Top 10 epic country-crossing challenges

Can you really get under the skin of a destination on holiday? Whilst it can take years to get the lay of the land in a country, traversing a nation gives you a compelling cross section of life there, and how it changes between towns and cities and between the countryside and coast. Not only do you get a great sense of place in these top 10 country-crossing challenges, but a great sense of achievement, too, for doing it under your own steam. If nothing else, you’ll come away with muscle memory of a country's topography!

1. Cycle coast to coast across Costa Rica

On two wheels you can make short work of the Central American isthmus – at its narrowest point, Costa Rica is just 120km across. So why stop there? Instead, choose a tour of the country that goes a bit further, including time off the bike for Manuel Antonio National Park, a boat trip in Tortuguero and Arenal Volcano. With a support vehicle on hand for some of the steeper hills, and plenty of tempting roadside cafés among the wealth of wildlife, Costa Rica is enjoyable both in and out of the saddle.

Best time to go: All year round
Our top trip: Coast-to-coast cycling holiday in Costa Rica
See all our trips: Costa Rica cycling holidays
Read more: Costa Rica cycling guide

2. Kayak across Portugal via the River Douro

Whilst centuries of settlement in the Douro wine region have carved the steep hills around the river into a wavy staircase of terraces, it cannot fully tame the Douro River itself, which runs from Spain through Northern Portugal and enters the Atlantic Ocean at Porto. A series of dams have made the river safe and navigable, but it still retains its natural beauty. You can kayak downstream from Pocinho, near the Spain border, all the way to Porto. The trip is comfortably undertaken over seven days on the water. You’ll pass grand old quintas – wine estates – but you won’t be able to pass all of them by without stopping for a tasting or two.

Best time to go: All year round
Our top trip: Douro Valley by kayak holiday, across Portugal
See all our trips: Portugal holidays
Read more: River kayaking guide

3. Take on the Great Himalaya Trail

You don't need to be an expert mountaineer to give Nepal your all, yet walking the Great Himalaya Trail is a feat comparably epic to summitting one of its mountains. If you're not short on time or cash, then you can do the whole of this mammoth route across Nepal – an extraordinary 150-day, 1,700km-long journey. The journey connects some of the highest passes in the Himalayas and the most popular walking regions in Nepal, passing Kanchenjunga, Makalu, Everest and Annapurna. With less time, you could opt to hike a section. Once you know that this trip exists, it's hard to stop thinking about it.

Best time to go: February
Our top trip: Great Himalaya Trail trek
See all our trips: Long distance walking holidays
Read more: Great Himalaya Trail guide

4. Run across Wales

Putting the cross-country running into country-crossing: if you like jogging, why not swap your pavement-pounding for the spongy grass and rocky ridges of mid-Wales? It’s 88km from the Borderlands to coastal Aberystwyth via a route through the little-visited Cambrian Mountains. If you can run for four to five hours continuously – and get out of bed on three consecutive days to do so – then this challenging tour is within your reach. You’ll be in safe hands with an experienced trail runner leading the way.

Best time to go: spring or autumn
Our top trip: Trans Wales trail running holiday
See all our trips: Fitness holidays
Read more: Trail running guide

5. Cycle the whole of New Zealand

Cycling down both North and South Island in New Zealand – with the help of a couple of ferries – will set you back 2,950km and take around six weeks. Cycling is mostly done off roads, on a network of cycle trails that are used for the Tour Aotearoa, to better get close to the spectacular scenery for which New Zealand is known. Somewhere between ducking under massive ferns on the Timber Trail and freewheeling down the West Coast Wilderness Trail, you’ll be completely seduced by the natural landscape. Deciding which island you preferred afterwards? Impossible.

Best time to go: February
Our top trip: Cycle the whole of New Zealand
See all our trips: New Zealand holidays
Read more: Guide to the Tour Aotearoa

6. Tackle the Trans Bhutan Trail

The Trans Bhutan Trail – originally a network of trails – was once the only way to get a message across the Himalayan country, a place where travel is complicated by massive mountains, and where there’s still only one main road. The trail fell out of use when the road came in, but has now reopened for trekkers, thanks to the tireless efforts of a local social enterprise with the unenviable job of restoring 12,000 steps. The trail links 27 villages and the country’s capital on its route from Haa to Trashigang. A full through-hike along the 403km route will take a month, but this wonderful path can be accessed at different points, meaning that you could always do a section – as a Trans Bhutan Taster.

Best time to go: October
Our top trip: Trans Bhutan Trail walking holiday
See all our trips: Bhutan tours
Read more: Trans Bhutan Trail

7. Cross Borneo by bike

Cycling is growing in popularity in Malaysia, but few consider taking two wheels to Borneo. Yet if you can handle a bit of humidity and hills, road cycling here is fantastic. Over 12 days you’ll cover 1,370km and cross from Malaysian Borneo into Brunei – and back again – resulting in eight additional stamps in your passport. On the way, there are plenty of places to explore out of the saddle: from hunting for monkey sightings in national parks to exploring Bandar Seri Begawan, the capital of Brunei. A beachside rest day and a spot of foot reflexology comes at exactly the right time – before a challenging multi-day ascent to the basecamp of Kota Kinabalu.

Best time to go: October-December
Our top trip: Cycling tour across Borneo
See all our trips: Borneo cycling holidays
Read more: Borneo cycling guide

8. Go horse riding across Wales

Gone are the days when you could stop at an inn and hand your reins over to a trusty ostler for the night. Nowadays, setting up a horse ride across Wales takes careful logistical planning. Thankfully, our partners can do all that for you. You’ll be in charge of feeding, grooming and tacking up your trusty steed, before heading on the trail for the five days it takes to cross from the Wye Valley to Ynyslas via the Cambrian Mountains. Horses get dropped off each night with local farmers, whilst you can stay in town. A celebratory canter along the beach is a fitting finale on the last day.

Best time to go: April to October
Our top trip: Border to coast horse riding holiday in Wales
See all our trips: Horse riding holidays
Read more: Horse riding travel guide

9. Try peninsular India on two wheels

It takes one hour to fly, 15 hours to drive, but by bike you can stretch a trip across peninsular India into two fascinating weeks, exploring the states of Tamil Nadu and Kerala. Cycle up through sandalwood forests in the cardamom hills, past tea plantations and hill stations and down to the beach again – this trip is a great way to see which side of the country has the best coastline (it might just be the west). You won’t be the only cyclist – cycling is rising in popularity – but you’re probably going the furthest.

Best time to go: November to March
Our top trip: South India cycling tour, coast to coast
See all our trips: India cycling holidays
Read more: Cycling in India travel guide

10. Enjoy England’s coast-to-coast walk on foot

If you’re going to do things properly on England’s Coast to Coast Walk, you have to start by standing in the Irish Sea at St Bees with your boots on, and then end this 222km walk doing the same in Robins Hood’s Bay, on the North Sea – that’s how Alfred Wainwright, the fell walker and writer who designed this trail, did it. There are plenty of other tales to tell on this route, which passes through the varied landscapes of the Lake District, Yorkshire Dales and Yorkshire Moors over 13 days, following the footsteps of Romantic poets, stopping for a traditional cream tea or a pub lunch, and passing atmospheric ruined abbeys – it’s a historic English journey that’s worth a bit of salt on your shoes.

Best time to go: April to October
Our top trip: England coast-to-coast walking holiday
See all our trips: England walking holidays
Read more: England walking travel guide
Written by Eloise Barker
Photo credits: [Page banner: Raimond Klavins] [1. Cycle coast to coast across Costa Rica: Marissa Strniste] [4. Run across Wales: Greg Rosenke] [7. Cross Borneo by bike: Rio Bahtiar] [10. Enjoy England’s coast-to-coast walk on foot: Candy Goode]