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            Small Group Cycling Holidays

            We found 104 Holidays in your search for:

            Destinations (81)
            Types of Cycling / Grades (7)
            Departure Month

            2025

            2026

            2027

            Level of Support

            We found 104 Holidays in your search for:

            Select Order Order By
            Destinations (81)
            Types of Cycling / Grades (7)
            Departure Month

            2025

            2026

            2027

            Level of Support

            Join a group of likeminded riders on a small group holiday with Skedaddle! Whether you’re looking to join as a couple, group of friends, or as a solo traveller, you’ll feel part of one passionate pedallin’ community. Our tour leaders and guides will be on hand throughout your trip to ensure everything runs smoothly. You’ll also have a dedicated support vehicle to assist with everything from mechanical issues to emergency back-up and extra supplies.

            On a group tour, we take care of all your accommodation and luggage transfers. The only thing you’ll need to focus on is turning the pedals, enjoying the beautiful scenery and wondering what you’ll have for lunch (did we mention the legendary Skedaddle picnics?). It’s no wonder our small group tours are so popular!

            • All Cycling Holidays
            • SMALL GROUP CYCLING HOLIDAYS

            Page 6 of 11

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            Guided
            Guided
            Italy

            Puglia

            Guided Leisure Cycling Holiday

            Duration

            8 days

            Prices from

            £2,095 P.P.
            View Reviews
            12
            1
            2
            3
            4
            5
            Grade 2: Gentle
            More Info BOOK NOW

            Puglia

            Guided Leisure Cycling Holiday

            OPTIONAL E-BIKE DEPARTURES

            We offer this holiday with an e-bike only departure as well as regular trips where you can choose a regular bike or a pedal assist e-bike hire. Our e-bike only departures allow 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. You may choose to hire an e-bike on a regular trip but bear in mind that the pace will be set to riders without an e-bike.

            Start DateEnd DatePrice p.p.
            20/09/2025
            Guaranteed
            27/09/2025£2,095.00
            • Cycling through wonderful landscapes of ancient olive groves, vineyards and stunning coastlines
            • Exploring the UNESCO World Heritage town of Alberobello and the Baroque city of Lecce
            • Discovering the traditional Trulli houses of Puglia
            • Relaxing each night in comfortable 3 and 4* hotels in authentic Apulian towns and villages
            • Stopping at beautiful sandy beaches with turquoise seas
            • Tasting delicious Apulian produce, like orecchiette and extra virgin olive oil
            Photo Highlights Dates
            Guided
            Guided
            United Kingdom

            Cotswolds - Bourton-on-the-Water

            Guided Leisure Cycling Holiday

            Duration

            5 days

            Prices from

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

            Cotswolds - Bourton-on-the-Water

            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.
            16/06/2025
            Last Spaces
            20/06/2025£1,095.00
            • Staying at Harrington House, a comfortable HF Country House in the centre of picturesque Bourton-on-the-Water
            • Three days guided cycling with an experienced leader
            • Enjoying leisurely rides through beautiful rolling countryside
            • Visiting the famous Cotswold market town of Stow-on-the-Wold
            • Visiting the historic village of Bibury, famous for its stone cottages which once housed weavers
            • Cycling through beautiful chocolate box villages
            Photo Highlights Dates
            Guided
            Guided
            United Kingdom

            Lake District - Derwent Water

            Guided Leisure Cycling Holiday

            Duration

            5 days

            Prices from

            £1,045 P.P.
            View Reviews
            7
            1
            2
            3
            4
            5
            Grade 2-3: Gentle/Moderate
            More Info BOOK NOW

            Lake District - Derwent Water

            Guided Leisure Cycling Holiday

            OPTIONAL E-BIKE DEPARTURES

            We offer this holiday with an e-bike only departure as well as regular trips where you can choose a regular bike or a pedal assist e-bike hire. Our e-bike only departures allow 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. You may choose to hire an e-bike on a regular trip but bear in mind that the pace will be set to riders without an e-bike.

            Start DateEnd DatePrice p.p.
            * 14/07/2025
            Guaranteed
            18/07/2025£1,045.00
            22/09/2025 E-Bike Departure26/09/2025£1,045.00
            • Stay at Derwent Bank, Keswick – a comfortable HF Country House sitting directly on the banks of Derwent Water
            • Spin your legs gently along country lanes or challenge them as you climb up towards some Lakeland fells
            • Admire the vista across the lake to Skiddaw and Blencathra
            • Treat yourself to delicious cake pit-stops in charming local cafés
            • Let the lovely Lakeland landscapes inspire your daily cycling
            • Visit Castlerigg Stone Circle – an ancient monument built around 3000 BC
            Photo Highlights Dates
            Guided
            Guided
            United Kingdom

            Derbyshire Dales - Dovedale

            Guided Leisure Cycling Holiday

            Duration

            5 days

            Prices from

            £995 P.P.
            View Reviews
            3
            1
            2
            3
            4
            5
            Grade 2-3: Gentle/Moderate
            More Info BOOK NOW

            Derbyshire Dales - Dovedale

            Guided Leisure Cycling Holiday

            OPTIONAL E-BIKE DEPARTURES

            We offer this holiday with an e-bike only departure as well as regular trips where you can choose a regular bike or a pedal assist e-bike hire. Our e-bike only departures allow 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. You may choose to hire an e-bike on a regular trip but bear in mind that the pace will be set to riders without an e-bike.

            Start DateEnd DatePrice p.p.
            * 04/08/2025
            Guaranteed
            08/08/2025£995.00
            • Stay at Peveril of the Peak, a comfortable HF Country House in the Peak District National Park
            • Relax in the heart of the Derbyshire Dales
            • Flit across the famous stepping stones at scenic Dovedale
            • Follow the Tissington, Manifold and High Peak Trails - miles of peaceful off-road cycling
            • Explore the area using the very railroads that shaped it
            • Cycling through the impressive Manifold valley
            Photo Highlights Dates
            Guided
            Guided
            Spain

            Granada to Seville

            Guided Leisure Cycling Holiday

            Duration

            9 days

            Prices from

            £2,595 P.P.
            View Reviews
            3
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            Granada to Seville

            Guided Leisure Cycling Holiday

            Spain Special

            SAVE £100! Save £100 on our tour departing 27/09/2025. Book before 30 June with the promo code SPAIN25 and your discount will be applied once your booking is confirmed. Ts and Cs apply.

            Start DateEnd DatePrice p.p.
            * 27/09/2025 E-Bike Departure05/10/2025£2,595.00
            • Cycling between 3 of the most magnificent cities in Andalucia
            • Riding through rolling sierras and olive groves
            • Making use of the Vias Verdes
            • Exploring the architectural wonders of Granada
            • Visiting Cordoba – the birth place of Spanish Flamenco
            • Celebrating your trip in the capital of the south, Seville
            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.
            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
            Guided
            Guided
            Italy

            Grand Traverse Explorer - South to North

            Guided Road Cycling Holiday

            Duration

            22 days

            Prices from

            £5,595 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.
            * 23/08/2025
            Guaranteed
            13/09/2025£5,595.00
            25/04/202616/05/2026£5,875.00
            29/08/202619/09/2026£5,875.00
            • 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
            Spain

            La Rioja - Ruta del Vino

            Guided Road Cycling Holiday

            Duration

            7 days

            Prices from

            £2,175 P.P.
            View Reviews
            8
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            La Rioja - Ruta del Vino

            Guided Road Cycling Holiday

            Spain Special

            SAVE £100! Save £100 on our tour departing 21/09/2025. Book before 30 June with the promo code SPAIN25 and your discount will be applied once your booking is confirmed. Ts and Cs apply. 

            Start DateEnd DatePrice p.p.
            * 21/09/202527/09/2025£2,175.00
            • 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
            Japan

            Fuji to Kyoto

            Guided Cycling Holiday

            Duration

            12 days

            Prices from

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

            Fuji to Kyoto

            Guided Cycling Holiday

            Start DateEnd DatePrice p.p.
            09/11/2025
            Fully Booked
            20/11/2025£5,135.00
            23/11/202504/12/2025£5,135.00
            12/04/202623/04/2026£5,755.00
            08/11/202619/11/2026£5,755.00
            • Majestic Mt. Fuji and lovely Lake Kawaguchi
            • Exploring Nagahama and the awesome Hikone Castle
            • Hatage Onsen and its soothing effects after a day’s cycling
            • Bullet Trains and Bento boxes
            • Taking in colourful Kyoto
            • Peaceful pedalling and rural riding
            Photo Highlights Dates
            Guided
            Guided
            Peru

            Andean Journey

            Guided Mountain Bike Holiday

            Duration

            13 days

            Prices from

            £3,295 P.P.
            1
            2
            3
            4
            5
            Grade 3 - 4: Moderate/ Challenging
            More Info BOOK NOW

            Andean Journey

            Guided Mountain Bike Holiday

            Start DateEnd DatePrice p.p.
            04/10/2025
            Guaranteed
            16/10/2025£3,295.00
            16/05/202628/05/2026£3,465.00
            03/10/202615/10/2026£3,465.00
            • Remote wilderness cross-country riding
            • Camping on the high altiplano
            • Fun trails around Lago Langui and the Cañón de Tinajani
            • Exploring the Sacred Valley of the Inca by bike
            • Visiting the Historic Sanctuary of Machu Picchu
            • Homestay on the shores of Lago Titicaca after visiting the Uros floating islands
            Photo Highlights Dates
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            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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