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La vita è bella (life is beautiful) here in Tuscany. Instead of just admiring its beauty through your screens, you could be here in Italy soon, thinking to yourself “Am I actually here right now?” You’re just a few clicks away from booking your dream vacation—a week-long, self-guided bike tour through the heart of Tuscany. Verdant vineyard hills, medieval hilltop towns, cypress-lined roads, it all feels like stepping into a postcard. The villas and hotels you’ll stay at are simply marvelous, the food is delicious, and the wine is as crisp and refreshing as it gets. Time to start looking up flights.

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  • Wallpaper-worthy scenes

    Wherever you turn, it will look like the most perfect sight you’ve ever seen

  • Italy’s most beautiful medieval city

    Discover the spectacular Siena, a city encircled by a 1,000-year-old wall and a UNESCO-listed center

  • Heaven for your taste buds

    Italian food needs no introduction—pair it with a glass of Aperol Spritz or Tuscany’s rich red wines

Itinerary

A self-guided bike tour through the heart of Tuscany might just be the best way to experience this wonder of a region. You’ll be riding through its spectacular landscapes for a week, experiencing everything from lush vineyards and olive orchards to lovely cobblestone streets and vibrant cities. Your guides organized terrific lodgings as well as baggage transfers, breakfast, detailed routes, and the best local recommendations. For a carefree holiday, it doesn’t get much better than this—explore Tuscany at your own pace and with your own people.

  • Make your way to Pienza, a wonderful renaissance town in Tuscany. Pienza is a remarkable example of renaissance architecture and it’s truly a treat to just stroll around its cobblestone streets. After the bike fitting, go for an optional short test ride to Montepulciano. Retreat to your charming hotel.

    Accommodation: Hotel Relais Il Chiostro di Pienza
    Distance: 35 km / 22 miles

    Pienza in Tuscany
  • Start your day with a long descent down rolling green pastures of the Val d’Orcia to Bagno Vignoni, an ancient village in the heart of Tuscany. Thanks to Via Francigena, an old route which pilgrims once used during antiquity to get to Rome, the thermal waters of Bagno Vignoni have been enjoyed since Roman times. Here you’ll find the Square of Sources, a tank containing water coming from the underground aquifer.

    Along the way you’ll face the challenging uphill to Castiglione d’Orcia, with the imposing Rocca di Tentennano fortress. After a quick break, enjoy a long and flowy downhill to the Romanesque abbey of Sant’Antimo that dates back to the time of Charlemagne—maybe have a coffee or a lunch break. For your last effort of the day, climb a gentle uphill to Montalcino, an Etruscan village and hilltown famous for the Brunello wine. Return to your accommodation in Pienza.

    Accommodation: Hotel Relais Il Chiostro di Pienza
    Distance: 70.6 km / 44 miles
    Elevation: +1,391 m / +4,564 ft | -1,396 m / -4,580 ft
    Optional: Longer ride to San Filippo (100 km / 62 miles)

    Vineyards of Tuscany near Montalcino
  • Today you’ll witness the typical postcard scenery of Tuscany, Italy’s favorite region. Following a picturesque road, ride by Castelmuzio and Trequanda. Afterwards, travel through the fascinating area called La Crete, where you’ll find the traditional Tuscan landscapes of rolling hills, cypress trees, and lone farmhouses. Verdant hills also give way to little domes of clay and you’ll come across almost lunar landscapes of chalk cliffs and gullies.

    Continue cycling and reach Lucignano, a small village that’s a prime example of medieval urban planning due to its system of elliptical rings, still intact. Final destination is the Castello di Gargonza, a magical castle surrounded by lush woods. Dinner today is included.

    Accommodation: Castello di Gargonza
    Distance: 56 km / 35 miles
    Elevation: +978 m / +3,209 ft | -951 m / -3,120 ft
    Optional: Longer ride via Asciano

    Lucignano elliptical shape
  • Pedaling north, whisk past a pair of typical southern Tuscany towns and make a stop at Castelnuovo Berardenga, the gate to Chianti Classico region. Pass through countless vineyards and continue down to Castello di Brolio winery, home of Barone Ricasoli and its world-renowned wine.

    After a few more miles, you’ll get to Gaiole. Stop here for a light lunch. Then it’s time to face the climb to Badia a Coltibuono—when it gets difficult, think of the beautiful downhill to Radda in Chianti that you’ll enjoy! Then it’s the last 10 km up and down to get to your palazzo hotel with a spa.

    Accommodation: Hotel Palazzo Squarcialupi Castellina in Chianti
    Distance: 64.3 km / 40 miles
    Elevation: +1,156 m / +3,793 ft | -1,102 m / -3,615 ft
    Optional: Longer ride to Monte Luco

    Chianti landscapes in Tuscany
  • By pedaling to San Gimignano, you’ll pass by countless vineyards. After going by San Donato in Poggio, Tavarnelle in Val di Pesa, and Barberino, you’ll be in the Florentine Chianti. Soft, colorful, and rolling hills of vineyards and sunflowers provide the perfect backdrop to pre-Roman Etruscan remnants.

    Along the way, you’ll see San Gimignano’s “medieval skyscrapers” in the distance. You’ll have plenty of time to wander through cobblestoned streets, window shop, and buy some Tuscan souvenirs to take home. To get back to Castellina in Chianti, get ready for a beautiful uphill from Poggibonsi.

    Accommodation: Hotel Palazzo Squarcialupi Castellina in Chianti
    Distance: 76 km / 47.5 miles
    Elevation: +1,236 m / +4,055 ft | -1,236 m / -4,055 ft

    San Gimignano old town photographed from above during golden hour
  • Start your day with a long downhill to Monteriggioni, a beautiful town completely walled in! Only 80 people reside within the picture-perfect round turreted walks that crown the hilltop. After passing Casole d’Elsa, continue pedaling through the vineyards and finally arrive in Siena!

    Siena is a medieval city with beautifully preserved Gothic architecture. The entice city was built around the Piazza del Campo, and here you’ll have enough time to shop while exploring many hidden medieval walkways. Go visit the shell-shaped square where the Palio horse race is run and enjoy a glass of Tuscan wine at sunset.

    Accommodation: Hotel STR in Siena
    Distance: 73 km / 45.6 miles
    Elevation: +1,068 m / +3,504 ft | -1,294 m / -4,245 ft

    Piazza del Campo in Siena
  • After breakfast at your final hotel, the tour comes to an end. Leave your rental bikes, catch a flight, or continue your journey!

    Siena town walled in
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Meet your guide

Cicloposse
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

5.00 (3 reviews)
Robert T (source: Guide’s website)

I wanted to thank you all for the wonderful self-guided bike tour my wife and I did 2 weeks ago. I loved every second of it. The bikes were incredible and the directions were so easy to follow. The routes were great and the hotels were amazing. We look forward to riding with Cicloposse again next year.

Jodie Kennedy (source: Guide’s website)

What an amazing week of biking, food, great people & wonderful accommodation you organized for us. Loved every km of the cycling, scenery, towns & scrumptious food & wine at the end of the day. It has been an absolute pleasure dealing with you. Your friend Robert drove us to Florence airport, so we got to ride on the last morning as well. Oh, that vintage bike shop in Gaiole was fantastic & they ship to Australia – bonus! Take care.

David & Marykate (source: Guide’s website)

Ciao! You did great! We had a wonderful time on our trip. The Tuscany Challenge itineraries and routes were well laid out (with some great climbs and descents) and mostly easy to follow (my only suggestion would be more specific directions to the hotels once you arrive at the larger towns). The scenery, of course, was spectacular, and varied, giving us a real sense of the Tuscan countryside and its fascinating, charming villages. All of the hotels were excellent as were the recommended restaurants that we tried. The bikes were top-notch, with only one very minor mechanical issue (incorrectly calibrated computer and broken mount) which Gigi quickly and efficiently fixed. Gigi, in fact, was terrific in every way: personable, knowledgeable and caring – a joy to work with. We would definitely choose Cicloposse again. Molto grazie!

Things to know

  • What you get on this adventure:

      • 7-day self-guided bike tour in Tuscany
      • Accommodation for six nights in excellent hotels, villas, and castles
      • Six breakfasts (special dietary requirements can be accommodated)
      • One gourmet dinner
      • All baggage transfers
      • Route notes, maps, elevation gain and city map
      • RidewithGPS App — navigation offline
      • Sightseeing, restaurant and shopping suggestions
      • Delivery bikes at Pienza hotel & bike fitting
      • Pick-up of bikes and gear in Siena
      • Keepsake Cicloposse water bottle
      • Sales taxes

    What’s not included:

      • Transportation to Italy
      • Lunches and dinners (though you’ll get the best local recommendations)
      • Bikes — available to rent, price per person for the entire tour
        • Grave, race,l or e-bike — $275
        • Hybrid bike — $195
      • Travel and medical insurance — optional
  • To join this self-guided bike tour in Tuscany, you have to be in great shape. There are lots of hilly areas and climbs on this trip and you have to be able to cover these distances. You’ll be cycling 5 or 6 days in a row, covering anywhere between 35-76 km (22-47.5 miles), though you can extend your daily trips. Elevation gains and distances are noted day-by-day in the itinerary above, but you can expect climbing up to 1,391 m (4,564 ft) per day.

  • 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
  • Yes! If you’d like to skip the hassle of bringing a bike for your Tuscany bicycle tour, your guides offer bike rental. Prices are per person and for the entire week of cycling:

      • Hybrid bike — $195
      • Gravel, race, or e-bike — $275
  • A self-guided tour is an independent exploration without a formal guide leading the way. Instead of being part of a group with a tour leader, you will navigate the tour yourself, using resources provided by the operator, such as maps, guidebooks, audio guides, or digital apps.

    For this cycling tour in Italy, your guide will arrange terrific accommodation for you with six breakfasts. All your baggage will be transferred from one accommodation to the next. You’ll get detailed route notes, maps, daily elevation gains and distances, and a city map. For navigation offline, you’ll use the RidewithGPS app.

    Another great thing about going self-guided cycling in Tuscany is that your local guide will provide you with all the sightseeing, restaurant, and shopping suggestions you could imagine! This way you can be sure you’re truly getting the authentic Tuscan experience.

  • Group sizes and pricing

      • It takes a minimum of 2 people for this self-guided bike tour in Tuscany to operate.
      • The maximum group size is set at 16 people.

    Self-guided bike tours 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 older than 16 may be permitted to join the self-guided bike tour in Tuscany on a case-by-case basis, but must be in the presence of a parent or legal guardian.

    If your group has hikers under the age of 18, contact us prior to booking to make arrangements.

  • To get to your self-guided bike tour in Tuscany, the nearest airports are Rome Fiumicino (FCO) and Florence Airport (FLR). It’s up to you whether you’d like to rent a car to reach Pienza, the starting point of your tour, or you’d like to use public transport. Driving with a car takes between 1.5-2.5 hours to Pienza, depending on where you land.

    For the public transport option, after landing you have to reach Chiusi. The easiest option would probably be to take the train. Once in Chiusi, you can take a bus or a taxi to Pienza, the starting point of your self-guided bike tour in Tuscany.

  • We highly recommend that you cover all your bases with both emergency medical and travel insurance.

    With medical insurance, if you have an accident or medical emergency on or off the mountain, you’ll avoid paying out of pocket for costly expenses. This covers everything from hospital treatments to emergency air transportation and more. Travel insurance covers canceled flights, natural disasters and other scenarios that may interrupt your travel plans.

    We also expect you to respect local regulations and take measures to protect yourselves, your guides, and the communities you’re traveling to. If you need assistance selecting the right insurance for your group, let us know and we will be happy to help!

  • A 30% deposit to secure your place is due upon booking. The remaining amount is paid 3 months (90 days) prior to departure. Once the trip is confirmed by the guide, the cancellation policy stated below applies.

      • If Client cancels the Booking anytime prior to thirty (30) calendar days in advance of the trip, Client is entitled to a refund in the amount of fifty percent (50%) of the total amount paid when Booking.
      • After that deadline, Client is not entitled to any refund.
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