Tuscany Road Biking Tour
Tuscany Road Biking Tour

Tuscany Road Biking Tour

7 days

Beautiful cathedra in ItalyCity plaza in Tuscany, ItalyGroup of cyclists riding road bikes in TuscanyAutumn views from Piaza in TuscanyBikes parked near hotel in TuscanyStunning Italian architecture in TuscanySunset over the Tuscany vineyardsRiding road bikes in TuscanyVineyards in ItalySmall swimming pool near hotel in TuscanyHilly cycling path in Tuscany, ItalyCyclist riding the road bike in Tuscany

Cycle for a stellar week through the Tuscan countryside

The Tuscany Road Biking Tour will take you through some of the most picturesque landscapes in the world as you expore the Italian countryside. Ride through immersed in history and through unique scenery. This is a tour that allows you to discover the real Italy.

In a region that has made hospitality an art, you will enjoy a combination of excellent accommodation and acclaimed restaurants, carefully and personally selected from those specialized in local cuisine. The objective of this cycling adventure is to ensure that you discover new, captivating places, enjoy the best the area offers, and take advantage of the adventurous nature of road biking. You will ride through two regions of Italy, both with scenery to die for that you’ll appreciate from the saddle.

Highlights of the Tuscany Road Biking Tour

Ride for a week in gorgeous Tuscany, one of the gems of Italy’s world-class travel scene.
Challenge yourself on some rides and sit back to enjoy the view on others.
Explore villages with gorgeous churches and monasteries that date back centuries.
Between rides, revel in the first-class cuisine and hospitality of Tuscany at restaurants and hotels.

Prices

From $3,225USD
7 days
Difficulty
Guided
Hotels
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Tuscany Road Biking Tour

Tuscany Road Biking Tour Itinerary

Day 1 Arrival in Siena

When you arrive in Siena, you’ll enjoy a welcome drink, get your bike fitted, and then have dinner with the group.
Overnight Location: Hotel in Siena
Distance: None
Meals: Dinner

Day 2 Siena and Chianti Loop Bike Ride

You first ride takes place in the Chianti Hills area. This area, famous all over the world, is the birthplace of Chianti wine. You’ll start your cycling day riding through rolling hills surrounded by vineyards.

Once you arrive in Radda in Chianti, you’ll stop for a cappuccino and cornetto in the magnificent old square. After your stop, keep on riding with views of vineyards and historic villages. At the hotel, wind down in the swimming pool and get ready for a delicious dinner.
Overnight Location: Hotel in Siena
Distance: 70km
Meals: Breakfast, dinner

Day 3 Bike to Montalcino

After breakfast, you’ll ride towards Monteroni D’Arbia on quieter secondary roads through the magnificent Val d’Arbia. You will then continue towards Asciano, with its splendid Monte Oliveto Maggiore abbey. Riding up and down between hills and cypress trees, you will arrive at Buonconvento in the Ombrone Valley.

The final stretch of the day’s ride takes you to your destination, Montalcino. This town is well-known for its production of the famous Brunello wine, which is never sold less than five years after the grape harvest.
Overnight Location: Hotel in Montalcino
Distance: 75km
Meals: Breakfast, dinner

Day 4 Montalcino Loop Bike Ride

Today is all about the unique Val D’Orcia as you ride on peaceful backroads. You’ll start your day with the descent from Montalcino to Torrenieri, then you will ride through ancient villages, where you’ll have breaks for cappuccino and espresso.

Stop to visit the splendid San Quirico d’Orcia, where you can have a lunch in a typical “trattoria” to recovery energy for taking on the demanding Montalcino ascent. An exclusive dinner in this fairytale village will end your day.
Overnight Location: Hotel in Montalcino
Distance: 68km
Meals: Breakfast, dinner

Day 5 Bike to Acquapendente

San Quirico d’Orcia is the first village you’ll encounter today, and the spa in its hamlet of Bagno Vignoni is famous. Radicofani, a wonderful village dominated by a castle, is waiting for you further along the way.

Finally, you’ll ride into the Lazio region at Acquapendente, where you will be justly rewarded for your efforts with a visit to the historical centre and an excellent dinner.
Overnight Location: Hotel in Cantiano
Distance: 72km
Meals: Breakfast, dinner

Day 6 Bike to Lake Bolsena

Ride back, briefly, into the Tuscany region and arrive in Pitigliano, with its characteristic historical center called “Little Jerusalem” because of the presence of an ancient Jewish community. After leaving Pitigliano, head for Lake Bolsena, where Civita di Bagnoregio is waiting for you. Here, a very different landscape will provide the ideal setting for an evening in good company with a delicious dinner.
Overnight Location: Hotel in Bolsena
Distance: 65km
Meals: Breakfast, dinner

Day 7 Departure

After a wonderful week, you’ll head back to Siena to depart. Safe travels!
Overnight Location: None
Distance: None
Meals: Breakfast

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Tuscany Road Biking Tour Price and Dates

This guided tour is always run as a group tour where you’d be joining a group, however, custom private tours can be organized for groups of 4 and more. Please contact us with your preferred date and the number of people in your group and we will create the itinerary just for you.

Prices below are per person:

Apr 27, 2025
May 03, 2025
From Siena, Italy
To Bolsena, Italy
USD$3,225
7 days / 5+ Spaces Left
May 18, 2025
May 24, 2025
From Siena, Italy
To Bolsena, Italy
USD$3,225
7 days / 5+ Spaces Left
Jun 01, 2025
Jun 07, 2025
From Siena, Italy
To Bolsena, Italy
USD$3,225
7 days / 5+ Spaces Left
Jun 06, 2025
Jun 12, 2025
From Siena, Italy
To Bolsena, Italy
USD$3,225
7 days / 5+ Spaces Left
Sep 07, 2025
Sep 13, 2025
From Siena, Italy
To Bolsena, Italy
USD$3,225
7 days / 5+ Spaces Left
Sep 21, 2025
Sep 28, 2025
From Siena, Italy
To Bolsena, Italy
USD$3,225
7 days / 5+ Spaces Left
Oct 05, 2025
Oct 11, 2025
From Siena, Italy
To Bolsena, Italy
USD$3,225
7 days / 5+ Spaces Left

Accommodation on the Tuscany Road Biking Tour

This tour is based in hotels. Hotels on this trip are 3 and 4-star and offer modern conveniences that can make this trip more pleasant. Rooms may have fireplaces or access to amenities such as hot tubs, steam rooms, or private decks to lounge on.

In some cases, the accommodation listed below may need to be substituted for other comparable accommodations.

Single Rooms and Solo Travelers
Rooms are double occupancy. You can pay a supplement of $395 USD to have a private room in a hotel where possible. Solo travellers may be required to pay a supplement.

Hotels on Standard Tour

Sangallo Park Hotel ★★★★★

This approachable and relaxed hotel offers a sundeck and pool for you to relax on, as well as cozy rooms and wonderful hospitality.

Hotel dei Capitani ★★★★

With W-Fi, a pool, and pretty terraces, you’ll be able to unwind at this hotel. Enjoy exposed beams and other nice touches in the décor.

Night 5

Sant Apollinare Farmhouse

An authentic Italian countryside farmhouse welcomes you here. Get to know the gracious hosts who can’t wait to make your stay a special one.

Hotel Royal in Bolsena ★★★

You’ll want to laze away next to the gorgeous outdoor pool at this hotel, although the nearby lake is also a plus. Enjoy romantic vibes and pretty rooms here.

What’s Included in the Tuscany Road Biking Tour?

Meals

6 breakfasts and 6 dinners are included.

Accommodations

Accommodations for 6 nights are included.

Transportation during the Tour

Transportation for this tour will include a minibus, both for the transport of your luggage and for any type of assistance that may be required, and the presence of a technical guide cycling alongside you. Airport transfers are not included, however, you will be transferred to/from Alba Train Station.

Also Included

  • Minibus assistance
  • Taxes
  • Technical bike guide and assistance
  • Technical bike shirt
  • Station and hotel transfers

Not included

  • Tips
  • Laundry
  • Drinks at dinner
  • Medical insurance
  • Lunches
  • Anything not mentioned as included

Optional Extras

  • Additional nights before or after the tour
  • Single occupancy upgrades
  • Optional activities or excursions
  • Bike rental:
    • Road bike
    • E-road bike

Frequently Asked Questions about Tuscany Road Biking Tour

Specializing exploring Italy by bike, Road Bike Tours Italy operates with an attention to detail that allows each tour to capture the wishes of the traveller. Their bikes are meticulously maintained and their team strives for total customer satisfaction.

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Map of Tuscany Road Biking Tour

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Is this tour for me?

We rate this tour as a 3/5. Each day you’ll be riding between 60 and 80km, so the tour is suitable for intermediate cyclists.

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