- 1 olive oil producer visit
- Live music one evening.
- Post-tour group ferry
What’s Included
- Use of our exclusive carbon road bike, La Classica Ribelle (or Equivalent Carbon Road Bike)
- Garmin Edge Touring 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.
- 1 wine tasting
- Guided 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
Malva, ItalyFly Into
FlorenceEnd Location
Elba, ItalyFly Out Of
Il Borro Loop
Meals Provided
Lunch, DinnerAverage Mileage
10/14 milesRiding Terrain
OndulatingMeals Provided
Lunch, 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.
Reggello Loop
Meals Provided
Breakfast, DinnerAverage Mileage
41/44 milesRiding Terrain
Ondulating 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
50/52 milesRiding Terrain
HillyMeals Provided
Breakfast, DinnerAccommodations
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.
Siena - Rest Day
Meals Provided
BreakfastAverage Mileage
22/40 milesRiding 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
43/53 milesRiding 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
20/39 milesRiding Terrain
HillyMeals Provided
BreakfastAccommodations
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.
Baia Ottone, Elba
Meals Provided
Breakfast, Lunch, DinnerAverage Mileage
34/37 milesRiding 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
36 milesRiding 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.
