The Best October Cycling Holidays

Based on the experience of our team and customers, I’ve selected six of my favourite tours that are perfect for a late-season escape. If you have any questions or want to find out more about these stunning destinations, call our knowledgeable team on +44(0)1273 224066 or enquire online.

Let’s start off strong with our most popular tour for October 2025. Explore Portugal’s pristine west coast at a time of the year when the temperature is most suitable for cycling. Warm enough to escape the weather back home but avoiding the peak summer heat. You’ll still get to enjoy stunning sunsets on the beach and dips in the sea as well, as water temperatures are only 1°C less than in August! It's also quieter in October, allowing you to delve into Portuguese culture in two of Europe’s city gems.

Cycling through the rolling hills, you’ll pass some unmissable scenery. On Day 3, the Aveiro Lagoon and the protected São Jacinto dunes nature reserve await. There is also a ferry to Aveiro to visit the ‘Portuguese Venice’ with beautiful canals and decorative alleys. The highlights don’t stop there, from sand dunes to saltpans it really is one for coast lovers. Finishing the tour in Lisbon, one of the most appealing capitals in Europe, is the perfect end to a tour that promises to impress.

As the temperatures are cooler, why not try the extended 11-night version of this tour where you cycle the whole route without a transfer?

Our Sales Consultant, Evan, has cycled this tour himself - read his Fascinating Week on Two Wheels from Porto to Lisbon Trip Report.

"The holiday was very well organised with good hotels and well managed baggage transfer. The riding was mostly gentle and the transfer in the middle worked out fine. We managed to find good places to eat out and enjoyed the local beer and excellent coffee though being coastal based menus tended towards fish which might not suit all but sufficient alternatives were always available. The route maps and notes were really good. Very much a trip we enjoyed and can recommend to others, even if in your 70's and 80's like us!" - Jonathan Hawkins, UK

View tour: Porto to Lisbon Bike Tour

This scenic cycling tour through the green heart of Umbria offers the ultimate October Italian escape. Pedal past dramatic hills, peaceful valleys and shimmering lakes as you explore rustic hilltop villages and charming historic towns. October brings cooler temperatures and fewer crowds - ideal for steeper climbs on this moderate to challenging tour. When you arrive in Assisi’s hilltop beauty, enjoy discovering local markets or sipping wine on sun-drenched terraces.

Ride through breathtaking landscapes with hilly climbs and rewarding descents. Pause in Spello’s stone-paved streets or enjoy a rest day in the quiet village of Torgiano. From mountain monasteries to artisan workshops, every stop offers something unique. With daily departures throughout October, it’s flexible too.

Like the sound of Umbria but looking for a short break? Take a look at our Umbrian Escape Bike Tour. Or wanting to go for longer? Try our Umbria Discovery Extended Bike Tour.

"Beautiful and historic area with well organised routes, very good accommodation and wonderful Umbrian food. Top Tip: Don't be put off by the challenging route as a couple of our group switched to e-bikes after 2 days and were able to relax more to complete routes in what was exceptional heat." - David Heslop, UK

View tour: Umbria Discovery Bike Tour

Cycling through rural mountain villages and historic cities, this route is a hidden gem. Glide past architectural history such as 13th-century churches, fortresses and the castle at Alcalá la Real. Some sections provide the chance to push yourself, but there is an option to take a transfer on the most demanding cycling day.

It’s also a culinary dream come true for foodies - don’t miss the chance to try the mouthwatering local dishes. The specialities range from cheeses and tapas to stuffed peppers and Spanish omelette. And you can finish off the tour with a visit to a local bodega (wine cellar) to sample the local wines! Visiting in October offers a unique opportunity to blend in with the locals and visit popular sights like the Alhambra Palace without the crowds.

"Fantastic tour around beautiful hilltop towns in Andalusia. We loved the scenery - miles and miles of olive groves, cycling on quiet, stony farm tracks so didn’t have to worry about traffic. It was exciting to see a different and traditional side to this touristy region. All of the accommodation was great. Bikes were sturdy, good quality and well maintained. Two of the rides were fairly challenging with lots of hills and the autumn weather was perfect temperature to ride. The local tour operator was excellent and messaged us most days; her welcome meeting was really informative." - Sarah-Jane Morrow, UK

View tour: Granada to Cordoba Bike Tour

Gorgeous lakes, steaming thermal pools and a glorious national park. Experienced cyclists will find themselves in cycling heaven in this guided tour of Albania. Pedalling towards the Benja Thermal Baths and seeing the steam rise on day five is a truly unforgettable experience. This challenging tour puts you to the test, but be safe in the knowledge that a support van is on hand if necessary. The English-speaking guides are personable and experienced, ensuring you see all the highlights along the way. I recommend an October trip due to the more favourable prices, while the temperature is ideal for cycling.

In Albania, the natural beauty is endless. The views make this one of the most rewarding trips we offer. Combined with the visits to Lake Ohrid, Langarica Canyon and the Albanian Riviera, I couldn’t recommend this tour more to confident cyclists. And I haven't even mentioned the ancient ruins of Butrint, or the beach you’ll swim from at Himarë yet! Two departure dates have already sold out and two are left available in October 2026, I recommend you book this one fast!

Our Assistant Operations Manager, Darryl, has cycled this tour himself - read about his Highlights of Albania Trip Report.

“This was my first cycling tour and it did not disappoint! The right level - exactly what I was looking for. Dhimitri, the local guide was personable and very knowledgeable. Bato, the driver was helpful and encouraging when I was always at the back of the queue! We all bonded as a team and laughed all the way. The food was amazing. Albania is a hidden gem. The booking team at Freedom Treks was also excellent. Although I rarely go back to the same country twice, I plan on doing another tour there soon.” - Zahidah, UK

View tour: Highlights of Albania Guided Bike Tour

From diverse wildlife aplenty to stunning monuments left by the Spanish Conquistadors, this unique tour is one for the explorers. Visiting in October allows you to experience the heart of mainland Spain in favourable temperatures. But don’t worry, you’ll still see plenty of wildlife as you ride past lustrous pastures and reach Monfrague National Park - birds of prey, Spanish Ibex, wild bulls and Iberico pigs to name a few.

Along the way, you'll rest your feet at carefully selected accommodations - including stays in paradors on certain nights. These are luxury hotels located in restored palaces, castles and monasteries and will add to the sense of adventure. Stunning cities are another highlight of the tour, home to monuments left behind by the Conquistadors. Delve into their history and the impact they had on the area. This tour is labelled as ‘moderate’ difficulty, so it’s best for more experienced cyclists, but e-bikes are also available for extra pedal power.

“An excellent way to get a sense of Extremadura; magnificent scenery; the history; the culture. The accommodation was an experience in itself. Each Parador had a magnificence of its own, and the Finca Palacio Viejo de Las Curchuelas provided us with a dark sky light show (after a home-produced dinner on the terrace, overlooking the dehesa) to a soundtrack of gently chiming sheep bells, the chirping and buzzing of crickets and katydids, and the bellowing and grunts of stags. Most of the cycling is on tarmac roads, but there was little traffic during most of the cycling, except for the final couple of kilometres into Cáceres.” - Iain Noble, UK

View tour: Spain's Conquistadors & Paradors Bike Tour

I’m sure you’ve heard that Sicily is stunning, but that really is an understatement. In a region of astounding natural beauty, you’ll cycle through four UNESCO-listed World Heritage Baroque towns. The mind-boggling landscapes are the perfect backdrop for a relaxing ride. October is one of the quieter months, making it perfect for cycling in peaceful bliss on the leisurely tracks. The warmth that comes from the Mediterranean is still apparent but it remains cool enough for pleasant cycling.

The blend of nature and cities is a real plus for this tour. Sicily’s crystal clear rivers and lagoons at Vendicari Nature Reserve are of real contrast to the ancient sites in the city of Ragusa and the Baroque cathedral in Modica. Not to mention the spectacular palaces and glistening domes in Noto. End your days with exquisite local cuisine such as seafood pasta and local wines. I highly recommend Sicily to any cyclist comfortable with its moderate difficulty. There are daily departures throughout October which provides maximum flexibility.

“My wife and I recently enjoyed the Sicily - Baroque Routes bike tour. To review it in a single word, we would simply say fantastic! First, the organization was perfect, from pick-up in Nicolosi to the end of the tour. Second, the weather was really kind to us: sunny days from first to last day! The bikes provided were in very good condition. Third, the routes were nice, well designed and easy to follow with the GPS device mounted on the bike. Lastly, the hotels we stayed were great options: Sacre Pietre in Anapo Valley: great food; Il Barroco in Ragusa Ibla: very nice hotel, with the best shower I've had; La Corte Del Sole in Noto: nice hotel, nice restaurant, and best of all: walking distance to a very nice beach, where we went to refresh after our bike rides.” - Claudio Lordello

View tour: Sicily's Baroque Routes Bike Tour

The wonderful island of Madeira has a mild year-round climate, making it an essential October destination for sun-seeking cycling enthusiasts. This trip runs year-round, but I recommend October for the kinder prices and the cooler-than-usual weather. Following the island’s rolling coastline, this is a testing tour tailored to more experienced cyclists. Embrace the challenge of climbing the ascent to Europe’s highest cape, where a glass platform suspends 580m above the sea. But have the peace of mind that the steepest and longest climbs have transfers.

This tour allows you to explore all areas of the sub-tropical island. You will get many spectacular sea views which are stunning on both the ascents and descents. There are also multiple opportunities to take a break from pedalling. With a volcanic sand beach and 400,000-year-old grottoes, this tour has a range of unique stops. After the culmination of your cycling, reward yourself on the final day by going bike-free. Dive into Madeiran culture in the capital city of Funchal and experience its grand quintas, tropical garden, wicker sledge ride and levada paths.

"Loved this tour, really enjoyable. The routes were well thought out and the locations and hotels booked were all good with a couple that were exceptional. A couple of days were pretty tough, Madeira is very hilly, and I probably wouldn't recommend it to non cyclists unless with an e bike. Great trip, thank you. Loved it." - Sarah Roberts, UK

View tour: Madeira Bike Tour

All the tours above still have availability for October 2026. View October dates and prices and book online through the tour pages, or call our friendly team on +44 (0)1273 224066 for more advice.

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