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            Autumn Cycling Holidays and Tours

            We found 105 Holidays in your search for:

            Destinations (82)
            Types of Cycling / Grades (7)
            Departure Month

            2026

            2027

            2028

            Level of Support

            We found 105 Holidays in your search for:

            Select Order Order By
            Destinations (82)
            Types of Cycling / Grades (7)
            Departure Month

            2026

            2027

            2028

            Level of Support

            Looking for Autumn cycling holidays? A late-season bike tour is a great option for anyone looking to escape the intense summer heat in the Northern Hemisphere and eke out the summer cycling fun! 

            Many places in Southern Europe are still basking in glorious sunshine during September and October, with vineyard harvests bringing plenty of seasonal interest! Popular regions include Andalucia, Sardinia and parts of Portugal. Further afield, destinations like Morocco and Peru also offer some fantastic cycling adventures in extraordinary landscapes. 

            Whether you're looking to go cycling in September, fancy one of our guided cycling holidays in October or prefer to go cycling in November, there's plenty to explore! Take a look at our autumn cycling holidays below to get started. Prefer to go ride earlier in the year? Don't miss our spring cycling tour picks and summer cycling suggestions. 

            • All Cycling Holidays
            • Autumn Cycling Tours

            Page 4 of 11

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            Guided
            Guided
            Italy

            Coast to Coast - L'Adriatico al Tirreno

            Guided Road Cycling Holiday

            Duration

            9 days

            Prices from

            £2,695 P.P.
            View Reviews
            10
            1
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            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            Coast to Coast - L'Adriatico al Tirreno

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            16/05/2026
            Guaranteed
            24/05/2026£2,695.00
            12/09/2026
            Guaranteed
            20/09/2026£2,695.00
            • An epic coast to coast journey riding all the way from the Adriatic coast to the Tyrrhenian Sea
            • Cycling through the smallest republic in Europe, San Marino
            • Easing along the rolling Nove Colli hills, the routes of the famous Italian Gran Fondo
            • Visiting historical sites such as the Palazzo Ducale in Orvieto and San Francis Abbey in Assisi
            • Staying in quality accommodation, with fantastically warm hospitality
            • Riding to Gubbio and Assisi, UNESCO World Heritage sites
            Photo Highlights Dates
            Guided
            Guided
            Italy

            Grand Traverse Explorer - South to North

            Guided Road Cycling Holiday

            Duration

            22 days

            Prices from

            £5,495 P.P.
            View Reviews
            5
            1
            2
            3
            4
            5
            Grade 3 - 4: Moderate/ Challenging
            More Info BOOK NOW

            Grand Traverse Explorer - South to North

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            29/08/2026
            Guaranteed
            19/09/2026£5,495.00
            24/04/202715/05/2027£5,655.00
            28/08/202718/09/2027£5,655.00
            • Riding up the backbone of Italy on a stunning route which takes in some of the best road cycling that Italy has to offer
            • Cycling through 10 UNESCO World Heritage sites and 5 National Parks
            • Visiting some of the most important historical and artistic cities in Italy: Lecce, Assisi, Siena, Venice
            • The camaraderie of your fellow cyclists who’ll be joining you on this incredible tour
            • Immersing yourself in Italian culture – meeting the friendly locals, experiencing delicious culinary specialties and tasting the wines of each region
            • Cycling from the most south-easterly point of the heel of Italy up to Venice, having ridden nearly 1,100 miles and climbed almost 22,000 metres!
            Photo Highlights Dates
            Self-Guided
            Self-Guided
            Italy

            Puglia - The Beautiful South

            Self-Guided Road Cycling Holiday

            Duration

            8 days

            Prices from

            £1,695 P.P.
            View Reviews
            2
            1
            2
            3
            4
            5
            Grade 2 : Gentle
            More Info BOOK NOW

            Puglia - The Beautiful South

            Self-Guided Road Cycling Holiday

            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 from 08 Jun – 31 Aug)

            Season 1 – £1695 29 Mar – 07 Jun / 09 Sep – 26 Oct

            Season 2 – £1955 01 Sept – 08 Sept

            • Savouring the deep red wine of the Salento region and the crisp whites of Locorotondo
            • Enjoying the sights of Alberobello, famous for the ‘trulli’
            • Exploring the gnarled olive groves in the countryside of Alberobello
            • Visiting 2 UNESCO heritage sites; Lecce and Alberobello
            • Admiring the Baroque churches of Lecce
            • Enjoying the panoramic coastal road between Santa Maria di Leuca and Otranto
            Photo Highlights Dates
            Self-Guided
            Self-Guided
            Italy

            Tuscany - Pisa to Florence

            Self-Guided Leisure Cycling Holiday

            Duration

            8 days

            Prices from

            £1,295 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

            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.

            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 – £1295 29 Mar – 14 Jun and 09 Sep – 26 Oct

            Season 2 – £1495 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
            Spain

            Basque Country to Andalucia Classic - North to South

            Guided Road Cycling Holiday

            Duration

            16 days

            Prices from

            £3,995 P.P.
            View Reviews
            21
            1
            2
            3
            4
            5
            Grade 4 : Challenging
            More Info BOOK NOW

            Basque Country to Andalucia Classic - North to South

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            27/09/202612/10/2026£3,995.00
            11/04/202726/04/2027£4,095.00
            25/09/202710/10/2027£4,095.00
            • Cycling through the varied beauty of 14 national parks
            • Delicious regional dishes which change from day to day as you traverse the entire country
            • Crossing the granite Guadarrama and Gredos mountain ranges as you move from the north to the south of the country
            • Views over the Straits of Gibraltar to Morocco
            • The beautiful towns of San Sebastian, Guadaloupe and Ronda
            • The satisfaction of arriving in to Tarifa with over 1,000 miles of Spanish roads having passed beneath your wheels
            Photo Highlights Dates
            Self-Guided
            Self-Guided
            Italy

            Puglia

            Self-Guided Leisure Cycling Holiday

            Duration

            8 days

            Prices from

            £1,395 P.P.
            View Reviews
            4
            1
            2
            3
            4
            5
            Grade 2: Gentle
            More Info BOOK NOW

            Puglia

            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.

            Start DateEnd DatePrice p.p.
            28/09/2026
            Guaranteed
            05/10/2026£1,395.00

            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 departures from 08 Jun to 31 Aug)

            Season 1 – £1565 29 Mar – 07 Jun / 09 Sep – 26 Oct

            Season 2 – £1795 01 Sept – 08 Sept

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

            • Cycling through lush landscapes of ancient olive groves and vineyards
            • Exploring the UNESCO World Heritage towns of Matera and Alberobello
            • Discovering the traditional Trulli houses of Puglia
            • Relaxing each evening in comfortable hotels in authentic towns and villages
            • Stopping at beautiful, sandy beaches with turquoise seas
            • Tasting delicious local products, like extra virgin olive oil and Primitivo wine
            Photo Highlights Dates
            Self-Guided
            Self-Guided
            Italy

            Tuscany - Sacred Routes

            Self-Guided Mountain Bike Holiday

            Duration

            8 days

            Prices from

            £1,795 P.P.
            View Reviews
            4
            1
            2
            3
            4
            5
            Grade 3 - 4: Moderate/ Challenging
            More Info BOOK NOW

            Tuscany - Sacred Routes

            Self-Guided Mountain Bike Holiday

            E-MTB HIRE AVAILABLE

            This holiday is great fun on a regular mountain bike or an e-mountain bike and you can choose to hire either when you book your holiday with us! If you’re an experienced rider, you can choose one of our quality e-mountain hire bikes and experience the buzz of a pedal-assisted ride. Select your e-MTB hire when you book a holiday with us. Bear in mind that the pace will be set to riders with a regular mountain 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.

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

            Season 1 – £1795 29 Mar – 14 Jun and 09 Sep – 26 Oct

            Season 2 – £1995 15 Jun – 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.

            • Staying in lovely Tuscan accommodation overlooking stunning landscapes
            • Riding the Montagnola trails, the location of a well-known Sienese MTB race
            • Sampling the best wines of Chianti, Montepulciano and Montalcino
            • Riding down the “Crete Senesi” on a roller coaster ridge ride
            • Enjoying the journey across Tuscany on a variety of terrain
            • Visiting the famous hilltop towns of San Gimignano, Monteriggioni, San Quirico d‘Orcia and Pienza
            Photo Highlights Dates
            Guided
            Guided
            Italy

            Tuscany - Sacred Routes

            Guided Mountain Bike Holiday

            Duration

            7 days

            Prices from

            £2,195 P.P.
            View Reviews
            8
            1
            2
            3
            4
            5
            Grade 3 - 4: Moderate/ Challenging
            More Info BOOK NOW

            Tuscany - Sacred Routes

            Guided Mountain Bike Holiday

            E-MTB HIRE AVAILABLE

            This holiday is great fun on a regular mountain bike or an e-mountain bike and you can choose to hire either when you book your holiday with us! If you’re an experienced rider, you can choose one of our quality e-mountain hire bikes and experience the buzz of a pedal-assisted ride. Select your e-MTB hire when you book a holiday with us. Bear in mind that the pace will be set to riders with a regular mountain bike.

             

            Start DateEnd DatePrice p.p.
            16/05/2026
            Contact Us
            22/05/2026£2,195.00
            05/09/202611/09/2026£2,195.00
            • Staying in lovely Tuscan accommodation overlooking stunning landscapes
            • Riding the Montagnola trails, the location of a well-known Sienese MTB race
            • Sampling the best wines of Chianti, Montepulciano and Montalcino
            • Riding down the Crete Senesi on a roller-coaster ridge ride
            • Enjoying the journey across Tuscany on a variety of terrain
            • Visiting the famous hilltop towns of San Gimignano, Monteriggioni, San Quirico d‘Orcia and Pienza
            Photo Highlights Dates
            Guided
            Guided
            Morocco

            Atlas to Desert

            Guided Cycling Holiday

            Duration

            9 days

            Prices from

            £1,755 P.P.
            View Reviews
            3
            1
            2
            3
            4
            5
            Grades 3 - 4: Moderate/ Active
            More Info BOOK NOW

            Atlas to Desert

            Guided Cycling Holiday

            Start DateEnd DatePrice p.p.
            26/09/202604/10/2026£1,755.00
            03/04/202711/04/2027£1,845.00
            25/09/202703/10/2027£1,845.00
            • Biking across the remote, beautiful, and untouched Jebel Sirwa mountains
            • Exploring crumbling remains of the past in Morocco’s many kasbahs
            • Riding a huge variety of rewarding tracks and trails
            • Sleeping under the stars in the Sahara Desert
            • Relaxing in one of Morocco’s most beautiful palm oases
            • Strolling through the spellbinding network of souks in Marrakech medina
            Photo Highlights Dates
            Self-Guided
            Self-Guided
            Italy

            Classic Tuscany

            Self-Guided Leisure Cycling Holiday

            Duration

            8 days

            Prices from

            £1,495 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.

            Start DateEnd DatePrice p.p.
            25/09/202602/10/2026£1,495.00

            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 – £1695 29 Mar – 14 Jun and 09 Sep – 26 Oct

            Season 2 – £1995 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
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            Not sure which trip's right for you? Just ask!

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

            Quote
            Saddle Skedaddle staff were excellent. Consistently high standards delivered year on year. Don't think I'd trust anybody else when booking a cycling holiday!
            Susan, Slovenia - Capital to Coast, Leisure Cycling Holiday
            Quote
            This was the best of the several organised bike tours I've been on by light years, and I'm now looking at doing other tours with Skedaddle.
            Jay, France - St Malo to Nice, Road Cycling Holiday
            Quote
            One of the very best trips! The kindness and professionalism of the lead guide and his locally based colleagues was outstanding in every respect.
            Brenda, Italy - Dolomites of Brenta, Guided Mountain Bike Holiday
            Quote
            From the first day to the last, everything was fantastic. We never had to worry about anything. Hotels, van pick-ups, guides - you had it all covered!
            Carol and Jim - Peru, Cycling Holiday
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            News, Reviews & Stories

            Mountain Biking Across Sardinia

            The story behind our most popular mountain bike holiday in Italy which has been running for more than 20 years!

            Peru - Positive Impact Fund

            Our long-term partner in Peru has introduced an increidble new scheme to promote responsible travel.

            Meet the Guides: Dave Jones

            Say hi to Dave, UK cycling guide who first joined the scene 14 years ago guiding a mountain bike trip and was instantly hooked.

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