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          Cities and Culture

          We found 62 Holidays in your search for:

          Destinations (75)
          Types of Cycling / Grades (7)
          Departure Month

          2026

          2027

          2028

          Level of Support

          We found 62 Holidays in your search for:

          Select Order Order By
          Destinations (75)
          Types of Cycling / Grades (7)
          Departure Month

          2026

          2027

          2028

          Level of Support

          From the Moorish architecture of Granada and Seville to the ancient wonders of Rome, vibrant culture of Ljubljana and inspiring art in Vienna, there’s so much to experience on these incredible tours of cities and culture. We’ve curated the best itineraries that blend scenic cycling with sight-seeing and cultural experiences. Whether you’re looking for a relaxed e-bike ride or something a little more challenging, we’ve got a tour that’s just right for you.

          • All Cycling Holidays
          • Cities and Culture

          Page 6 of 7

          Select Order Order By
          Guided
          $125 OFF
          Guided
          Spain

          Andalucia - Costa de La Luz and Cadiz Discoverer

          Guided Gravel Riding Tour

          Duration

          8 days

          Prices from

          $3,335 P.P.
          View Reviews
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          Grade 2-3: Gentle/ Moderate
          More Info BOOK NOW

          Andalucia - Costa de La Luz and Cadiz Discoverer

          Guided Gravel Riding Tour

          Start DateEnd DatePrice p.p.
          29/03/2027
          $125 OFF
          05/04/2027$3,335.00
          24/10/2027
          $125 OFF
          31/10/2027$3,335.00
          • Enjoying Andalucia’s extensive network of non-technical, coastal gravel riding
          • Riding cyclepaths, 4×4 tracks, asphalt lanes, earthy singletrack and sandy trails
          • Experiencing vibrant Tarifa; The gateway to 2 continents
          • Discovering the coast of light’s wild and rugged coastline with huge expansive white sand beaches and traditional fishing villages
          • Indulging in delicious local seafood and local wines and sherries
          • Exploring the lanes of fun-loving Cadiz for the best tapas and flamenco
          • Savouring a glass of sherry in a historic bodega within the Sherry Triangle
          Photo Highlights Dates
          Self-Guided
          $95 OFF
          Self-Guided
          Sweden

          Stockholm's Archipelago

          Self-Guided Leisure Bike Tour

          Duration

          7 days

          Prices from

          $2,035 P.P.
          View Reviews
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          Grade 3 : Moderate
          More Info BOOK NOW

          Stockholm's Archipelago

          Self-Guided Leisure Bike Tour

          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.

          The season prices below are per person. Daily departures are available between and inclusive of the stated dates.

          2027 16 May – 12 Sep

          Season 1 $2035 16-29 May and 30 Aug-12 Sep

          Season 2 $2135 21-29 Aug

          Season 3 $2180 30 May-19 Jun

          Season 4 $2280 20 Jun-20 Aug

          • Exploring scenic Stockholm
          • Island hopping by ferry and bike through coastal Sweden
          • Riding forest trails and waterside routes
          • Exploring harbour towns like Vaxholm and Gustavsberg
          • Discovering Sandhamn’s beaches, boats and colourful charm
          • Stopping for fika, lunches and sea views along the way
          • Soaking up the archipelago’s unique mix of nature and culture
          Photo Highlights Dates
          Self-Guided
          Self-Guided
          Italy

          Piedmont - La Strada del Vino

          Self-Guided Road Bike Tour

          Duration

          8 days

          Prices from

          $2,380 P.P.
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          Grade 3: Moderate
          More Info BOOK NOW

          Piedmont - La Strada del Vino

          Self-Guided Road Bike Tour

          Daily departures available between April and October. The season prices below are per person and are applicable for all start dates between and inclusive of the stated dates.

          2027 19 Apr – 15 Oct (no departures in July and August)

          Season 1 – $2380 19 Apr – 14 Jun / 09 Sep – 15 Oct

          Season 2 – $2680 15 – 30 Jun / 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.

          • Cycling through rolling hills terraced with vineyards and quaint medieval villages
          • Capturing beautiful views that stretch as far as the Alps
          • Admiring castle topped villages which lend a historic romantic feel to the area
          • Tasting some of the best wines in Italy in the regions they are produced; Barolo, Barbaresco and Asti
          • Feasting on some of the best regional food in Italy, including truffles, cheeses and hazelnut Gianduia chocolates!
          Photo Highlights Dates
          Guided
          Guided
          Portugal

          Atlantic Escape

          Guided Road Bike Tour

          Duration

          10 days

          Prices from

          $4,135 P.P.
          View Reviews
          11
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          Grade 3: Moderate
          More Info BOOK NOW

          Atlantic Escape

          Guided Road Bike Tour

          Start DateEnd DatePrice p.p.
          01/05/202710/05/2027$4,135.00
          23/10/202701/11/2027$4,135.00
          • Stunning Sintra and its sunsets
          • The lovely fishing village of Nazare
          • Incredible accommodation in 4 star hotels each night
          • Views from the Arrabida mountains
          • Coastal riding and beautiful beaches
          • Reaching mainland Europe’s most southwesterly point by bike!
          Photo Highlights Dates
          Self-Guided
          Self-Guided
          Spain

          Roads of Ronda

          Self-Guided Road Bike Tour

          Duration

          7 days

          Prices from

          $1,565 P.P.
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          Grade 3: Moderate
          More Info BOOK NOW

          Roads of Ronda

          Self-Guided Road Bike Tour

          Daily departures available. The prices below are per person and are applicable for all start dates between and inclusive of the stated dates.

          2026 – $1565 – 01 Mar – 28 Mar / 05 Apr – 30 Apr / 03 May – 30 Jun / 08 Sep – 30 Nov

          • Staying in the quintessentially Spanish town of Ronda
          • Cycling through the rugged, ‘bandit country’ of the Sierra de las Nieves
          • Reaching the top of the stunning Puerto de las Palomas
          • Tasty tapas and sunset sangrias
          • White villages (pueblos blancos) cut into the hillsides
          • Planning your own cycling days based on our route notes and recommendations
          Photo Highlights Dates
          Guided
          Guided
          Spain

          Roads of Ronda

          Guided Road Bike Tour

          Duration

          7 days

          Prices from

          $3,035 P.P.
          View Reviews
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          Grade 3: Moderate
          More Info BOOK NOW

          Roads of Ronda

          Guided Road Bike Tour

          Start DateEnd DatePrice p.p.
          08/11/2026
          Last Spaces
          14/11/2026$3,035.00
          • Staying in the quintessentially Spanish town of Old Ronda
          • Cycling through the rugged, ‘bandit country’ of the Sierra de las Nieves
          • Climbing the 1,200m up ‘The Colossus’
          • The seemingly never-ending descent down to the fine sands of Estepona
          • Taking a refreshing post ride dip in the Med
          • Tasty tapas and sunset sangrias
          Photo Highlights Dates
          Guided
          $300 OFF
          Guided
          Spain

          Ruta de la Plata - Seville to Santiago

          Guided Gravel Riding Tour

          Duration

          16 days

          Prices from

          $7,050 P.P.
          View Reviews
          2
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          Grade 3-4 : Moderate/Chellenging
          More Info BOOK NOW

          Ruta de la Plata - Seville to Santiago

          Guided Gravel Riding Tour

          Start DateEnd DatePrice p.p.
          24/04/2027
          $300 OFF
          09/05/2027$7,050.00
          03/10/2027
          $300 OFF
          18/10/2027$7,050.00
          • Biking through 4 diverse regions and 7 provinces of Spain
          • Delicious, regional cuisine
          • Sampling a diverse range of trails and paths
          • Exploring historic Roman roads and viaducts
          • 1,000km of challenging linear riding through ever changing landscapes
          • Crossing high passes and endless thrilling descents
          • Arriving in the beautiful Santiago de Compostela at the end of our journey
          Photo Highlights Dates
          Self-Guided
          Self-Guided
          United Kingdom

          Coast and Castles (6 days cycling)

          Self-Guided Leisure Bike Tour

          Duration

          7 days

          Prices from

          $1,425 P.P.
          View Reviews
          4
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          Grade 2-3: Gentle/ Moderate
          More Info BOOK NOW

          Coast and Castles (6 days cycling)

          Self-Guided Leisure Bike Tour

          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.
          26/05/202701/06/2027$1,425.00
          30/06/202706/07/2027$1,425.00
          11/08/202717/08/2027$1,425.00
          01/09/202707/09/2027$1,425.00

          Daily departures available from April to end of September. Call and chat to us if you‘re interested in doing this holiday in October.

          Choose your own dates from:

          2027 $1750 per person

          You can make a booking online or over the phone. Once we have your details, we’ll be able to check availability.

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

          • Cycling past the dramatic Tynemouth Priory
          • Miles of pristine dunes and sandy beaches at Druridge Bay
          • Stunning vistas as you approach imposing Bamburgh Castle
          • Your first glimpse of Edinburgh from the Moorfoot hills
          • The rugged beauty of the borders
          • A celebratory dram in the shadow of Arthur’s Seat
          • Flexibility to choose your own start date
          Photo Highlights Dates
          Supported
          Supported
          United Kingdom

          Coast and Castles

          Supported Leisure Bike Tour

          Duration

          6 days

          Prices from

          $1,625 P.P.
          View Reviews
          3
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          Grade 3-4 : Moderate/Active
          More Info BOOK NOW

          Coast and Castles

          Supported Leisure Bike Tour

          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.
          02/06/202707/06/2027$1,625.00
          15/09/202720/09/2027$1,625.00
          • Following the Tyne past the dramatic Tynemouth Priory
          • Cycling past the pristine dunes and sandy beaches at Druridge Bay
          • Stunning vistas as we approach imposing Bamburgh Castle
          • The rugged beauty of the Scottish Borders
          • Glimpsing Edinburgh as we cycle from the Moorfoot Hills
          • Enjoying an overnight stay in Scotland’s legendary capital
          Photo Highlights Dates
          Self-Guided
          Self-Guided
          United Kingdom

          Coast and Castles (4 days cycling)

          Self-Guided Leisure Bike Tour

          Duration

          5 days

          Prices from

          $760 P.P.
          View Reviews
          1
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          Grade 3-4 : Moderate/Active
          More Info BOOK NOW

          Coast and Castles (4 days cycling)

          Self-Guided Leisure Bike Tour

          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.
          28/05/202701/06/2027$1,090.00
          02/07/202706/07/2027$1,090.00
          13/08/202717/08/2027$760.00
          03/09/202707/09/2027$1,090.00

          Daily departures available from April to end of September, call and chat to us if you‘re interested in doing this holiday in October.

          Choose your own dates from:

          2027 $1410 per person

          You can either make a booking online or over the phone. Once we have your details, we’ll be able to check availability.

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

          • Cycling past the dramatic Tynemouth Priory
          • Miles of pristine dunes and sandy beaches at Druridge Bay
          • Stunning vistas as you approach imposing Bamburgh Castle
          • Your first glimpse of Edinburgh from the Moorfoot hills
          • The rugged beauty of the borders
          • Flexibility to choose your own start date or one of our great value scheduled departure dates
          • A celebratory dram in the shadow of Arthur’s Seat
          Photo Highlights Dates
          • Previous page
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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
          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

          Cyclists riding in Sweden on the Coastal Kattegattleden cycle route

          6 Reasons To Cycle In Sweden

          Our holidays in Sweden are some of the most popular in our leisure cycling range. We're excited to introduce a brand new guided group holiday for 2027 cycling the Kattegattleden, Sweden's first national cycle path. Read on to learn more about our tours and six reasons why you'll love cycling in Sweden. Coastal Kattegattleden The 8-day ...

          Paul Snedker
          Paul Snedker
          October 15, 2026
          Scallop shell milestone marker on the Camino de Santiago

          Cycle the Camino de Santiago: Everything you need to know

          If you're planning to cycle the Camino de Santiago, you're in for one of the most inspiring linear journeys on the planet. The world-renowned Camino de Santiago has captivated pilgrims and adventurers for centuries. At Skedaddle, we believe pedalling this popular pilgrimage is a unique way to soak up this ancient corner of Spain. Few ...

          Dan Hirst, Head of Skedaddle Espana
          Dan Hirst
          August 31, 2026

          7 things you’ll love about your cycling holiday in Italy…

          With over cycling holidays (and counting) brought to you by our passionate Skedaddle Italia team, Italy is a world-class destination where we are always excited for folk to explore on two wheels! Always eager to share our local knowledge, we caught up with Naomi, who heads up our team out in Italy. Here are just ...

          Naomi Lindfield
          July 1, 2026

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