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            Autumn Cycling Holidays and Tours

            We found 104 Holidays in your search for:

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

            2026

            2027

            2028

            Level of Support

            We found 104 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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            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
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            3
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            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 Sep – 08 Sept

            2027 30 Mar – 26 Oct (excluding dates from 08 Jun – 31 Aug)

            Season 1 – £1775 30 Mar – 07 Jun / 09 Sep – 26 Oct

            Season 2 – £2045 01 Sep – 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
            Spain

            Camino Primitivo

            Self-Guided Mountain Bike Holiday

            Duration

            8 days

            Prices from

            £1,265 P.P.
            1
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            3
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            5
            Grade 3 - 4: Moderate/ Challenging
            More Info BOOK NOW

            Camino Primitivo

            Self-Guided Mountain Bike Holiday

            E-MTB HIRE AVAILABLE

            This tour is great fun on a regular mountain bike or an e-mountain bike and you can choose to hire either when you book your tour 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.

            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 05 Apr – 31 Oct

            Season 1 20 – 31 May / 01 – 31 Oct – £1265

            Season 2 05 – 15 Apr / 01 Jun – 30 Sep – £1395

            2027 29 Mar – 31 Oct

            Season 1 29 Mar – 17 Jun / 01 – 31 Oct – £1295

            Season 2 18 Jun – 30 Sep – £1425

            • Pre-trip cider pouring in the old town of Oviedo
            • The sinuous singletrack switchback descent to Las Grandas
            • Remote, wild routes across high mountains passes
            • Descending out of the rugged Cordillera to the fabulous Roman city of Lugo
            • Tasting Galician-style Octopus washed down with a crisp Albarino white
            • Hearing the eerie wail of bagpipes on arrival into the cathedral square in Santiago
            Photo Highlights Dates
            Self-Guided
            Self-Guided
            Italy

            Strade Bianche Explorer

            Self-Guided Gravel Riding Holiday

            Duration

            8 days

            Prices from

            £1,895 P.P.
            View Reviews
            5
            1
            2
            3
            4
            5
            Grade 3-4 : Moderate/Challenging
            More Info BOOK NOW

            Strade Bianche Explorer

            Self-Guided Gravel Riding 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 throughout July and August)

            Season 1 – £1895 29 Mar – 14 Jun and 09 Sep – 26 Oct

            Season 2 – £2095 15 Jun – 30 Jun and 01 – 08 Sep

            2027 30 Mar – 26 Oct (excluding dates throughout July and August)

            Season 1 – £1995 30 Mar – 14 Jun and 09 Sep – 26 Oct

            Season 2 – £2195 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.

            • Riding some of the classic Strade Bianche route of Tuscany as well as lesser-known gravel routes
            • Cycling through the historic wine regions of Tuscany, stopping off for a bit of wine tasting
            • Exploring the region on a mix of terrains
            • Riding the stunning UNESCO heritage region of Val d’Orcia
            • Relaxing in small villages for a coffee with the locals
            • Easing along the rolling hills of the ‘Colli Senesi’
            • Chilling out with a post-ride Chianti or Brunello
            Photo Highlights Dates
            Guided
            Guided
            Italy

            Tuscany - Strade Bianche Explorer

            Guided Gravel Riding Holiday

            Duration

            8 days

            Prices from

            £2,225 P.P.
            View Reviews
            1
            1
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            5
            Grade 3-4 : Moderate/Challenging
            More Info BOOK NOW

            Tuscany - Strade Bianche Explorer

            Guided Gravel Riding Holiday

            Start DateEnd DatePrice p.p.
            20/09/2026
            Last Spaces
            27/09/2026£2,225.00
            24/04/202701/05/2027£2,295.00
            08/05/202715/05/2027£2,295.00
            25/09/202702/10/2027£2,295.00
            • Riding some of the classic Tuscany gravel routes including the Strade Bianche
            • Cycling through the historic wine regions of Tuscany, stopping off for a bit of wine tasting
            • Exploring the region on a mix of terrains
            • Riding the stunning UNESCO heritage region of Val d’Orcia
            • Relaxing in small villages for a coffee with the locals
            • Easing along the rolling hills of the ‘Colli Sienesi’
            • Chilling out with a post-ride Chianti or Brunello
            Photo Highlights Dates
            Guided
            Guided
            Spain

            La Rioja - Ruta del Vino

            Guided Road Cycling Holiday

            Duration

            7 days

            Prices from

            £2,295 P.P.
            View Reviews
            8
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            Grade 3 : Moderate
            More Info BOOK NOW

            La Rioja - Ruta del Vino

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            27/09/2026
            Fully Booked
            03/10/2026£2,295.00
            14/06/202720/06/2027£2,345.00
            16/09/202722/09/2027£2,345.00
            • Staying at the fantastic San Millan de la Cogolla monastery, a World Heritage Site.
            • Cycling high along the limestone cliffs of the Sierra de Cantabria
            • Enjoying the atmospheric, medieval towns of Ezacary and Laguardia
            • Wine tasting in a Riojan bodega (or two!)
            • Cycling through Mediterranean forests, along mountainsides and through endless vineyards
            • Rolling along the Rio Ebro into Logroño for an authentic slice of tapas heaven in Calle Laurel
            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
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            3
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            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
            Guided
            Guided
            Italy

            Coast to Coast - Puglia to Cilento

            Guided Road Cycling Holiday

            Duration

            8 days

            Prices from

            £2,095 P.P.
            View Reviews
            5
            1
            2
            3
            4
            5
            Grade 3 - 4: Moderate/ Challenging
            More Info BOOK NOW

            Coast to Coast - Puglia to Cilento

            Guided Road Cycling Holiday

            Start DateEnd DatePrice p.p.
            27/09/2026
            Fully Booked
            04/10/2026£2,095.00
            17/04/202724/04/2027£2,195.00
            25/04/202702/05/2027£2,195.00
            26/09/202703/10/2027£2,195.00
            • An epic coast to coast journey through southern Italy riding from the Adriatic coast to the Tyrrhenian Sea
            • Exploring the UNESCO World Heritage sites of Alberobello, Matera, Padula and Paestum
            • Losing ourselves in the labyrinthic white washed alleyways of Noci and Tricarico
            • Climbing the hills of little-known Basilicata, to the hill-top villages of Castelmezzano, Calvello and Marsico Vetere
            • Cycling through the Dolomiti Lucane, southern Italy’s lesser-known Dolomites
            • Enjoying the roller-coaster ride along the Cilento Coast from Palinuro to Paestum
            • Sampling southern Italy’s best food and wine
            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
            6
            1
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            3
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            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

            2027 30 Mar – 26 Oct (excluding dates throughout July and August)

            Season 1 – £1355 30 Mar – 14 Jun and 09 Sep – 26 Oct

            Season 2 – £1565 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
            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 Sep – 08 Sep

            2027 30 Mar – 26 Oct (excluding departures from 08 Jun to 31 Aug)

            Season 1 – £1635 30 Mar – 07 Jun / 09 Sep – 26 Oct

            Season 2 – £1875 01 Sep – 08 Sep

            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
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            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
            Everything about the Skedaddle operation was spot-on, great attention to detail both before and during the trip. I was impressed by all things on the trip, quality of food, route briefings, accommodation, maps. I could go on!
            Paul, Land's End to John O'Groats Classic - 16 Days
            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
            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
            Quote
            On 10+ trips with Skedaddle they have always delivered great trips and service. You get what you pay for and Skedaddle are very good at providing well run cycling holidays.
            Rob, Italy - Sardinia Island Flavours
            Next

            News, Reviews & Stories

            View of the Col d'Allos mountain pass in the French Alps

            Customer Story: Cycling Mont Ventoux and Alpe d’Huez

            After a long hiatus, Paul rejoined us on a Skedaddle tour in the French Alps to conquer classic climbs, including cycling Mont Ventoux. Discover his highlights of this epic road cycling trip below. If there was a prize for the longest gap between Saddle Skedaddle holidays, I might just walk away with it. In the ...

            paul streets
            Paul Streets
            August 3, 2026

            Gallovidian Gravel – a New Gravel Scotland Adventure

            Gravel riding in Scotland just got better! Gallovidian Gravel joins Cycling UK’s growing collection of long-distance must-ride routes.   Since launching our gravel holiday range in 2023, we’ve sampled some of the best gravel riding in Scotland, so we were delighted to be involved in helping Cycling UK create a new off-road route in Dumfries and Galloway - 'Galloway Gravel Escape'. Working ...

            Dave Shuttle - UK Product Lead at Saddle Skedaddle
            Dave Shuttle
            July 25, 2026
            Cyclists riding Hartside Pass on the coast to coast cycle route

            Our official guide to the UK C2C – Coast to Coast ride

              The C2C, also known as the Sea to Sea or Coast to Coast, is undoubtedly the UK’s best-loved challenge ride and attracts a vast array of enthusiastic cyclists each year to take on its legendary ups and downs. This rewarding multi-day coast to coast adventure has become somewhat of a rite of passage for us here in the ...

            Amy McKie
            Amy McKie
            July 22, 2026

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