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          Leisure Cycling Tours in Tuscany

          We found 3 Holidays in your search for:

          Destinations (1)
          Types of Cycling / Grades (1)
          Departure Month

          2026

          2027

          2028

          Level of Support

          We found 3 Holidays in your search for:

          Select Order Order By
          Destinations (1)
          Types of Cycling / Grades (1)
          Departure Month

          2026

          2027

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          Level of Support
          All Bike Tours in Tuscany Road Cycling in Tuscany Mountain Biking in Tuscany Gravel Riding in Tuscany Family Cycling in Italy All Cycling Tours in Italy Cycling in Emilia-Romagna Cycling in Sicily Bike and Boat

          Tuscany holds the famous city of Florence, one of Italy’s most beautiful icons, however there is more to Tuscany than just Florence. Tuscany is also home to the Apennine Mountains, famous towns of Siena and San Gimignano and Chianti’s olive groves and vineyards, all of which are perfect for exploring on a leisure cycling vacation.

          Explore our range of leisure tours below to find the tour that suits you and your cycling needs today.

          • All Cycling Holidays
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          • Tuscany Leisure Cycling Tours
          Select Order Order By
          Guided
          Guided
          Italy

          Tuscany to Rome

          Guided Electric Bike Tour

          Duration

          8 days

          Prices from

          $3,425 P.P.
          View Reviews
          7
          1
          2
          3
          4
          5
          Grade 3 : Moderate
          More Info BOOK NOW

          Tuscany to Rome

          Guided Electric Bike Tour

          LAST CHANCE OFFERS!

          Choose half-price bike hire or get 5% off tour departing 12 Sep 2026. Book before 01 June 2026 and enter promo code LETSGO26. Your discount will be applied once your booking is confirmed. Ts and Cs apply.

          Start DateEnd DatePrice p.p.
          23/05/2026
          Fully Booked
          30/05/2026$3,425.00
          * 12/09/202619/09/2026$3,425.00
          • Staying in Tuscan accommodation overlooking stunning landscapes
          • Discovering the amazing towns of Siena, San Quirico and Pienza
          • Sampling the best wines of Chianti, Montepulciano and Montalcino
          • Enjoying the journey from Tuscany to Rome on a variety of terrain, including ancient Roman roads
          • Exploring the lesser-known historical towns of Lazio, such as Sutri with it’s Roman amphitheatre
          • The sense of achievement riding into St Peter’s Square in Rome
          Photo Highlights Dates
          Self-Guided
          Self-Guided
          Italy

          Tuscany - Pisa to Florence

          Self-Guided Leisure Bike Tour

          Duration

          8 days

          Prices from

          $1,850 P.P.
          View Reviews
          5
          1
          2
          3
          4
          5
          Grade 2-3: Gentle/ Moderate
          More Info BOOK NOW

          Tuscany - Pisa to Florence

          Self-Guided Leisure Bike Tour

          Daily departures available. The season prices below are per person and are applicable for all start dates between and inclusive of the stated dates.

          2026 29 Mar – 26 Oct (excluding dates throughout July and August)

          Season 1 – $1850 29 Mar – 14 Jun and 09 Sep – 26 Oct

          Season 2 – $2135 15 – 30 Jun and 01 – 08 Sep

          To ensure you have the best experience possible, we’d recommend travelling in the Spring or in the Autumn. We don’t as standard offer this tour in the hotter, more humid, busier summer months of July and August. If however your dates are set in July or August, please call us for a chat and we’ll do what we can to accommodate you.

          • Riding between two of Italy’s most iconic cities
          • Exploring Pisa, home of the world-famous Piazza dei Miracoli
          • Cycling along quiet country lanes through Tuscan countryside
          • Cycling past fairy tale Renaissance palaces and villas
          • Visiting Vinci, the birthplace of Leonardo da Vinci
          • Spending a free day in Florence, the birthplace of the Renaissance
          Photo Highlights Dates
          Self-Guided
          Self-Guided
          Italy

          Classic Tuscany

          Self-Guided Leisure Bike Tour

          Duration

          8 days

          Prices from

          $2,135 P.P.
          View Reviews
          7
          1
          2
          3
          4
          5
          Grade 3 : Moderate
          More Info BOOK NOW

          Classic Tuscany

          Self-Guided Leisure Bike Tour

          E-BIKE HIRE AVAILABLE

          This tour is well-suited to both regular bikes and pedal assist e-bikes, and you can choose to hire either when you book your tour with us. Confident cyclists will enjoy the boost from a battery for those cheeky climbs, and with less effort required on the bike, you’ll have more energy at the end of the day for off-the-bike activities.

          Start DateEnd DatePrice p.p.
          25/09/202602/10/2026$2,135.00

          Daily departures available. The season prices below are per person and are applicable for all start dates between and inclusive of the stated dates.

          2026 29 Mar – 26 Oct (excluding dates throughout July and August)

          Season 1 – $2425 29 Mar – 14 Jun and 09 Sep – 26 Oct

          Season 2 – $2850 15-30 Jun and 01-08 Sep

          Alternatively for a great value holiday, please select one of our scheduled departures below.

          To ensure you have the best experience possible, we’d recommend travelling in the Spring or in the Autumn. We don’t as standard offer this tour in the hotter, more humid, busier summer months of July and August. If however your dates are set in July or August, please call us for a chat and we’ll do what we can to accommodate you.

          • Staying at Tuscan farms overlooking stunning countryside
          • Visiting the famous towns of Monteriggioni, Buonconvento, Asciano and Siena
          • Riding through wonderful landscapes, wide open fields, cypress-lined hills and vineyards
          • Trying delicious, regional dishes
          • Sampling the best wines of Chianti, Montepulciano and Montalcino
          • Absorbing the atmosphere of San Gimignano – a UNESCO World Heritage Site
          Photo Highlights Dates

          Not sure which trip's right for you? Just ask!

          Get in touch and we'll help you find your perfect trip.

          You might also like...

          All Types of Cycling in Italy All Types of Cycling in Italy
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          Quote
          What one pays for is not having to worry about anything – and Skedaddle does an excellent job taking care of us. We haven’t tried the other tour companies but why bother when Skedaddle is top notch.
          Roger, France - Chateaux of the Loire
          Quote
          The guides and other group members really made the holiday enjoyable. Our guide was friendly, professional and knowledgeable.
          Elaine, Italy - Tuscany to Rome
          Quote
          All the services we received were first class. This was a real holiday and going with Skedaddle took all the stress of booking accommodation from home, route planning and so on, so all we had to do was enjoy the cycling. This has been one of the best holidays in my life.
          Alison, Italy - Sardinia Island Flavours
          Quote
          What do you like most about Skedaddle? Where do I start? The booking process, the hotels, the guides, the lunches, the places they go, the people I meet, the pit stops, the Skedaddle community, reliability, I can put my trust in them to provide a great and memorable experience.
          David, Austria & Italy - La Via Claudia
          Quote
          Skedaddle holidays are always great; you can ride your bike and they pretty much do the rest! Being able to use two wheels as a mode of transport to travel across the country, supported by Skedaddle, just shows the beauty, and power, of bikes. Thank you for making it possible!
          Kate, UK - C2C
          Quote
          We just LOVED the whole thing – route, weather, food, scenery, being outside – it was probably one of the best holidays we have had.
          Inese, Austria - The Danube Cyclepath
          Next

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          Why you'll absolutely love your next cycling holiday in Piedmont, Italy

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          An interview with Lieven about what makes Veneto such a great gravel destination

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