Included: Experienced English-speaking guides with extensive knowledge of the area 6-day guided bike tour in Tuscany Accommodation for five nights in superior hotels (double room with ensuite bathrooms) All breakfasts from Day 2 to Day 6 Lunch and dinner as indicated in the itinerary Two wine tastings Snacks and drinks along the way All maps, trip notes, and detailed route directions GPS: Offline maps and voice navigation All shuttles and technical assistance Van support All baggage transfers Water bottle Sales taxes Add-ons Bike rental Single supplement Not included: Airfare to Italy Train to Chiusi Meals not indicated in the itinerary Beverages Laundry expenses Personal expenses Guide gratuities — optional Travel and medical insurance — optional

How fit do I need to be?

This guided bike tour in Tuscany requires a good fitness level and previous cycling experience. You should be comfortable in the saddle for 4 to 6 hours per day and have enough stamina for six consecutive days of cycling through hilly terrain. You’ll cover 35 to 43 miles (56 to 69 km) daily , with elevation changes from 1,100 to 4,400 ft (335 to 1,341 m) . Expect hill grades of 4-8% on average, with occasional steeper sections up to 15%. To enjoy this adventure, you should be comfortable riding on a variety of surfaces, including paved roads, cobblestone streets, city streets with vehicle traffic, and country back roads. Vehicle support is available if needed, but being well-prepared will make your experience much more enjoyable. Starting a training program 3 to 6 months ahead is recommended to get ready for the beautiful but challenging Tuscan countryside. For more cycling adventures in Tuscany, click here !

What do I need to bring?

This is a list of clothing & footwear we recommend you bring: Cycling shorts (padded shorts recommended, try them out before the tour) Riding jerseys T-shirts and/or casual shirts (quick-dry) Bathing suit Bike socks and/or sports socks (quick-dry) Dress or casual socks Windbreaker or cool-weather jacket (rainproof and breathable) Light rain jacket or poncho (cheap version is fine—insurance on sunny days!) Bike shoes Riding gloves Underwear (quick-dry) Sweater or fleece Slacks or light jeans (quick-dry, wrinkle resistant) Belt Comfortable walking shoes Sandals Miscellaneous Passport, wallet and ID Waterproof, zip-lock type plastic bag for your valuables Health insurance card Travel insurance card Cash, credit cards and/or travel cheques Electronic chargers (for camera, MP3 player, e-reader, cell phone) Adaptors or convertors First aid kit Insect repellent Antiseptic cream or antibiotic ointment Antihistamine tablets for hay fever Sunscreen and total bloc Throat lozenges or hard sweets Painkillers Band-aids and ‘Second Skin’ for blisters Rehydration salts Multi-vitamins

Group sizes and age requirements

Group sizes and pricing For this guided bike tour in Tuscany, the usual client-to-guide ratio is 6:1. It takes a minimum of 4 people for this tour to operate. The maximum group size is set at 12 participants. A guided bike tour in Tuscany can be arranged for larger groups. Contact us to make arrangements. Min. age requirements If you are older than 18, you’re good to go. Minors younger than 18 may be permitted to join the bike tour on a case-by-case basis, but must be in the presence of a parent or legal guardian. If your group has bikers under the age of 18, contact us prior to booking to make arrangements.

Getting there and meeting location

The starting point of your guided bike tour in Tuscany is Chiusi, Italy. To get there, most people fly into Umbria International Airport (PEG) , Florence Airport (FLR) , or Rome Fiumicino Airport (FCO) . From there, you can take a shuttle service, public transport, or rent a car to reach Chiusi. Once you’re there, you will meet your guide at a predetermined time at the train station in Chiusi. From there, an arranged transfer will take your group to Pienza, which is where you’ll set off on your first bike ride. More details about the meeting location and time will be provided upon booking.

Safety measures and insurance

We highly recommend that you cover all your bases with both medical and travel protection . To make your booking and traveling experience as carefree as possible , simply choose Redpoint—the official 57hours insurance partner! Redpoint tailors their protection packages for adventure travel, offering a comprehensive travel program, even in remote locations. Trip cancellation, natural disasters, pandemic coverage, medical evacuation, primary medical expenses—regardless of the travel interruption that may happen, Redpoint will have you covered. Once your booking is confirmed and your trip is paid in full, you will be offered to purchase Redpoint’s protection. If you need any help or require more information, let us know and we will be happy to help!

TUSCANY | ITALY

Guided Bike Tour in Tuscany: Cycle the Heart of Italy

5.00 ()

Cyclist riding on a road next to vineyards

Cyclist riding past vineyard rows on a sunny day

Cyclists waiting for dinner in a tavern in Castellina in Chianti

Cyclists making their way down a panoramic road in Tuscany

Cyclists on a paved road with the Black Rooster symbol in the background

Cyclists in front of the Black Rooster in Gaiole in Chianti

Cyclists smiling and waving as they bike down a paved road surrounded by a forest

Group cycling downhill on a paved road in Tuscany

From $3,000 ()

Duration

6 days

Season

May through September

Book a call

Intro
Itinerary
Brochure
Guides
Accommodation and food
Reviews
Things to know

All roads may lead to Rome, but the best ones wind through Tuscany. Over six days, we’ll cycle through an ancient landscape of rolling hills, cypress trees, and olive groves, pedaling straight into the heart of Italy’s most celebrated region. Starting in Pienza, we’ll climb to ancient hilltop towns, descend into valleys filled with vineyards, and stop to taste the wines and food that make this region famous. At night, we’ll stay in hotels with stories of their own—like a restored monastery or a castle on a hill. Between the views and the wine, you’ll want to take the long way home.

Adventure highlights

Ride through paradise

Pedal past scenic vineyards, Renaissance towns, and beautiful pastures
Sweet retreats

Historic monasteries and hilltop castles become your home each night
Tuscan flavors

Enjoy fresh cuisine and taste the region’s famed wines

Download itinerary

Itinerary

We meet in Chiusi, Italy and hop on a group transfer to Pienza, a lovely Renaissance town conceived by Pope Pius II—and the starting point of our first ride! We’ll check into our rooms, change into our cycling clothes, and go through bike fitting. If there’s enough time, a warm up ride will take us to Bagno Vignoni, a thermal village located in the Val d’Orcia Artistic, Natural and Cultural Park. The village is famous for its thermal spa, which has been in use since Roman times! In the evening, we’ll enjoy a welcome dinner in a local trattoria where we’ll taste homemade pici pasta.

Meals: Dinner
Cycling: 30.6 km / 19 miles
Elevation: +396 m / +1,300 ft, -396 m / -1,300 ft
Accommodation: Hotel Relais il Chiostro
Today we embark on a loop ride through the UNESCO-listed Val d’Orcia, whose distinctive landscapes of chalk plains and hilltop settlements inspired Renaissance painters like Daccio and Lorenzetti. Our journey begins with a gentle descent from Pienza followed by rolling hills on quiet country roads. We then climb to Castiglione d’Orcia, where a magnificent 13th-century fortress offers sweeping views of the region. Our route then takes us to the Abbey of Sant’Antimo, an ancient monastery where we might hear the monks’ chanting! We continue through the renowned Brunello vineyards to reach Montalcino, where we’ll explore its medieval streets before cycling back to Pienza.

Meals: Breakfast and lunch
Cycling: 69 km / 43 miles
Elevation: +1,319 m / +4,329 ft, -1,319 m / -4,329 ft
Accommodation: Hotel Relais il Chiostro
Our ride begins with a fun descent from Pienza, cycling through the charming villages of Castelmuzio and Trequanda. The route winds through classic Tuscan scenery filled with olive groves, vineyards, and cypress trees. As we enter the Crete Senesi region, the landscape transforms into dramatic chalk cliffs and gullies, featuring distinctive badlands with isolated farmhouses. Our destination is Lucignano, a hilltop village that showcases medieval town planning and is renowned for its olive oil, honey, ceramics, and architectural sandstone.

Meals: Breakfast, lunch, and dinner
Cycling: 59.6 km / 37 miles
Elevation: +1,064 m / +3,491 ft, -1,034 m / -3,392 ft
Accommodation: Castello di Gargonza
We cycle north through southern Tuscany to Castelnuovo Berardenga, which marks the entrance to the Chianti Classico region. Our route passes through the prestigious vineyards of Castello di Bossi and San Felice before reaching the historic Castello di Brolio, where the Ricasoli family created the original Chianti wine blend in the 12th century. We stop for lunch in Gaiole, known for hosting the vintage bicycle race l’Eroica, before continuing to Castellina in Chianti. The town has a unique medieval street, Via delle Volte, which has evolved into a covered passage housing shops and restaurants. Our day concludes with a wine tasting at a Chianti Classico winery.

Meals: Breakfast and dinner
Cycling: 69 km / 43 miles
Elevation: +1,159 m / +3,804 ft, -1,107 m / -3,631 ft
Accommodation: Castellina at Palazzo Squarcialupi
Today we’ll spend the whole day exploring the Tuscan countryside! We begin by cycling past Monteriggioni, a hilltop town whose medieval towers inspired Dante. We continue through rolling hills, vineyards, and sunflower fields to San Gimignano, a medieval town renowned for its fourteen tower-houses built by wealthy families in the 12th century. After exploring San Gimignano’s historic streets and squares, we return to Castellina in Chianti for dinner at a tavern with sweeping views over the valley’s vineyards.

Meals: Breakfast and dinner
Cycling: 58 km / 36 miles
Elevation: +883 m / +2,898 ft, -1,148 m / -3,765 ft
Accommodation: Castellina at Palazzo Squarcialupi
Our final ride takes us through the famed Chianti hills, where vineyards and thick forests create a breathtaking landscape. We bike along a winding panoramic road to reach Radda in Chianti, a town rich in archaeological history. Our route continues towards the medieval city of Siena and its gothic towers. We’ll share a final celebratory lunch on the outskirts of Siena and toast a great cycling adventure before saying our goodbyes at the train station in the mid-afternoon. From here, you can head to your next destination or explore Siena further!

Meals: Breakfast and lunch
Cycling: 55 km / 34 miles
Elevation: +797 m / +2,616 ft, -1,110 m / -3,642 ft

Guided Bike Tour in Tuscany: Cycle the Heart of Italy

Adventure Brochure

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If you have questions or need help with planning a trip, schedule a call with one of our adventure experts.

Meet your guides

5.00

Tommaso Tornaghi

Tommaso is a passionate tour leader with a great passion for cycling, swimming, tennis, and basketball. Currently pursuing studies in sports science and physical education at Rome University, he harmonizes his academic pursuits with a deep love for physical activity. Tommaso’s favorite tours combine cycling and the art of cooking, and no wonder—he also went through special training for pastry making and he’s very passionate about the culinary arts and history.

5.00

Cicloposse

Cicloposse is a bike tour operator based in Tuscany, dedicated to delivering unforgettable cycling experiences and active vacations throughout Italy. With their passion for biking and love for travel, they are committed to providing excellent services while being socially responsible and creating low-impact trips that respect the environment. They pride themselves in working with local people and small businesses, enabling their guests not only to experience the authentic essence of Italy, but also to positively impact communities they visit. Cicloposse offers seamless organization, meticulous attention to detail, and fostering genuine connection with their guests.

Accommodation and food

Accommodation

After a full day of cycling through the stunning Tuscan countryside, we’ll retreat to three exceptional 3- and 4-star hotels. We’ll spend two nights at Relais Il Chiostro di Pienza, a restored 13th-century convent featuring elegantly designed rooms, a seasonal outdoor pool, and a rooftop terrace with panoramic views. Next, we’ll enjoy one night at Castello di Gargonza, a medieval hamlet where we’ll relax in our authentic rural rooms and explore the lush gardens. For our final two nights, we’ll stay at Palazzo Squarcialupi in Castellina in Chianti, which combines luxury with rich heritage, offering comfortable rooms and a wellness center for relaxation.

All three hotels provide a delicious breakfast, as well as on-site restaurants serving authentic Tuscan cuisine for us to savor after our adventures.

Food

Food and wine set the pace of our Tuscan cycling journey. Our mornings will start with delicious hotel breakfasts to fuel the day’s adventures. As we cycle through Italy’s most famous wine region, we’ll pause twice for tastings of renowned local wines. Our shared meals will showcase the best of Tuscan cuisine: expect regional specialties like pecorino cheese, rich ragù, and local olive oil. One evening stands out: we’ll have dinner at a hilltop tavern, where the views of Chianti’s vineyards will compete with what’s on our plates.

5.00 (5 reviews)

Austin Matalon (source: Google Reviews)

This experience was a peak in my life. The bike guides are experienced and made us feel safe and comfortable for our trips, as well as giving us the opportunities to push ourselves harder if we wanted to. The food was unforgettable and the living accommodations were great! I’m so happy I signed up for this trip. Tuscany is beautiful.

Jan Dolliver (source: Google Reviews)

Cicloposse is a first-rate company. Every detail was covered and the attentiveness to our self-guided tour was spot on. We loved the rides through the Tuscany region and thoroughly enjoyed each hotel. Guiliana and family are delightful!

Donal Mackinnon (source: Google Reviews)

I highly recommend this tour. The organisation was outstanding with excellent accommodation and breakfasts. The trip took us through truly stunning landscapes and villages and the e-bikes handled the tough hills easily. We enjoyed the flexibility of stopping along the way for coffee, refreshments and picnics and the info packs provided valuable recommendations and historical context. Communication was excellent and staff extremely friendly and prompt with responding to queries. An unforgettable bucket list experience !

tom macdonald (source: Google Reviews)

It was a great experience . Rides were challenging . accommodation lovely, scenery spectacular , food delicious. Its family run and they are a great friendly family , very adaptive to individuals needs .

Laura Schoor (source: Google Reviews)

Best trip ever.
Guides and owners of the company were A plus plus.
Meals were awesome. Accomodation was comfortable, spacious, clean. Great location. Scenery beautiful. Biking great.

Things to know

Included:
- - Experienced English-speaking guides with extensive knowledge of the area
  - 6-day guided bike tour in Tuscany
  - Accommodation for five nights in superior hotels (double room with ensuite bathrooms)
  - All breakfasts from Day 2 to Day 6
  - Lunch and dinner as indicated in the itinerary
  - Two wine tastings
  - Snacks and drinks along the way
  - All maps, trip notes, and detailed route directions
  - GPS: Offline maps and voice navigation
  - All shuttles and technical assistance
  - Van support
  - All baggage transfers
  - Water bottle
  - Sales taxes
Add-ons
- - Bike rental
  - Single supplement
Not included:
- - Airfare to Italy
  - Train to Chiusi
  - Meals not indicated in the itinerary
  - Beverages
  - Laundry expenses
  - Personal expenses
  - Guide gratuities — optional
  - Travel and medical insurance — optional
This guided bike tour in Tuscany requires a good fitness level and previous cycling experience. You should be comfortable in the saddle for 4 to 6 hours per day and have enough stamina for six consecutive days of cycling through hilly terrain. You’ll cover 35 to 43 miles (56 to 69 km) daily, with elevation changes from 1,100 to 4,400 ft (335 to 1,341 m). Expect hill grades of 4-8% on average, with occasional steeper sections up to 15%.

To enjoy this adventure, you should be comfortable riding on a variety of surfaces, including paved roads, cobblestone streets, city streets with vehicle traffic, and country back roads. Vehicle support is available if needed, but being well-prepared will make your experience much more enjoyable. Starting a training program 3 to 6 months ahead is recommended to get ready for the beautiful but challenging Tuscan countryside.

For more cycling adventures in Tuscany, click here!
This is a list of clothing & footwear we recommend you bring:
- - Cycling shorts (padded shorts recommended, try them out before the tour)
  - Riding jerseys
  - T-shirts and/or casual shirts (quick-dry)
  - Bathing suit
  - Bike socks and/or sports socks (quick-dry)
  - Dress or casual socks
  - Windbreaker or cool-weather jacket (rainproof and breathable)
  - Light rain jacket or poncho (cheap version is fine—insurance on sunny days!)
  - Bike shoes
  - Riding gloves
  - Underwear (quick-dry)
  - Sweater or fleece
  - Slacks or light jeans (quick-dry, wrinkle resistant)
  - Belt
  - Comfortable walking shoes
  - Sandals
Miscellaneous
- - Passport, wallet and ID
  - Waterproof, zip-lock type plastic bag for your valuables
  - Health insurance card
  - Travel insurance card
  - Cash, credit cards and/or travel cheques
  - Electronic chargers (for camera, MP3 player, e-reader, cell phone)
  - Adaptors or convertors
First aid kit
- - Insect repellent
  - Antiseptic cream or antibiotic ointment
  - Antihistamine tablets for hay fever
  - Sunscreen and total bloc
  - Throat lozenges or hard sweets
  - Painkillers
  - Band-aids and ‘Second Skin’ for blisters
  - Rehydration salts
  - Multi-vitamins
Group sizes and pricing
- - For this guided bike tour in Tuscany, the usual client-to-guide ratio is 6:1.
  - It takes a minimum of 4 people for this tour to operate. The maximum group size is set at 12 participants.
A guided bike tour in Tuscany can be arranged for larger groups. Contact us to make arrangements.

Min. age requirements
- - If you are older than 18, you’re good to go.
  - Minors younger than 18 may be permitted to join the bike tour on a case-by-case basis, but must be in the presence of a parent or legal guardian.
If your group has bikers under the age of 18, contact us prior to booking to make arrangements.
The starting point of your guided bike tour in Tuscany is Chiusi, Italy. To get there, most people fly into Umbria International Airport (PEG), Florence Airport (FLR), or Rome Fiumicino Airport (FCO). From there, you can take a shuttle service, public transport, or rent a car to reach Chiusi.

Once you’re there, you will meet your guide at a predetermined time at the train station in Chiusi. From there, an arranged transfer will take your group to Pienza, which is where you’ll set off on your first bike ride.

More details about the meeting location and time will be provided upon booking.
We highly recommend that you cover all your bases with both medical and travel protection. To make your booking and traveling experience as carefree as possible, simply choose Redpoint—the official 57hours insurance partner!

Redpoint tailors their protection packages for adventure travel, offering a comprehensive travel program, even in remote locations. Trip cancellation, natural disasters, pandemic coverage, medical evacuation, primary medical expenses—regardless of the travel interruption that may happen, Redpoint will have you covered.

Once your booking is confirmed and your trip is paid in full, you will be offered to purchase Redpoint’s protection. If you need any help or require more information, let us know and we will be happy to help!
Deposits

You can secure one of the set dates with a 30% deposit upon booking. The remaining 70% of the trip price is to be paid 90 days prior to departure, at the latest.

Cancellations

Booking fees are non-refundable in all cases. During checkout, however, you can choose one of 57hours’ flexibility options:

Basic
- - In case of cancellation within 48 hours after booking, the amount paid is fully refundable.
  - For cancellations 60 or more days before the trip, you are eligible for a 70% refund of the trip price.
  - For cancellations 0-59 days before the trip, there is no refund.
Flexible
- - In case of cancellation within 48 hours after booking, the amount paid is fully refundable.
  - For cancellations 60 or more days before the trip, you are eligible for a full refund of the trip price.
  - For cancellations 30-59 days before the trip, you are eligible for a 50% refund of the trip price.
  - For cancellations 0-29 days before the trip, there is no refund.
Super Flexible
- - In case of cancellation within 48 hours after booking, the amount paid is fully refundable.
  - For cancellations 30 or more days before the trip, you are eligible for a full refund of the trip price.
  - For cancellations 0-29 days before the trip, you are eligible for a 50% refund of the trip price.
57hours partners with Redpoint Travel Protection, offering you a fully integrated program with a single point of contact for all your needs, from emergency services to travel assistance and protection claims. We highly recommend purchasing a comprehensive protection policy from Redpoint, which will protect you both before and during your travels. Before your departure, your investment is protected by the trip cancellation benefit. Once you depart, your policy provides coverage for trip interruption, medical assistance and rescue, baggage loss, trip delay, and more. Once you complete booking with 57hours, we'll create bespoke quote for you (and your group), making sure you're fully protected for the adventure ahead.