Epic country crossing challenge holidays
Traversing a country, whether coast to coast or border to border, gives you a great insight into its consistencies and contrasts. The chance to examine a country by its cross-section will give you a really good idea of what it's like. It can also present a fun fitness challenge holiday. Whether you tackle your traverse by bike, foot, kayak or with a trusty steed, here are our epic country crossing challenge holidays.
20 Epic country crossing challenge holidays found
Douro valley by kayak holiday, across Portugal
Kayak across Portugal on the Douro River
From €3,370 10 days ex flights
Small group travel:
2026: 25 Sep
2027: 26 Feb, 21 May, 24 Sep
2027: 26 Feb, 21 May, 24 Sep
£400 discount available on our September 25th group departure, book soon to secure your space.
Trek the GR20 of Corsica
Walk the challenging GR20 from Conca to Calenzana
From £3,679£3,319 to £3,929 15 days ex flights
Small group travel:
2026: 29 Aug
2027: 17 Jul, 31 Jul, 28 Aug
2027: 17 Jul, 31 Jul, 28 Aug
Up to £360 off selected dates.
Late availability on these dates: 29 Aug
Late availability on these dates: 29 Aug
Trans Wales trail running holiday
Travel border to beach on this long-distance running holiday
From £945 5 days ex flights
Small group travel:
2026: 17 Sep
Trans Montenegro cycling tour
Cycle Durmitor mountains, Lake Skadar & the Bay of Kotor
From €1,070 to €1,170 8 days ex flights
Tailor made:
This trip can be tailor made throughout the year to suit your requirements
Cycle Montenegro, Bosnia and Albania and in autumn: mild temperatures, golden vineyards, quiet coastal roads, and clear mountain views over Kotor Bay. Fewer crowds, cooler climbs. Explore, experience & enjoy something new!
Contact Us
Call us for a chat about our holidays. We are happy to discuss your holiday and help in any way we can. No bots, queues or awful hold music.
01273 823 700
Call us tomorrow after 9am
Calling from outside the UK
rosy@responsibletravel.com
Sri Lanka coast to coast cycling holiday
Sri Lanka Coast to Coast Cycling: Temples Jungles Beaches
From US $1,965 13 days ex flights
Tailor made:
This trip can be tailor made throughout the year to suit your requirements
South India cycling tour, coast to coast
South India Coast to Coast cycling Holiday
From US $2,480 14 days ex flights
Tailor made:
This trip can be tailor made throughout the year to suit your requirements
East Cape to Cape Egmont cycle tour, New Zealand
1100km cycle route East Cape to Cape Egmont
From NZ $5,200 15 days ex flights
Small group travel:
2026: 11 Nov
Great Himalaya Trail trek across Nepal
The ultimate adventure across Nepal on a 150 day trek
From £25,990 150 days ex flights
Small group travel:
2027: 10 Mar
North Coast 500 cycling tour in Scotland
Fully supported cycling the Scottish North Coast route 500
From £1,695 to £1,795 7 days ex flights
Small group travel:
2026: 5 Sep
2027: 21 Aug
2027: 21 Aug
Chennai to Kochi cycling holiday, India
Coast to coast Southern India cycling tour
From US $2,560 to US $2,930 16 days ex flights
Small group travel:
2026: 1 Nov, 16 Nov, 20 Dec
2027: 17 Jan, 7 Feb, 27 Feb
2027: 17 Jan, 7 Feb, 27 Feb
South Island bike packing adventure, New Zealand
Cycle Marlborough to Milford across the Southern Island
From NZ $10,800 21 days ex flights
Small group travel:
2027: 1 Mar
England road cycling holiday, coast to coast
Best road cycling in England, ride coast to coast
From £3,491 0 days ex flights
Small group travel:
2027: 16 May, 13 Jun, 1 Aug, 5 Sep
England coast to coast walking holiday
Travel the width of England on foot, coast to coast
From £4,909 to £5,049 13 days ex flights
Small group travel:
2026: 4 Oct
2027: 9 May, 20 Jun, 1 Aug, 12 Sep
2027: 9 May, 20 Jun, 1 Aug, 12 Sep
Late availability on these dates: 04 Oct
Cycle the North Island, Cape Reinga to Wellington
Cycle the length of the North Island, New Zealand
From NZ $10,200 21 days ex flights
Small group travel:
2027: 15 Feb
Contact Us
Call us for a chat about our holidays. We are happy to discuss your holiday and help in any way we can. No bots, queues or awful hold music.
01273 823 700
Call us tomorrow after 9am
Calling from outside the UK
rosy@responsibletravel.com
Cycle the whole of New Zealand
Cycle New Zealand North to South fully supported
From NZ $19,600 6 weeks ex flights
Small group travel:
2027: 15 Feb
Hadrian’s Wall Trail walking holiday, England
83 miles/133 km across town and country, forest and moorland
From £790 8 days ex flights
Tailor made:
The trip can be booked betwen April and mid October
Border to coast horse riding holiday in Wales
This is a real trail riding expedition, covering 100 miles
From £2,885 6 days ex flights
Small group travel:
2026: 8 Sep
Cycling tour across Borneo
Epic Trans-Borneo Ride End-To-End
From MYR22,500 15 days ex flights
Small group travel:
2026: 1 Nov
Cycle the length of Portugal
Cycle Portugal North to South fully supported
From £1,745 to £1,795 9 days ex flights
Small group travel:
2026: 26 Sep
2027: 17 Apr, 25 Sep
2027: 17 Apr, 25 Sep
Lands End To John O'Groats cycling trip
Britain's classic cycling challenge
From £2,695 to £2,795 16 days ex flights
Small group travel:
2026: 5 Sep
2027: 4 Sep
2027: 4 Sep
