The Best September and October Cycling Holidays

September and October are possibly our favourite months of the year for a cycling holiday. Routes are beginning to get less busy after the summer rush, temperatures are more comfortable and attractions are quieter than in the middle of summer. You may also be able to find notably cheaper flight prices for departures at this time of year.

With this in mind we asked Catherine, Head of Freedom Treks, to select her favourite tours for cycling in autumn. Read on below to discover her selection of five holidays that are perfect for a late escape.


Lecce Duomo, Puglia
Piazza del Duomo in Lecce
  • Self-guided tour
  • Average September temperature: 21°C / 70°F | Average October temperature: 17°C / 63°F
  • Friday & Saturday departures

Catherine says: Italian sun-worshippers flock to the heel of Italy in August for their summer holidays, but come September & October it is significantly quieter. The weather is still warm, but temperatures cool down so conditions are perfect for cycling through the region's olive groves, hilltop towns and pretty seaside villages. I went myself in October and it was still lovely and warm. The coastline of Puglia is the longest and one of the most gorgeous and diverse in Italy - sea temperatures averaging around 25 degrees mean you can enjoy swimming in the Ionian and Adriatic seas.

View tour: Puglia


Bolzano Castle, Italy
Tirol Castle in Bolzano

Tirol Castle in Bolzano

  • Self-guided tour
  • Average September temperature: 19°C / 66°F | Average October temperature: 16°C / 61°F
  • Daily departures

Catherine says: The South Tyrol region of northern Italy, for which Bolzano is the capital, enjoys a mild climate and comfortable cycling conditions all the way until mid-October. Autumn time in South Tyrol is harvest time; orchards and vineyards are full to the brim with ripened crops ready to be reaped, and the ancient tradition of the “Törggelen” wine tasting comes to life. The colours of the hillsides as you cycle along the Adige cycle path and beyond are really memorable and local towns (including Trento and Brixen) have fewer tourists, meaning more space to explore the many historic cathedrals, colourful shops and cosy restaurants.

View tour: Bolzano from One Hotel


Baroque architecture, Ibla, Sicily
The beautiful town of Ibla, Sicily

The beautiful town of Ibla, Sicily

  • Self-guided tour
  • Average September temperature: 21°C / 70°F | Average October temperature: 17°C / 63°F
  • Daily departures

Catherine says: The warm wind that blows across the Mediterranean from Africa keeps the southern Italian island of Sicily warm in September and October but cool enough for exploring beautiful UNESCO-listed Baroque towns. Dazzling landscapes are the ideal backdrop for relaxing rides, stopping in beautiful towns including Noto, with its sparkling domes and resplendent palaces and Modica, which is home to a spectacular Baroque cathedral. Reward yourself at the end of the day with a plate of seafood pasta and a glass of exquisite Sicilian wine.

View tour: Sicily - Baroque Routes

Istrian Coast

Rovinj harbour in Croatia
Rovinj harbourfront in Croatia

Rovinj harbourfront in Croatia

  • Guided tour
  • Average September temperature: 19°C / 66°F | Average October temperature: 16°C / 60°F
  • Sunday departures

Catherine says: This boat & bike tour of Croatia’s spectacular Istrian coast is an adventure with a wonderful mix of cycling, sailing and exploring. Journey down the coast, stopping in historic harbour towns for rides inland on gentle trails. You will stay aboard a beautiful two-mast yacht with a sun deck, perfect for lapping up the late summer sun and even taking a dip in the Adriatic, which still averages sea temperatures of around 20°C / 68°F at this time of year!

Departures for this tour are still available for 1, 8th and 15th October 2017.

View tour: Istrian Coast


Funchal square in Madeira
Funchal, Madeira

Funchal, Madeira

  • Self-guided tour
  • Average September temperature: 23°C / 73°F | Average October temperature: 21°C / 70°F
  • Tuesday, Thursday & Saturday departures

Catherine says: The beautiful Portuguese island of Madeira sits off the coast of Africa, above the Canary Islands. Famed for walking holidays, it also makes a fantastic destination for a cycling tour. This island has a mild, year-round climate, meaning that even if you can’t make September or October, you can escape grey winter skies and cycle in the gorgeous sub-tropical sunshine! The quiet coastal cycling routes take you by exotic flowers and gardens which decorate the island, through villages to see ancient grottoes and traditional thatched houses. The steepest and lengthiest climbs are softened with transfers.

View tour: Madeira

Find out more

If you would like to know more about this holiday, make an enquiry online or speak to one of our team by telephone: +44 (0)1273 224066 (Office Hours (UK time): Monday to Friday: 9am - 5.30pm)

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Tours featured in this post