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          Guaranteed Departures

          We found 42 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 42 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 tour. 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 4 of 4

          Select Order Order By
          Guided

          Grand Traverse Explorer - South to North

          Guided Road Bike Tour

          Guided
          Italy

          Grand Traverse Explorer - South to North

          Guided Road Bike Tour

          Start

          29/08/2026

          Duration

          22 days

          Prices from

          $7,850 P.P.
          1
          2
          3
          4
          5
          Grade 3 - 4: Moderate/ Challenging
          More Info BOOK NOW
          Start DatePrice p.p.
          25/04/2026$7,850.00
          29/08/2026$7,850.00

          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 Bike Tour

          Guided
          United Kingdom

          Land's End to John O'Groats Explorer

          Guided Road Bike Tour

          Start

          05/09/2026

          Duration

          22 days

          Prices from

          $6,995 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$6,995.00
          06/06/2026$6,995.00
          11/07/2026$6,995.00
          05/09/2026$6,995.00

          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 Bike Tour

          Guided
          Spain

          Bilbao to Santiago

          Guided Road Bike Tour

          Start

          07/09/2026

          Duration

          11 days

          Prices from

          $4,610 P.P.
          1
          2
          3
          4
          5
          Grade 3: Moderate
          More Info BOOK NOW
          Start DatePrice p.p.
          28/06/2026$4,610.00
          07/09/2026$4,610.00

          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
          Bike and Boat

          Venetian Waterways (Venice to Mantova)

          Bike and Barge Tour

          Bike and Boat
          Italy

          Venetian Waterways (Venice to Mantova)

          Bike and Barge Tour

          Start

          12/09/2026

          Duration

          8 days

          Prices from

          $1,995 P.P.
          1
          2
          3
          4
          5
          Grade 1-2 : Easy/Gentle
          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.

          Start DatePrice p.p.
          28/03/2026 Ave Maria$1,995.00
          04/04/2026 Vita Pugna$2,510.00
          11/04/2026 Ave Maria$3,180.00
          18/04/2026 Vita Pugna$2,510.00
          25/04/2026 Ave Maria$3,180.00
          02/05/2026 Vita Pugna$2,695.00
          09/05/2026 Ave Maria$3,510.00
          16/05/2026 Vita Pugna$2,695.00
          23/05/2026 Ave Maria$3,510.00
          30/05/2026 Vita Pugna$2,510.00
          06/06/2026 Ave Maria$3,180.00
          13/06/2026 Vita Pugna$2,510.00
          20/06/2026 Ave Maria$3,180.00
          27/06/2026 Vita Pugna$2,335.00
          04/07/2026 Ave Maria$2,650.00
          11/07/2026 Vita Pugna$2,335.00
          18/07/2026 Ave Maria$2,650.00
          25/07/2026 Vita Pugna$2,335.00
          01/08/2026 Ave Maria$2,650.00
          08/08/2026 Vita Pugna$2,335.00
          15/08/2026 Ave Maria$2,650.00
          22/08/2026 Vita Pugna$2,335.00
          29/08/2026 Ave Maria$3,710.00
          05/09/2026 Vita Pugna$2,850.00
          12/09/2026 Ave Maria$3,710.00
          19/09/2026 Vita Pugna$2,850.00
          26/09/2026 Ave Maria$3,710.00
          03/10/2026 Vita Pugna$2,850.00
          10/10/2026 Ave Maria$3,710.00
          17/10/2026 Vita Pugna$2,510.00
          24/10/2026 Ave Maria$3,180.00

          Highlighted trips are already guaranteed

          • Cycling through some of Northern Italy’s most enticing cities
          • Staying on board the modern, bright and spacious Ave Maria or the traditional Vita Pugna
          • Exploring the beautiful city of Venice
          • Riding alongside the River Po, the longest river in Italy
          • Experiencing the Po Delta, one of Europe’s largest wetlands
          • Spending the day discovering Mantova
          Photo Highlights Dates
          Guided

          Bilbao to Barcelona

          Guided Road Bike Tour

          Guided
          Spain

          Bilbao to Barcelona

          Guided Road Bike Tour

          Start

          24/09/2026

          Duration

          10 days

          Prices from

          $4,210 P.P.
          1
          2
          3
          4
          5
          Grade 3 - 4: Moderate/ Challenging
          More Info BOOK NOW
          Start DatePrice p.p.
          06/05/2026$4,210.00
          03/09/2026$4,210.00
          24/09/2026$4,210.00

          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 Bike Tour

          Guided
          Czech Republic, Austria, Slovenia & Italy

          Prague to Venice

          Guided Road Bike Tour

          Start

          05/06/2027

          Duration

          21 days

          Prices from

          $8,250 P.P.
          1
          2
          3
          4
          5
          Grade 3: Moderate
          More Info BOOK NOW
          Start DatePrice p.p.
          06/06/2026$8,250.00
          04/07/2026$8,250.00
          01/08/2026$8,250.00
          05/06/2027$8,850.00
          03/07/2027$8,850.00

          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

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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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