Epic country crossing challenge vacations
Traversing a country, whether coast to coast or border to border, gives you a great insight into its consistencies and contrasts. It can also present a fun fitness challenge vacation. Whether you tackle your traverse by bike, foot, kayak or with a trusty steed, here are our epic country crossing challenge vacations.
21 Epic country crossing challenge vacations found
Douro valley by kayak vacation, across Portugal
Kayak across Portugal on the Douro River
From €3,370 10 days ex flights
Small group travel:
2027: 26 Feb, 21 May, 24 Sep
Trans Wales trail running vacation
Travel border to beach on this long-distance running holiday
From £945 5 days ex flights
Small group travel
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
2028: 4 Feb, 17 Feb
2028: 4 Feb, 17 Feb
South Island adventurous cycling vacation, New Zealand
Cycle Marlborough to Milford across the Southern Island
From NZ $10,800 21 days ex flights
Small group travel:
2027: 4 Mar
2028: 4 Feb, 4 Mar
2028: 4 Feb, 4 Mar
Contact Us
Call us for a chat about our vacations. We are happy to discuss your vacation and help in any way we can. No bots, queues or awful hold music.
1-866-821-6866
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Calling from outside the USA
rosy@responsibletravel.com
Trek the GR20 of Corsica
Walk the challenging GR20 from Conca to Calenzana
From US $6,075 15 days ex flights
Small group travel:
2027: 17 Jul, 31 Jul, 28 Aug
Portugal N2 guided cycling tour
Cycle Portugal's N2 route from Chaves to Faro
From €2,200 to €2,500 8 days ex flights
Small group travel:
2027: 21 Apr, 26 May, 22 Sep, 5 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
East Cape to Cape Egmont private cycle tour, New Zealand
1100km east to west across the North Island
From NZ $5,200 15 days ex flights
Tailor made:
This trip can run throughout the year to suit requirements
Transcaucasian Trail walking holiday, Georgia
Small group hiking adventure to the mountains of Georgia
From US $2,690 11 days ex flights
Small group travel:
2027: 1 Jun, 17 Jun, 13 Jul, 10 Aug, 7 Sep, 21 Sep
Great Himalaya Trail trek across Nepal
The ultimate adventure across Nepal on a 150 day trek
From US $37,150 150 days ex flights
Small group travel:
2028: 8 Mar
Trans Montenegro cycling tour
Cycle Durmitor mountains, Lake Skadar & the Bay of Kotor
From €1,070 to €1,270 8 days ex flights
Tailor made:
This trip can be tailor made throughout the year to suit your requirements
Sri Lanka coast to coast cycling vacation
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
Portugal cycling vacation, north to south
Cycle Portugal famous N2 route 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
North Coast 500 cycling tour in Scotland
Fully supported cycling the Scottish North Coast route 500
From £1,795 7 days ex flights
Small group travel:
2027: 21 Aug
Contact Us
Call us for a chat about our vacations. We are happy to discuss your vacation and help in any way we can. No bots, queues or awful hold music.
1-866-821-6866
Call toll free
Calling from outside the USA
rosy@responsibletravel.com
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
Chennia to Kochi cycling vacation, 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
England road cycling vacation, 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 vacation
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
Hadrian’s Wall Trail walking holiday, England
83 miles/133 km across town and country, forest and moorland
From US $1,560 8 days ex flights
Tailor made:
The trip can be booked betwen April and mid October
Cycling tour across Borneo
Epic Trans-Borneo Ride End-To-End
From MYR22,500 15 days ex flights
Small group travel:
2026: 1 Nov
Lands End To John O'Groats cycling trip
Britain's classic cycling challenge
From £2,795 16 days ex flights
Small group travel:
2027: 4 Sep
