Top 10 challenging cycling holidays
Glamour, Lycra, speed, power: cycling is a potent way to take on a destination. The most energy efficient form of transport there is, travelling frictionlessly by bike can make you so at one with your machine, it’s not clear where it ends and you begin. These are holidays where you can say, “I did it,” or point to a mountainous skyline and say, “I was up there.”
What makes our cycling challenges different? Many of them directly benefit communities and nature, whether you’re raising sponsorship money for your own Tour de France, or visiting NGOs along the way. E-bikes are available on a lot of rides – so you can tackle challenging landscapes with a bit more support.
Ready to roll? Browse our top 10 challenging cycling holidays.
What makes our cycling challenges different? Many of them directly benefit communities and nature, whether you’re raising sponsorship money for your own Tour de France, or visiting NGOs along the way. E-bikes are available on a lot of rides – so you can tackle challenging landscapes with a bit more support.
Ready to roll? Browse our top 10 challenging cycling holidays.
1. Cycle stages of the Tour de France for charity
This is the big one. Cycle parts of the famous Tour de France for charity, a week ahead of the actual race. On this fully supported ride you can cycle nine stages of the Tour de France and raise money for a charity that helps disadvantaged children as you go. This route takes sections of tours past – a bit of 2005 in reverse, a sprinkling of the Tour de Femmes 2026 – and stitches them together to make an epic ride in the south of France. Yes, Mont Ventoux features, of course. No survey of the Tour de France would be complete without this famously epic climb, and the victorious descent afterwards.
Best time to go: June
Our top selling trip: Tour de France cycling holiday
Best time to go: June
Our top selling trip: Tour de France cycling holiday
2. Tour Aotearoa: cycle the length of New Zealand
“Aotearoa is a ridiculously diverse country,” says Alice Baker, from our partner for New Zealand cycling holidays. She has cycled the length of both islands on the Tour Aotearoa. “When we drove up to Northland to start the tour, it felt like we had landed on a sleepy tropical island with vast beaches, rolling sand dunes and laid-back village vibes. Then you start riding and just as quickly you’re in Auckland city, then the volcanic valleys of the Central North Island.” Most people who come to New Zealand want to see both islands – but very few of them could say that they’ve seen both islands end-to-end by bike. Cycle rides like this are difficult to organise for yourself so get an expert support team with a sag wag on your side. Challenge: accepted.Best time to go: February
Our top selling trip: Cycle the whole of New Zealand
3. Big backroad climbs cycling in Sri Lanka
A highlight of cycling in Sri Lanka? The 85km ride between Kandy and Nuwara Eliya through Sri Lanka’s hill country, a challenging climb into tea-cultivation country. But if you don’t fancy the journey, the backup option is a tourist attraction in and of itself: a very scenic train ride to Nanu Oya. Once you’ve explored hill country, enjoy a glorious descent through Uva Province. Sri Lanka is hot, tropical and hilly for cycling, but it’s also small, and you can cover lots of the country in two weeks, cycling all the way from Sigiriya to the coast, stopping at the temples, national parks and beaches along the way.Best time to go: All year round
Our top trip: Sri Lanka cycling holiday, off the beaten track
4. Freewheeling down the Western Cape: South Africa
It’s the scenery that will keep you going on the undulating roads around the dramatic mountains, cliffs and plateaus of South Africa’s Western Cape – such as the Hellshoogte Pass, which connects Franschhoek and Stellenbosch. As you cycle smooth turns, reaching deliciously high speeds, you’ll be whipping past some of the country’s most expensive wine estates, situated in seriously scenic valleys. Why go cycling here? Atlantic views, famous high passes, vineyard rides – and the possibility of lots of delicious lunches and dinners among the vines.
When to go: November to February
Our top trip: South Africa tailor made cycling adventure
When to go: November to February
Our top trip: South Africa tailor made cycling adventure
5. Land’s End to John o’ Groats
To the uninitiated, LEJOG sounds like a relaxing French jaunt around the park, but it’s the UK’s most challenging and prestigious long distance cycling route – taking you 1,500km from Land’s End, mainland UK’s most westerly point, to the village John o' Groats, close to its northernmost point. Things start with a bang in hilly Cornwall, and only progress from there. Climb in the Cornish hills, keep climbing in Dartmoor, head into Wales then dip back into England for the Lake District. Enter Scotland via Gretna Green and cycle along Loch Lomond, to Fort William, and via the Pass of Glencoe. Tackle the route over 14 days (the record is nine).Best time to go: September
Our top trip: Land’s End to John o’ Groats cycling trip
6. Pedal through Kerala & Tamil Nadu, South India
To cross from the state of Kerala to Tamil Nadu there’s just the small matter of the Western Ghats, a mountain chain that runs parallel to India’s west coast for 1,600km. Climbing by bike might be a challenge, but being up here in the highlands brings cooler temperatures, tea plantations, and forests filled with wild elephants. It’s a high point and a highlight on the route through South India, which sees you crossing coast to coast, starting in Kochi and ending with the historic seaside town of Mahabalipuram on the Bay of Bengal.Best time to go: January
Our top trip: South India cycling tour, coast to coast
7. Cycle the North Coast 500, Scotland
Voted one of the world’s top scenic coastal routes, the North Coast 500 has become an extremely popular driving route. Tackling it by bike is more challenging, but you’ll be even more appreciative the views on your feed stops. This 805km (500 mile – hence the name) goes via epic scenery: big rolling fells, lochs, coast. Highlights include climbing up the Bealach na Ba road and then the descent down the other side to the town of Applecross. Passing the UK mainland’s northernmost village, John o’ Groats, you might bump into cyclists celebrating the end of their LEJOG tour (see number 5 above) – maybe you can do that next.
Best time to go: August to September
Our top trips: North Coast 500 cycling tour in Scotland
Best time to go: August to September
Our top trips: North Coast 500 cycling tour in Scotland
8. Cycle across Montenegro
Durmitor National Park might be the most beautiful place for cycling in all of Montenegro – but it’s a close-run competition. Cycling across the country, which is only half the size of Wales, you could also drop in on Lovcen National Park and Lake Skadar National Park. Take a route that runs from the mountains all the way down to the Bay of Kotor on the sea. E bikes make it easier, but you can also use road or touring bikes. Just expect some steep sections, sometimes gaining elevations between 800 and 1,000m in a day, to earn those views.Best time to go: April to October
Our top trip: Trans-Montenegro cycling tour
9. Laos to Vietnam by bike
It’s hot, it’s sticky, it’s humid… but, boy, is it beautiful, and rewarding, too. Travel between Vientiane and Hanoi by bike, overnight train and support van. Along the way, activities might include camping, homestays, opportunities for hot air ballooning, sunrise treks and longtail boat cruising. There are also plenty of opportunities to visit community projects and contribute to the work of NGO-supported social enterprises, such as restaurants that provide training for disadvantaged local people. You get to try great food that does good – fuel for you and fuel for change.Best time to go: October to February
Our top trip: Cycle Laos to Vietnam, Vientiane to Hanoi
10. High altitude rides in South America
Prepare to vanish into thin air, cycling the crazy landscapes between San Pedro de Atacama in Chile and Salta in Argentina. You’ll feel like you’ve pedalled to another planet at the Valley of the Moon, watch sunrise over one of the world’s largest geyser fields, hear the crunch under your wheels on weird, sparkling salt pans and even end the ride in Germany… sort of… at a ghost town named Almania, after its German workers. It’s remote cycling in dry heat and difficult conditions. The high altitude (up to over 4,300m) isn’t the only thing that will take your breath away up here. As one reviewer put it ‘once-in-a-lifetime scenery, but every single day!’
Best time to go: April, May, September or October
Our top trip: Chile and Argentina cycling holiday
Best time to go: April, May, September or October
Our top trip: Chile and Argentina cycling holiday
More Cycling articles
Expand your pedalling parameters as you peruse our travel guide and discover new routes.
When working out where to go on a cycling holiday, remember to look off the beaten track.
Find out how you can explore the Middle East, Eastern Europe, Caribbean and Asia by bike.
These trips are for mountain bikers who feel comfortable on a red grade singletrack at a mountain biking centre.
Find out why your next holiday should be a cycling holiday. Let our travel experts state the case of the humble bicycle.
From fitness issues to wardrobe worries, our cycling holidays FAQs page has answers from the experts.
Read pro cycling tips from our experts, from what to pack to how much (or if) to train.
Find all of our cycling guides in one place, from particular countries to different types of cycling holidays.
