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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

          2025

          2026

          2027

          Level of Support

          We found 3 Holidays in your search for:

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

          2025

          2026

          2027

          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

          $3,335 P.P.
          View Reviews
          6
          1
          2
          3
          4
          5
          Grade 3 : Moderate
          More Info BOOK NOW

          Tuscany to Rome

          Guided Electric Bike Tour

          SAVE ON 2026 ESCAPES

          Save $125 on this holiday when you book before 10 November 2025. Enter promo code BN26 when you book and your discount will be applied after your booking is confirmed. Ts and Cs apply.

          Start DateEnd DatePrice p.p.
          * 23/05/202630/05/2026$3,335.00
          * 12/09/202619/09/2026$3,335.00
          • 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

          $1,950 P.P.
          View Reviews
          5
          1
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          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 – $1950 29 Mar – 14 Jun and 09 Sep – 26 Oct

          Season 2 – $2235 15 – 30 Jun and 01 – 08 Sep

          Alternatively for a great value holiday 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.

          • 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

          7 days

          Prices from

          $1,710 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. You may choose to hire an e-bike on a group or supported tour but bear in mind that the pace will be set to riders without an e-bike.

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

          2025 24 Mar – 29 Oct (excluding dates throughout July and August)

          Season 1 – $1910 24 Mar – 16 Jun and 03 Sep – 29 Oct

          Season 2 – $2250 17 Jun – 30 Jun and 01 – 02 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, Radda in Chianti 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.

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          The services provided by Saddle Skedaddle were excellent from the initial queries, through to the booking of the holiday, and the holiday itself.
          Bruce, The Azores - Islands and Volcanoes
          Quote
          The guides and other group members really made the holiday enjoyable. Our guide was friendly, professional and knowledgeable.
          Elaine, Italy - Via Francigena (Tuscany to Rome)
          Quote
          We had the most amazing holiday. Slovenia was stunning and we kept stopping to take photos as round every bend was another fabulous view.
          Wendy, Slovenia - Highlights of Lake Bled
          Quote
          Couldn't fault the pre-trip information, the helpful staff on the telephone and the accurate description of what to expect.
          Jean, Holland - The Tulip Tour
          Quote
          Everything about the holiday was superb, from the initial contact with Skedaddle through to the very end of the trip. Excellent personal service.
          Jane, UK - Coast to Coast
          Quote
          It was first class from start to finish. Logistics and support including from our local rep were flawless, and accommodation and dining were truly fantastic.
          Robert, Portugal - Port and Wine
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