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.
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Destinations (74)
Types of Cycling / Grades (7)
Departure Month
Level of Support
Destinations (74)
Types of Cycling / Grades (7)
Departure Month
Level of Support
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Guided
Cuban Revolutions
Guided Bike Tour
| Start Date | End Date | Price p.p. |
|---|---|---|
| 07/02/2026 | 21/02/2026 | $5,195.00 |
| 21/11/2026 | 05/12/2026 | $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
Self-Guided
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.
| Start Date | End Date | Price p.p. |
|---|---|---|
| 06/05/2026 | 13/05/2026 | $2,135.00 |
| 25/09/2026 | 02/10/2026 | $2,135.00 |
Daily departures available. The season prices below are per person and are applicable for all start dates between and inclusive of the stated dates.
2026 29 Mar – 26 Oct (excluding dates throughout July and August)
Season 1 – $2425 24 Mar – 16 Jun and 03 Sep – 29 Oct
Season 2 – $2850 15-30 Jun and 01-08 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, Buonconvento, Asciano 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
Self-Guided
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.
2026 29 Mar – 26 Oct (excluding dates in July and August)
Season 1 – $2565 29 Mar – 14 Jun and 09 Sep – 26 Oct
Season 2 – $2995 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
Guided
Tuscany - Giro della Toscana
Guided Road Bike Tour
| Start Date | End Date | Price p.p. |
|---|---|---|
| 02/05/2026 | 09/05/2026 | $2,995.00 |
| 31/05/2026 | 07/06/2026 | $2,995.00 |
| 29/08/2026 | 05/09/2026 | $2,995.00 |
| 03/10/2026 | 10/10/2026 | $2,995.00 |
- 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
Self-Guided
Granada to Seville
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. 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 Date | End Date | Price p.p. |
|---|---|---|
| 31/05/2026 | 08/06/2026 | $2,425.00 |
| 18/10/2026 | 26/10/2026 | $2,425.00 |
Daily departures available. The season prices below are per person and are applicable for all start dates between and inclusive of the stated dates.
2026 01 Mar – 30 Nov (excluding dates from 29 Mar – 05 Apr / 01 Jul to 05 Sep)
Season 1 – $2710 01 – 28 Mar / 06 Apr – 30 Jun / 06 Sep – 30 Nov
Alternatively for a great value holiday choose one of our scheduled departures below.
- Cycling between 3 of the most magnificent cities in Andalucia
- Travelling through rolling sierras and olive plantations
- 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
Self-Guided
Azure Ocean Ride
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. 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.
2026 05 Jan – 13 Dec (excl. Easter week between 29 Mar and 05 Apr and St John’s Day 23/24 Jun)
Season 1 – $2610 05 Jan – 30 Jun and 16 Sep – 13 Dec
Season 2 – $3135 01 Jul – 15 Sep
Worth noting We run this tour from Jan through to Dec. The summer months however (generally from 01 Jul – 15 Sep) can be really busy. More people, more cyclists, busier restaurants, busier hotels etc, so we’d recommend travelling in the Spring or Autumn if you‘re looking for a quieter getaway with less cyclists to share the route with.
Please note We are generally not able to confirm any bookings for this tour made within 4 weeks of departure. Please contact our office if you are looking to book and begin your holiday within this period and we will do our best to accommodate your request.
- Discovering Portugal’s most beautiful beaches
- Cycling alongside the Ria de Aviero, a 40km stretch of blue lagoon
- Helping the fishermen with their catch in Praia da Vieira
- Enjoying the views of the western shoreline from the Sitio viewpoint
- Exploring the historical, castle walled village of Óbidos
- Visiting the lovely Vimeiro
Self-Guided
Lake Garda to Venice
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.
Daily departures available. The season prices below are per person and are applicable for all start dates between and inclusive of the stated dates.
2026 18 Apr – 26 Oct (excluding dates throughout July and August)
Season 1 – $2665 18 Apr – 14 Jun and 09 Sep – 26 Oct
Season 2 – $2995 15 Jun – 30 Jun and 01 – 08 Sep
If you‘re looking for a longer holiday, our Via Claudia route links into this tour perfectly; two self-guided tours of a similar grade that you‘re able to do back to back. Contact us if you’d like more info on this!
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.
- Enjoying a swim in Lake Garda
- Cycling along Pellestrina Island surrounded by Venetian lagoons and fishing boats
- Absorbing the hidden Rennaisance gems of the ‘belpaese’
- Exploring Verona – a piece of art in itself
- Discovering the medieval fortification of Montagnana
- Taking a gondola ride along the canals of Venice
Self-Guided
Lake Garda to Venice
Self-Guided Family 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.
2026 18 Apr – 26 Oct (excluding dates throughout July and August)
Season 1 – $2665 18 Apr – 14 Jun and 09 Sep – 26 Oct
Season 2 – $2995 15 Jun – 30 Jun and 01 – 08 Sep
We can offer the following discounts for children under 18:
We can offer a 20% discount for any child under 18 travelling with 2 fully-paying passengers. If you’re happy to share a family room (where available) we can often offer an additional 10% – please chat to our team about your preferred rooming arrangements.
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.
- Enjoying a swim in Lake Garda
- Cycling along Pellestrina Island surrounded by Venetian lagoons and fishing boats
- Absorbing the hidden Rennaisance gems of the ‘belpaese’
- Exploring Verona – a piece of art in itself
- Discovering the medieval fortification of Montagnana
- Taking a gondola ride along the canals of Venice
Self-Guided
Tuscany - Sacred Routes
Self-Guided Mountain 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.
2026 29 Mar – 26 Oct (excluding dates throughout July and August)
Season 1 – $2565 29 Mar – 14 Jun and 09 Sep – 26 Oct
Season 2 – $2850 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.
- Staying in lovely Tuscan accommodation overlooking stunning landscapes
- Riding the Montagnola trails, the location of a well-known Sienese MTB race
- Sampling the best wines of Chianti, Montepulciano and Montalcino
- Riding down the “Crete Senesi” on a roller coaster ridge ride
- Enjoying the journey across Tuscany on a variety of terrain
- Visiting the famous hilltop towns of San Gimignano, Monteriggioni, San Quirico d‘Orcia and Pienza
Guided
Tuscany to Rome
Guided Electric Bike Tour
E-BIKE TOUR
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 Date | End Date | Price p.p. |
|---|---|---|
| 23/05/2026 Guaranteed | 30/05/2026 | $3,425.00 |
| 12/09/2026 | 19/09/2026 | $3,425.00 |
- 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
Not sure which trip's right for you? Just ask!
Get in touch and we'll help you find your perfect trip.
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