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            Cycling Holidays in Tuscany

            We found 3 Holidays in your search for:

            Destinations (81)
            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 (81)
            Types of Cycling / Grades (1)
            Departure Month

            2025

            2026

            2027

            Level of Support

            Join us on two wheels in Tuscany and experience one of the true cycling classics! Cyclists can expect cypress-lined horizons, world-renowned historical treasures and the best Italian food in all the land when they embark on a cycling tour of Tuscany. This really is one of those must-visit destinations that is best explored by bike. You can enjoy this region by either one of our guided or self-guided tours, allowing you to enjoy Tuscany your way. 

            • All Cycling Holidays
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            Select Order Order By
            Self-Guided
            Self-Guided
            Italy

            Classic Tuscany

            Self-Guided Leisure Cycling Holiday

            Duration

            7 days

            Prices from

            £1,195 P.P.
            View Reviews
            7
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            Classic Tuscany

            Self-Guided Leisure Cycling Holiday

            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.

            Start DateEnd DatePrice p.p.
            28/09/202504/10/2025£1,195.00

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

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

            Season 1 – £1335 24 Mar – 16 Jun and 03 Sep – 29 Oct

            Season 2 – £1575 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
            Self-Guided
            Self-Guided
            Italy

            Tuscany - Pisa to Florence

            Self-Guided Leisure Cycling Holiday

            Duration

            8 days

            Prices from

            £1,175 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 Cycling Holiday

            Start DateEnd DatePrice p.p.
            16/09/2025
            Guaranteed
            23/09/2025£1,175.00

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

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

            Season 1 – £1295 24 Mar – 16 Jun and 03 Sep – 29 Oct

            Season 2 – £1485 17 – 30 Jun and 01 – 02 Sep

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

            Season 1 – £1365 29 Mar – 14 Jun and 09 Sep – 26 Oct

            Season 2 – £1565 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
            Guided
            Guided
            Italy

            Tuscany to Rome

            Guided Electric Bike Holiday

            Duration

            8 days

            Prices from

            £2,255 P.P.
            View Reviews
            6
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            Tuscany to Rome

            Guided Electric Bike Holiday

            E-BIKE HOLIDAY

            This holiday has been designed as an e-bike tour allowing you to experience more on two wheels whilst riding with like-minded Skedaddlers. Confident cyclists will enjoy the boost from a battery for those cheeky climbs and longer distances. With less effort required on the bike, you’ll have more energy at the end of the day for off-the-bike activities. Remember to select your e-bike hire when you book your holiday with us.

            Start DateEnd DatePrice p.p.
            * 24/05/2025
            Guaranteed
            31/05/2025£2,255.00
            13/09/2025
            Guaranteed
            20/09/2025£2,255.00
            • 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
            Quote
            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
            Next

            News, Reviews & Stories

            Charging into the sunset: e-bike holiday

            Skedaddle designer Helen Wallis tells us about her experience riding an e-bike through Tuscany...

            Tuscany to Rome: 10 reasons to cycle Italy’s most beautiful route

            Customer Story: *Trinis Take on Tuscany

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