20 of the World’s Most Outrageous Travel Challenges: Do You Dare?

1. Running the Marathon Des Sables

Taking on the Marathon des Sables is more than just a race; it’s a bold adventure where you push your limits across the Sahara, the largest hot desert in our world.

Race over 250 kilometers in six days, across a landscape that’s as breathtaking as it is brutal. The heat is intense, often soaring above 50°C (122°F), and the desert terrain changes under your feet—from sand dunes to flat plains.

You’ll carry everything you need on your back, which means packing smart is crucial. It’s not only about physical strength; it’s a mental game too. The solitude of the desert can be both calming and testing.

2. Sailing Around the World Solo

The Global Solo Challenge is an epic event where sailors navigate the globe single-handedly, kicking off from Spain and could stretch over months.

Cole Brauer is an American woman setting records in this daring feat, proving the ocean’s might and our human resilience. Accomplishments like hers, achieved in the 2023/2024 challenge inspire many.

3. Visiting Every Country Without Flying

If you’ve ever thought about setting a remarkable travel goal, consider this: traveling to every country in the world without ever boarding a plane. It’s not just a hypothetical idea—some adventurers have actually embarked on this epic quest.

A notable example is Torbjørn “Thor” Pedersen, who took on the globe by land and sea, with a dedication to cross all international borders without the aid of flights.

4. The Tomatina Festival

Every year, the town of Buñol in Spain turns vibrantly red as thousands come together for La Tomatina. Dive into a sea of ripe tomatoes, armed and ready for the world’s largest tomato fight.

Armed with goggles and old clothes, you’ll join excited participants under the Spanish sun. At the signal, the air fills with flying tomatoes, and Buñol’s streets become rivers of red. It’s a good-natured battle where the laughter competes with the splats of tomatoes hitting their targets.

5. Swimming Across the English Channel

Have you ever dreamed of swimming between two countries? The English Channel is a stretch of water that separates Southern England from Northern France. Adventurous souls take on the challenge to swim the 21 miles from Dover to Calais.

The swim is not just about distance, but also tackling strong tides and chilly waters. With temperatures averaging 15°C (59°F), endurance and preparation are key. In 2019, Sarah Thomas made marathon swimming history by completing a four-way crossing, a phenomenal achievement.

Australian marathon swimmer Chloe McCardel took it further, notching up her 44th crossing. You could be next! It requires training, determination, and a support team. Ready for the plunge?

6. Hiking the Pacific Crest Trail

The Pacific Crest Trail stretches a massive 2,650 miles from Mexico to Canada through California, Oregon, and Washington. It’s a formidable challenge that requires preparation and commitment, but the rewards are immense.

Hiking the PCT isn’t just a walk in the park – it’s an epic journey through scorching deserts, over snow-covered mountains, and through lush forests!

7. The Baby Jumping Festival

In the heart of Castrillo de Murcia, Spain, you can witness a spectacle that’s as fascinating as it is peculiar—the Baby Jumping Festival. Held annually, this event intertwines religion and local tradition in a ceremony where men, donned as devils, leap over infants.

This isn’t just for show; it’s believed to cleanse the babies’ souls, shielding them from future misfortune.

8. Biking The Death Road

Embarking on a bike ride down Bolivia’s notorious Death Road is not just a pedal through the park—it’s a thrilling challenge that will have your adrenaline soaring. This narrow road carved into the mountainside is famous for its breathtaking cliffs and spectacular views.

Your journey begins high in the Andes and descends nearly 3,600 meters to the lush Amazonian rainforest, making it a dramatic shift in terrain and climate. Some stretches lack guardrails, and the unpaved sections demand focus.

9. The Rickshaw Run Across India

Embarking on the Rickshaw Run is like turning the pages of an adventure book where you’re the hero. Picture yourself zipping through India’s vibrant landscape in a motorized rickshaw!

You’ll navigate through chaotic traffic, dodge wandering cows, and find your way on roads less traveled. Your rickshaw isn’t just a vehicle; it’s your companion on a 3,000 km journey where every turn is a new chapter. And it’s all for a good cause, with teams often raising money for charity.

10. Cycling The Tour D’Afrique

Embarking on the Tour d’Afrique is a test of endurance and a way to connect deeply with Africa’s diverse landscapes. You’ll pedal over 11,000 km from the bustling streets of Cairo to the stunning vista of Cape Town.

Your journey takes you through 10 countries, across deserts, past ancient monuments, and through bustling marketplaces. It’s not just a physical challenge; it’s a chance to meet locals, taste regional cuisines, and see wildlife most only witness on screen.

The route lasts around four months, with accommodation varying from hotels to camping under the stars.

11. The Mongol Rally

The Mongol Rally is a wild car adventure across continents, from bustling cities to the vast, open spaces of the Mongolian steppe. Starting in Europe and ending in Ulan Ude, the course spans around 10,000 miles.

Select a car with an engine no bigger than 1.0 litre—part of the challenge—and prepare for the sights, sounds, and cultures of 20 different countries.

Your Mongol Rally adventure isn’t a guided tour; there is no set route. This freedom means it’s your strategy, your choices, and your story. But be wise: teaming up can turn tricky situations into shared triumphs.

12. The Iditarod Trail Sled Dog Race

With the Iditarod Trail Sled Dog Race, you’re not just a spectator; you’re in the heart of the action, pushing your limits across 1,000 miles of untamed wilderness.

Each March, mushers from all corners of the globe converge to compete with their teams of dogs through frozen forests, up daunting mountains, and across wind-swept tundra.

Your journey starts in Anchorage, and the finish line lies in Nome. Between start and finish, each checkpoint brings its own challenges. Prepare for unpredictable weather, from biting cold to blizzards.

13. Kayaking The Amazon River

Kayaking the entire length of the Amazon River could be your next big challenge. Covering about 4,300 miles, it’s an extraordinary journey from the high Andes in Peru all the way to the Atlantic Ocean in Brazil.

Darcy Gaechter is the first woman to complete this mammoth paddle, proving it’s possible with determination and grit. Along the way, anticipate paddling through serene waters and adrenaline-pumping rapids.

14. Climbing Mount Kilimanjaro

Climbing Mount Kilimanjaro is a true test of will and endurance. Reach the peak of Africa’s tallest mountain, not just for bragging rights, but for the sense of achievement that comes with it.

Rising majestically above the Tanzanian savannah, Kilimanjaro welcomes you with diverse landscapes, from lush rainforests to arid deserts. Your journey scales through five climate zones—each offering its own challenges and visuals.

15. Diving Between Continental Plates

Have you ever wanted to swim where the Earth pulls apart? Silfra Fissure in Iceland offers a unique dive between two tectonic plates. Glide through crystal-clear spring water in the gap between North America and Eurasia.

Visibility extends over 100 meters! This natural wonder awaits in the beautiful Thingvellir National Park. It’s chilly, but with a drysuit provided by local dive shops, you’ll stay cozy.

16. Walking Every Street in NYC

Some adventurous souls have actually accomplished this staggering feat. For instance, take the journey of Maya Gonzales Berry, who traversed 640 miles to cover each Manhattan street.

In an even more ambitious endeavor, Matt Green spent six years walking every street in all five boroughs of New York City!

17. Trekking To Everest Base Camp

Embarking on the Everest Base Camp Trek is like no other adventure you’ve had before. Breathing in the crisp Himalayan air, you’ll journey through the heart of the world’s most famous mountain range.

Starting with a scenic flight to Lukla, your trek unfolds across rugged trails, surrounded by towering peaks and vibrant Sherpa culture. The path leads you 65 kilometers from Lukla to Mount Everest Base Camp, a challenge that’s both physical and mental.

18. The Exploding Hammer Festival

You might think festivals are all about music and food, but wait until you hear about San Juan de la Vega’s Exploding Hammer Festival.

Just picture it: a crowd of people, excitement in the air, and then—bang! Hammers burst into a ground-shaking explosion. This unique tradition happens every Shrove Tuesday, marking a local revolt from the 17th century.

Participants strap a mix of sulfur and chlorate to sledgehammers and slam them against rail beams to create a thunderous display. With smoke and cheers filling the air, you’re sure to feel the community’s spirit.

They do this to honor San Juantito, a local hero, and the result is nothing short of amazing.

19. Crossing The Darien Gap

The Darien Gap is more than just an adventure; it’s a formidable stretch for any seasoned traveler. You’ll navigate through 66 miles of terrain where roads don’t exist. This part of the journey is known for its dense jungle and rivers that demand respect. While crossing, you might encounter everything from mud to wildlife, which includes dangers like venomous snakes.

20. The Cheese Rolling Festival

If you’re looking for a quirky travel challenge, the Cooper’s Hill Cheese-Rolling event is a must-try. Every year on the Spring Bank Holiday, thrill-seekers gather in Gloucestershire for a dash down a steep hill, chasing a wheel of Double Gloucester cheese.

The cheese gets a one-second head start and can reach up to 70 mph—so it’s really about crossing the finish line first. With a tumbling descent, you’ll need quick feet and a strategy to stay upright!