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            Guaranteed Departures

            We found 19 Guaranteed Departures in your search

            Destinations
            Departure Month

            2025

            2026

            Types Of Cycling

            All Cycling Leisure Cycling Mountain Biking Road Cycling Family Cycling Cycling Adventures Gravel Riding

            We found 19 Guaranteed Departures in your search

            Select Order Order By
            Destinations
            Departure Month

            2025

            2026

            What are ‘Guaranteed Departures’? Our group trips need a minimum number of riders before we can give things the go ahead. Our Guaranteed Departures are trips which have already reached that minimum, meaning you can place a booking and start looking forward to your trip straight away. Browse all upcoming Guaranteed Departures below and click on the ‘Dates’ tab to see all available tour dates for a particular holiday. If the group tour you are looking at is not yet guaranteed, then you can still make a booking and chat to our sales team about how many more riders are needed before it becomes guaranteed.

            Page 2 of 2

            Select Order Order By
            Guided

            Scotland - Tour d'Ecosse

            Guided Road Cycling Holiday

            Guided
            Scotland

            Scotland - Tour d'Ecosse

            Guided Road Cycling Holiday

            Start

            04/07/2026

            Duration

            8 days

            Prices from

            £1,855 P.P.
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW

            SAVE ON 2026 ESCAPES

            Save £100 on this holiday when you book before 31 October 2025. Enter promo code BN26 when you book and your discount will be applied after your booking is confirmed. Ts and Cs apply.

            Start DatePrice p.p.
            * 02/05/2026£1,855.00
            * 23/05/2026£1,855.00
            * 13/06/2026£1,855.00
            * 04/07/2026£1,855.00
            * 08/08/2026£1,855.00
            * 05/09/2026£1,855.00

            Highlighted trips are already guaranteed

            • Quiet single-track roads for miles on end
            • Bealach Na Ba – the greatest road ascent in the UK
            • Feasting on fresh seafood after a day in the saddle
            • Stunning views out over the Isle of Skye
            • Cycling the peaceful lochside roads of Scotland
            • The swooping coastal road from Ullapool to Kinlochewe
            Photo Highlights Dates
            Guided

            Land's End to John O'Groats Explorer

            Guided Road Cycling Holiday

            Guided
            United Kingdom

            Land's End to John O'Groats Explorer

            Guided Road Cycling Holiday

            Start

            11/07/2026

            Duration

            22 days

            Prices from

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

            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 DatePrice p.p.
            09/05/2026£4,895.00
            06/06/2026£4,895.00
            11/07/2026£4,895.00
            05/09/2026£4,895.00

            Highlighted trips are already guaranteed

            • Ride the length of Britain from toe to tip and declare yourself an ‘End to Ender’
            • Experience the regional changes in tradition, culture and accents as you progress from county to county
            • Enjoy spectacular scenery from Cheddar Gorge to the Cairngorms
            • 3 countries in 19 days of riding
            • 1,000 miles of Britain at its best
            • Cornish pasties to haggis and everything in between
            Photo Highlights Dates
            Guided

            Grand Traverse Explorer - South to North

            Guided Road Cycling Holiday

            Guided
            Italy

            Grand Traverse Explorer - South to North

            Guided Road Cycling Holiday

            Start

            29/08/2026

            Duration

            22 days

            Prices from

            £5,495 P.P.
            1
            2
            3
            4
            5
            Grade 3 - 4: Moderate/ Challenging
            More Info BOOK NOW
            Start DatePrice p.p.
            25/04/2026£5,495.00
            29/08/2026£5,495.00

            Highlighted trips are already guaranteed

            • 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

            Land's End to John O'Groats Explorer

            Guided Road Cycling Holiday

            Guided
            United Kingdom

            Land's End to John O'Groats Explorer

            Guided Road Cycling Holiday

            Start

            05/09/2026

            Duration

            22 days

            Prices from

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

            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 DatePrice p.p.
            09/05/2026£4,895.00
            06/06/2026£4,895.00
            11/07/2026£4,895.00
            05/09/2026£4,895.00

            Highlighted trips are already guaranteed

            • Ride the length of Britain from toe to tip and declare yourself an ‘End to Ender’
            • Experience the regional changes in tradition, culture and accents as you progress from county to county
            • Enjoy spectacular scenery from Cheddar Gorge to the Cairngorms
            • 3 countries in 19 days of riding
            • 1,000 miles of Britain at its best
            • Cornish pasties to haggis and everything in between
            Photo Highlights Dates
            Guided

            Bilbao to Santiago

            Guided Road Cycling Holiday

            Guided
            Spain

            Bilbao to Santiago

            Guided Road Cycling Holiday

            Start

            07/09/2026

            Duration

            11 days

            Prices from

            £3,225 P.P.
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW
            Start DatePrice p.p.
            28/06/2026£3,225.00
            07/09/2026£3,225.00

            Highlighted trips are already guaranteed

            • Riding along the stunning and dramatic Cantabrian coastline
            • Enjoying a fabulous seafood platter in San Vicente de Barquera
            • Pouring cider in the old town of Oviedo
            • Arriving at the roof of the ‘Camino Primitivo‘, Puerto Palo
            • Cycling through beautiful, rural, enchanting Galicia to arrive in historical Santiago to collect a pilgrims’ certificate
            • The arrival at ‘the end of the world’ and awesome Cape Finisterre
            Photo Highlights Dates
            Guided

            Bilbao to Barcelona

            Guided Road Cycling Holiday

            Guided
            Spain

            Bilbao to Barcelona

            Guided Road Cycling Holiday

            Start

            24/09/2026

            Duration

            10 days

            Prices from

            £2,945 P.P.
            1
            2
            3
            4
            5
            Grade 3 - 4: Moderate/ Challenging
            More Info BOOK NOW
            Start DatePrice p.p.
            06/05/2026£2,945.00
            03/09/2026£2,945.00
            24/09/2026£2,945.00

            Highlighted trips are already guaranteed

            • An epic coast to coast adventure – riding all the way from the Atlantic to the Med under your own steam
            • Cycling with the impressive back-drop of the Pyrenees by your side
            • Dining each evening on rustic Spanish mountain cuisine
            • The striking pink granite of the Parc Natural de Montserrat
            • Dramatic castles, forts and monasteries perched on every hilltop
            • Seeing Barcelona stretched out in front of you, with the sea beyond
            Photo Highlights Dates
            Guided

            Prague to Venice

            Guided Road Cycling Holiday

            Guided
            Czech Republic, Austria, Slovenia & Italy

            Prague to Venice

            Guided Road Cycling Holiday

            Start

            05/06/2027

            Duration

            21 days

            Prices from

            £5,775 P.P.
            1
            2
            3
            4
            5
            Grade 3 : Moderate
            More Info BOOK NOW
            Start DatePrice p.p.
            06/06/2026£5,775.00
            04/07/2026£5,775.00
            01/08/2026£5,775.00
            05/06/2027£6,195.00
            03/07/2027£6,195.00

            Highlighted trips are already guaranteed

            • A journey from Central Europe to the Mediterranean through four European countries
            • Visit the vibrant capitals of Prague, Vienna and Ljubljana
            • Learn about the historical Central European regions of Bohemia and Styria
            • Explore the UNESCO World Heritage sites of Prague, Cesky Krumlov, Vienna, Graz, and Venice
            • Have a well deserved end-of-ride pilsner seated in the village square of a little Bohemian village
            • Enjoy quiet countryside roads with sweeping views all the way from Prague to Vienna
            • Staying in quality accommodation, with warm traditional hospitality
            • Feast on the traditional dishes, desserts and drinks of the Czech, Austrian and Slovenian cuisine.
            Photo Highlights Dates
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            Useful Holiday Information

            How to plan
            a cycling
            holiday
            Join a group
            or go
            self-guided?
            Choosing Your
            Cycling Holiday Grade
            Guaranteed
            Small Group
            Departures
            What our
            holidays
            include
            Frequently
            Asked
            Questions
            Quote
            After over 40 tours with other operators, I was apprehensive about trying a new company, but have come away extremely pleased with Skedaddle!
            Bruce, Italy - Sardinian Mountains
            Quote
            All queries were replied almost immediately! Well done, Skedaddle, you have provided good consultant, good tour leader and good technical assistant.
            Sin Siew Tag, UK - Land's End to John O'Groats
            Quote
            This trip had something for everybody! The crew were fantastic, they were a vital part of the trip. The rest was the magic of Italy.
            Nigel, Italy - Grand Traverse
            Quote
            A fantastic journey of a lifetime led by excellent guides. Loved the Gorge du Verdon - tremendous climb and stupendous view.
            Miles, France - St Malo to Nice
            Quote
            I was the least experienced in the group - but was made to feel very comfortable and given lots of instruction and help.
            Catharine, France - Le Ventoux a Velo
            Quote
            Quite simply, there are not enough superlatives to describe how beautiful the Tuscan countryside and the accommodation chosen were!
            Robert, Italy - Tuscany Tourer
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