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          Cities and Culture

          We found 60 Holidays in your search for:

          Destinations (72)
          Types of Cycling / Grades (7)
          Departure Month

          2025

          2026

          2027

          Level of Support

          We found 60 Holidays in your search for:

          Select Order Order By
          Destinations (72)
          Types of Cycling / Grades (7)
          Departure Month

          2025

          2026

          2027

          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 2 of 6

          Select Order Order By
          Guided
          Guided
          Spain

          Bilbao to Barcelona

          Guided Road Bike Tour

          Duration

          10 days

          Prices from

          $4,210 P.P.
          View Reviews
          2
          1
          2
          3
          4
          5
          Grade 3 - 4: Moderate/ Challenging
          More Info BOOK NOW

          Bilbao to Barcelona

          Guided Road Bike Tour

          Start DateEnd DatePrice p.p.
          06/05/2026
          Fully Booked
          15/05/2026$4,210.00
          03/09/202612/09/2026$4,210.00
          24/09/202603/10/2026$4,210.00
          • 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
          Guided
          Italy

          Puglia

          Guided Bike Tour

          Duration

          8 days

          Prices from

          $3,135 P.P.
          View Reviews
          12
          1
          2
          3
          4
          5
          Grade 2 : Gentle
          More Info BOOK NOW

          Puglia

          Guided 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. 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.
          07/06/202614/06/2026$3,135.00
          20/09/202627/09/2026$3,135.00
          • 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
          Self-Guided
          Self-Guided
          Italy

          Puglia

          Self-Guided Leisure Bike Tour

          Duration

          8 days

          Prices from

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

          Puglia

          Self-Guided Leisure Bike Tour

          SAVE ON 2026 ESCAPES

          Save $85 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.

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

          2025 24 Mar – 29 Oct (excluding departures from 09 Jun to 31 Aug)

          Season 1 – $2135 24 Mar – 08 Jun / 09 Sep – 29 Oct

          Season 2 – $2395 01 Sept – 08 Sept

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

          SAVE ON 2026 ESCAPES

          Save $85 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.

          • Cycling through lush landscapes of ancient olive groves and vineyards
          • Exploring the UNESCO World Heritage town of 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
          Guided
          Guided
          Morocco

          Atlas to Desert

          Guided Bike Tour

          Duration

          9 days

          Prices from

          $2,365 P.P.
          View Reviews
          10
          1
          2
          3
          4
          5
          Grades 3 - 4
          More Info BOOK NOW

          Atlas to Desert

          Guided Bike Tour

          SAVE ON 2026 ESCAPES

          Save $125 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 DateEnd DatePrice p.p.
          25/10/2025
          Guaranteed
          02/11/2025$2,365.00
          * 04/04/202612/04/2026$2,510.00
          * 26/09/202604/10/2026$2,510.00
          03/04/202711/04/2027$2,635.00
          25/09/202703/10/2027$2,635.00
          • Biking across the remote, beautiful, and untouched Jebel Sirwa mountains
          • Exploring crumbling remains of the past in Morocco’s many kasbahs
          • Riding a huge variety of rewarding tracks and trails
          • Sleeping under the stars in the Sahara Desert
          • Relaxing in one of Morocco’s most beautiful palm oases
          • Strolling through the spellbinding network of souks in Marrakech medina
          Photo Highlights Dates
          Self-Guided
          Self-Guided
          Italy

          Strade Bianche Explorer

          Self-Guided Gravel Bike Tour

          Duration

          8 days

          Prices from

          $2,480 P.P.
          1
          2
          3
          4
          5
          Grade 3-4 : Moderate/Chellenging
          More Info BOOK NOW

          Strade Bianche Explorer

          Self-Guided Gravel Bike Tour

          SAVE ON 2026 ESCAPES

          Save $125 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.

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

          2025 24 Mar – 29 Oct (excluding dates throughout July and August)

          Season 1 – $2480 24 Mar – 16 Jun and 03 Sep – 29 Oct

          Season 2 – $2780 17 Jun – 30 Jun and 01 – 02 Sep

          2026 29 Mar – 26 Oct (excluding dates throughout July and August)

          Season 1 – $2610 29 Mar – 14 Jun and 09 Sep – 26 Oct

          Season 2 – $2925 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.

          SAVE ON 2026 ESCAPES

          Save $125 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.

          • 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 Tour

          Duration

          8 days

          Prices from

          $3,135 P.P.
          View Reviews
          4
          1
          2
          3
          4
          5
          Grade 3-4 : Moderate/Chellenging
          More Info BOOK NOW

          Tuscany - Strade Bianche Explorer

          Guided Gravel Riding Tour

          SAVE ON 2026 ESCAPES

          Save $125 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 DateEnd DatePrice p.p.
          * 09/05/202616/05/2026$3,135.00
          * 20/09/202627/09/2026$3,135.00
          • 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
          Self-Guided
          Self-Guided
          Italy

          Tuscany - Pisa to Florence

          Self-Guided Leisure Bike Tour

          Duration

          8 days

          Prices from

          $1,850 P.P.
          View Reviews
          5
          1
          2
          3
          4
          5
          Grade 2-3: Gentle/ Moderate
          More Info BOOK NOW

          Tuscany - Pisa to Florence

          Self-Guided Leisure Bike Tour

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

          2025 24 Mar – 29 Oct (excluding dates throughout July and August)

          Season 1 – $1850 24 Mar – 16 Jun and 03 Sep – 29 Oct

          Season 2 – $2125 17 – 30 Jun and 01 – 02 Sep

          2026 29 Mar – 26 Oct (excluding dates throughout July and August)

          Season 1 – $1950 29 Mar – 14 Jun and 09 Sep – 26 Oct

          Season 2 – $2235 15 – 30 Jun and 01 – 08 Sep

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

          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
          Cuba

          Cuban Revolutions

          Guided Bike Tour

          Duration

          15 days

          Prices from

          $4,920 P.P.
          View Reviews
          24
          1
          2
          3
          4
          5
          Grade 2 - 3: Moderate/ Active
          More Info BOOK NOW

          Cuban Revolutions

          Guided Bike Tour

          Start DateEnd DatePrice p.p.
          08/11/202522/11/2025$4,920.00
          22/11/202506/12/2025$4,920.00
          24/01/202607/02/2026$5,195.00
          07/02/202621/02/2026$5,195.00
          07/11/202621/11/2026$5,195.00
          21/11/202605/12/2026$5,195.00
          • Kicking back with a post-ride Mojito
          • Cycling around the loaf-shaped mountains of Viñales
          • Exploring the cultural delights of Trinidad and Santiago
          • Cuban salsa beats in downtown Havana
          • Stories of Che, Castro and the Revolution
          • Cycling the Caribbean coast of Marea del Portillo
          Photo Highlights Dates
          Self-Guided
          Self-Guided
          Italy

          Classic Tuscany

          Self-Guided Leisure Bike Tour

          Duration

          7 days

          Prices from

          $1,910 P.P.
          View Reviews
          7
          1
          2
          3
          4
          5
          Grade 3 : Moderate
          More Info BOOK NOW

          Classic Tuscany

          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. 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.

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

          2025 24 Mar – 29 Oct (excluding dates throughout July and August)

          Season 1 – $1910 24 Mar – 16 Jun and 03 Sep – 29 Oct

          Season 2 – $2250 17 Jun – 30 Jun and 01 – 02 Sep

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

          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.

          • Staying at Tuscan farms overlooking stunning countryside
          • Visiting the famous towns of Monteriggioni, Radda in Chianti and Siena
          • Riding through wonderful landscapes, wide open fields, cypress-lined hills and vineyards
          • Trying delicious, regional dishes
          • Sampling the best wines of Chianti, Montepulciano and Montalcino
          • Absorbing the atmosphere of San Gimignano – a UNESCO World Heritage Site
          Photo Highlights Dates
          Self-Guided
          Self-Guided
          Italy

          Tuscany - Giro della Toscana

          Self-Guided Road Bike Tour

          Duration

          8 days

          Prices from

          $2,325 P.P.
          View Reviews
          4
          1
          2
          3
          4
          5
          Grade 3: Moderate
          More Info BOOK NOW

          Tuscany - Giro della Toscana

          Self-Guided Road Bike Tour

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

          2025 24 Mar – 29 Oct (excluding dates throughout July and August)

          Season 1 – $2325 24 Mar – 16 Jun and 03 Sep – 29 Oct

          Season 2 – $2750 17 Jun – 30 Jun and 01 – 02 Sep

          2026 29 Mar – 26 Oct (excluding dates in July and August)

          Season 1 – $2425 29 Mar – 14 Jun and 09 Sep – 26 Oct

          Season 2 – $2895 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.

          • Cycling through the historic wine regions of Tuscany, stopping off for a bit of wine tasting along the way
          • Staying in quality accommodation, with fantastically warm hospitality
          • Easing along the rolling hills of the ‘Colli Sienesi’
          • Riding the stunning UNESCO heritage region of Val d’Orcia
          • Stopping off at the lovely San Gimignano and Montalcino
          • Chilling out with a post-ride Chianti
          Photo Highlights Dates
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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
          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
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          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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