Most cycling holidays are sold with photos of lean people in Lycra effortlessly cresting an Alpine pass. Most of us are not those people. We want to see somewhere beautiful at the pace of a bike, stop for coffee whenever we like, and know that when our legs file a formal complaint, a support van will appear with water, snacks and a seat. Good news: that’s exactly how most guided cycling holidays work.
This guide ranks our cycling holidays by how much they’ll hurt, from flat river paths you could ride after a big lunch to proper climbs over the Andes. The “pain score” is our own rough guide, based on each trip’s physical rating and route; every tour page has the details.
The quick answer
- Barely hurts: the Otago Central Rail Trail, the Danube from Vienna to Budapest and the mostly downhill Dolomites to Venice.
- A good workout: Spain’s Mediterranean coast, northern Vietnam and western Cuba.
- You’ll feel it: the Croatian islands, the Cape and Albania.
- Bring your legs: Sri Lanka’s tea country and the Andes.
Cycling holidays compared, gentlest first
| Tour | Days | Price from | Physical rating | Group size | Flights included | Best for |
|---|---|---|---|---|---|---|
| Pain score 1: barely hurts | ||||||
| Cycle New Zealand: The Otago Central Rail Trail – 4 Days | 4 | £846 pp | Low | Max 12 | No | A rail trail, gentle gradients |
| Cycle the Danube: Vienna to Budapest – 8 Days | 8 | £1,840 pp | Medium | Max 15 | No | Flat river paths |
| Cycling from the Dolomites to Venice – 8 Days | 8 | £1,209 pp | Medium | Not stated | No | Mostly downhill or flat (self-guided) |
| Pain score 2: a good workout | ||||||
| Cycle Prague to Vienna: Bohemia & the Danube – 8 Days | 8 | £2,095 pp | Medium | Max 15 | No | Flat Danube, some Bohemian hills |
| Cycling Spain’s Mediterranean Coast: Barcelona to Valencia – 8 Days | 8 | £2,963 pp | Medium | Max 16 | No | Coast and railway paths |
| Cycling in Western Cuba: Havana, Viñales & Cayo Jutías – 7 Days | 7 | £875 pp | Medium | Max 16 | No | A few short climbs |
| Cycling Southern Thailand: Bangkok to Ao Nang – 9 Days | 9 | £1,076 pp | Medium | Max 16 | No | Jungle to beach |
| Cycle Northern Vietnam: Mai Chau, Pu Luong & Ha Long Bay – 8 Days | 8 | £896 pp | Medium | Max 16 | No | Valleys and some hills |
| Pain score 3: you'll feel it | ||||||
| Cycle Croatia: Split, Hvar, Korčula & Dubrovnik – 7 Days | 7 | £2,095 pp | Medium | Max 16 | No | Hilly islands in the heat |
| Cycling Jordan: Petra & Wadi Rum by Bike – 9 Days | 9 | £1,715 pp | Medium | Max 16 | No | Hills and desert |
| Cycling the Cape & Winelands – 12 Days | 12 | £2,911 pp | Medium | Max 14 | No | Mountain passes and coast |
| Cycling in Albania: Mountains to the Riviera – 8 Days | 8 | £1,695 pp | Medium | Max 16 | No | Some long climbs |
| Cycling in Georgia: Cave Towns & Wine Country – 9 Days | 9 | £1,645 pp | Medium | Max 16 | No | Hills to Vardzia |
| Pain score 4: bring your legs | ||||||
| Cycling in Japan: Kanazawa Coast to Kyoto – 14 Days | 14 | £6,306 pp | Medium | Max 14 | No | One challenging mountain day |
| Cycle the Back Roads of Sri Lanka – 14 Days | 14 | £2,447 pp | Medium | Max 16 | No | A long tea-country climb |
| Cycling the Lake District of Chile & Argentina – 13 Days | 13 | £4,919 pp | Medium | Max 16 | No | Andes crossings |
Prices are per person, twin share, live from our tour pages (updated October 2026). The lowest price can apply to a later departure, so check the dates you want on each tour page.
Ask us which ride fits your legs →
How guided cycling holidays work
A leader and a support vehicle. On the guided trips, a leader rides with you and a support vehicle carries your luggage, water and anyone who’s had enough. Hopping in the van isn’t cheating; it’s strategy.
Bikes provided. Hybrid, touring or mountain bikes are included; each tour page says which.
Not a race. Groups ride at their own pace, regrouping at stops.
Pain score 1: barely hurts
Cycle the Otago Central Rail Trail
Cycle New Zealand: The Otago Central Rail Trail – 4 Days
- 4 days
- From £846 per person
- Max 12 people
- Starts and ends in Queenstown, New Zealand
- Physical rating: low
- Flights not included
- Departures in January, February, March, April, September, October, November, December
Four days along an old gold-fields railway in New Zealand’s Central Otago, with gentle gradients, rides of up to 55km, a leader cycling with you, bike hire and luggage moved between a guesthouse, cottage and hotel.
The honest drawback: it’s short, and a long way to go for four days, so pair it with a wider New Zealand trip.
Cycle the Danube: Vienna to Budapest
Cycle the Danube: Vienna to Budapest – 8 Days
- 8 days
- From £1,840 per person
- Max 15 people
- Vienna, Austria to Budapest, Hungary
- Physical rating: medium
- Flights not included
- Departures in April, May, June, July, August, September, October
Eight days on mostly flat, dedicated cycle paths with a leader and support vehicle: Vienna’s palaces and parks, the riverside forests of the Donau-Auen National Park, Bratislava, Győr, Komárom, Esztergom’s basilica and the Danube Bend to Budapest.
The honest drawback: you ride most days, and it’s just one night in Budapest.
Cycling from the Dolomites to Venice (self-guided)
Cycling from the Dolomites to Venice – 8 Days
- 8 days
- From £1,209 per person
- Dobbiaco, Italy to Mestre, Venice, Italy
- Physical rating: medium
- Flights not included
- Departures in May, June, July, August, September
Eight days following old railway lines and rivers from the high Dolomites down to the Venetian lagoon, with a quality bike, route notes and luggage moved: Cortina d’Ampezzo, Belluno, Feltre, the Brenta Valley to Bassano del Grappa, Treviso and the River Sile to Venice. There’s no group or leader.
The honest drawback: it’s self-guided, so you’ll need to navigate yourself, and it’s not for complete beginners.
Pain score 2: a good workout
Cycling Spain's Mediterranean Coast
Cycling Spain’s Mediterranean Coast: Barcelona to Valencia – 8 Days
- 8 days
- From £2,963 per person
- Max 16 people
- Barcelona, Spain to Valencia, Spain
- Physical rating: medium
- Flights not included
- Departures in April, May, August, September, October
Eight days from Barcelona to Valencia on quiet roads and car-free paths with a leader and support vehicle: Sitges to Altafulla, a disused railway line to medieval Tortosa, the wildlife-rich Ebro Delta, the Sierra de Irta Natural Park and a final ride round Valencia. Hotels have pools and sea views.
The honest drawback: only breakfasts and a welcome dinner are included.
Cycle Northern Vietnam
Cycle Northern Vietnam: Mai Chau, Pu Luong & Ha Long Bay – 8 Days
- 8 days
- From £896 per person
- Max 16 people
- Starts and ends in Hanoi, Vietnam
- Physical rating: medium
- Flights not included
- Year-round departures
Eight days with a leader and support vehicle: a ride through Hanoi’s traffic (exhilarating is one word for it), the valley of Mai Chau and the rice terraces of Pu Luong with two nights in stilt-house homestays, Cuc Phuong National Park, Ninh Binh and a night on a boat in Ha Long Bay.
The honest drawback: some hills, and the homestays have shared rooms.
Also in this group: Cycle Prague to Vienna (8 days, rides of up to 70km, mostly flat with some Bohemian hills), Cycling in Western Cuba (7 days, a few short climbs) and Cycling Southern Thailand (9 days, from jungle to the beach at Ao Nang, with the heat as the main challenge).
Pain score 3: you’ll feel it
Cycling the Cape & Winelands
Cycling the Cape & Winelands – 12 Days
- 12 days
- From £2,911 per person
- Max 14 people
- Starts and ends in Cape Town, South Africa
- Physical rating: medium
- Flights not included
- Departures in March, September, October, November, December
Twelve days with a leader and support vehicle: over Hellshoogte to Stellenbosch, up the Franschhoek Pass, into the Karoo and the Langeberg Mountains, Cape Agulhas at the tip of Africa, a free day for whale watching in Hermanus, the Whale Coast, the Cape Peninsula with its penguins and Chapman’s Peak.
The honest drawback: mountain passes, and only breakfasts and a welcome dinner are included.
Cycling Jordan: Petra & Wadi Rum
Cycling Jordan: Petra & Wadi Rum by Bike – 9 Days
- 9 days
- From £1,715 per person
- Max 16 people
- Starts and ends in Amman, Jordan
- Physical rating: medium
- Flights not included
- Departures in March, April, May, September, October, November
Nine days from the northern hills to the Red Sea: Jerash, olive groves to Madaba, Mount Nebo and the Dead Sea, Petra on foot and by bike to Little Petra, the Wadi Araba down to Aqaba, and a night at a Bedouin camp in Wadi Rum with a jeep safari.
The honest drawback: heat and hills, and few meals are included.
Also in this group: Cycle Croatia (7 days, island-hopping with hills and heat), Cycling in Albania (8 days, some long climbs from the mountains to the Riviera) and Cycling in Georgia (9 days, cave towns, the climb to Vardzia and wine country).
Pain score 4: bring your legs
Cycle the Back Roads of Sri Lanka
Cycle the Back Roads of Sri Lanka – 14 Days
- 14 days
- From £2,447 per person
- Max 16 people
- Sigiriya, Sri Lanka to Colombo, Sri Lanka
- Physical rating: medium
- Flights not included
- Departures in January, February, March, April, July, September, October, November, December
Fourteen days with a leader and support vehicle on quiet back roads: Sigiriya at dawn, Dambulla, Polonnaruwa by bike, spice country to Kandy, then the big one, a long climb through tea estates to Nuwara Eliya, before a hill-country ride to Ella and a long descent past the rock-cut Buddhas of Buduruvagala, a Yala safari and a beach day.
The honest drawback: that climb, in the heat. You’ll earn the descent.
Cycling the Lake District of Chile & Argentina
Cycling the Lake District of Chile & Argentina – 13 Days
- 13 days
- From £4,919 per person
- Max 16 people
- Puerto Varas, Chile to Temuco, Chile
- Physical rating: medium
- Flights not included
- Departures in February, March, October, November, December
Thirteen days crossing the Andes twice with a local cycling leader and support vehicle: Puerto Varas and Frutillar, beneath the volcanoes of Osorno and Calbuco to Petrohué, lake ferries including Todos los Santos and Nahuel Huapi, a rest day in Bariloche, araucaria forests and Villa Pehuenia. Nine lunches are included.
The honest drawback: paved and gravel roads with some challenging climbs, so regular cycling beforehand is a must.
Cycling in Japan (14 days) rides from the Sea of Japan coast through the Japanese Alps to Kyoto, with a night in a thatched farmhouse in Shirakawa-go and one challenging mountain day.
How to choose
Be honest about your fitness. If you ride occasionally, start with a pain score 1 or 2 trip. If you ride regularly, 3 is fun. Score 4 trips are for people who already know what a gradient feels like.
Mind the heat. Thailand, Sri Lanka, Jordan and Cuba add heat to the challenge, so choose cooler months.
By budget. Vietnam, western Cuba and Thailand are the best value; the Andes and Japan cost the most. Live prices are in the table above.
Frequently asked questions
What is the easiest cycling holiday?
The Otago Central Rail Trail and the Danube from Vienna to Budapest, on gentle rail trails and flat river paths.
Do I need to be fit for a cycling holiday?
You need to be comfortable riding several hours a day. On guided trips, a support vehicle can carry you if you need a break.
Are bikes provided?
Yes, bike hire is included on all of these trips. Each tour page says what type of bike you ride.
What is the hardest cycling holiday?
Cycling the Lake District of Chile & Argentina and Sri Lanka’s back roads, with long climbs.
Are there self-guided cycling trips?
Yes, Dolomites to Venice is self-guided, with route notes and luggage transfers.
Are flights included?
No, these trips are land-only, and we can arrange flights.
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Prices are live from our tour pages (updated October 2026). Tour details and dates can change; your specialist will confirm everything before you book.
