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Guided Bike Tour in Tuscany: Cycle the Heart of Italy

Itinerary
Guided Bike Tour in Tuscany: Cycle the Heart of Italy
Guide(s)
Tommaso Tornaghi, Cicloposse
Trip options

Add-ons

If you’d like some more privacy, you can choose to pay the single supplement fee here.

If you don’t want to bring your own bike to Tuscany, your guides offer a range of high-quality rental bikes. Select your preferred bike below; prices are for the full trip duration.

All meals indicated in the itinerary are included in the price of this trip. Special dietary requirements can be accommodated, please let us know down below if you have any.

Select a cancellation policy

Things come up, and sometimes plans need to be changed. Check out our flexible cancellation options.
57hours flexibility options
Deposits

When booking a trip, you can either pay for it in full or reserve your spot with a 30% deposit. The remaining 70% of the trip price is to be paid 90 days prior to departure, at the latest.

Cancellations

After 48 hours, booking fees are non-refundable in all cases. You can choose one of 57hours’ flexibility options:

Basic
  • If canceled within 48 hours of booking, a full refund will be issued.
  • If canceled 60 or more days before departure, a 70% refund of the total trip price will be issued.
  • If canceled within 59 days of departure, no refund will be issued.
  • Booking fees are non-refundable after a 48-hour grace period.
Flexible
  • If canceled within 48 hours of booking, a full refund will be issued.
  • If canceled 60 or more days before departure, a full refund of the total trip price will be issued.
  • If canceled 30-59 days before departure, a 50% refund of the total trip price will be issued.
  • If canceled within 29 days of departure, no refund will be issued.
  • Booking fees are non-refundable after 48 hours grace period.
Super Flexible
  • If canceled within 48 hours of booking, a full refund will be issued.
  • If canceled 30 or more days before departure, a full refund of the total trip price will be issued.
  • If canceled within 29 days of departure, a 50% refund of the total trip price will be issued.
  • Booking fees are non-refundable after 48 hours grace period.
Guided Bike Tour in Tuscany: Cycle the Heart of Italy
Itinerary
Guided Bike Tour in Tuscany: Cycle the Heart of Italy
People
1 Person
Date(s)
--
Duration
6 day
Guide(s)
Tommaso Tornaghi, Cicloposse
Reserve deposit (30%) $0
Second Payment Amount: $0

    • 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

      Group cycling downhill on a paved road in Tuscany

    • 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

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

    • 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

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

    • 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

      Cyclists in front of the Black Rooster in Gaiole in Chianti

    • 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

      Cyclists waiting for dinner in a tavern in Castellina in Chianti

    • 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

      Cyclists making their way down a panoramic road in Tuscany

    • 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!

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