12 Inspiring Travel Challenges (For Each Month Of The Year)

Are you up for a challenge?

Let’s play a game:

You can make travel a bit more interesting than just checking attractions off a bucket list!

For example, let’s concentrate more on the experiences and the lessons learned than the places we see when we travel.

If you’re ready to take your travels to the next level, here are 12 travel challenges for you – one for each month of the year.

12 Travel Challenges

January: Riding The Last Narrow-Gauge Train In Bulgaria

What is a narrow-gauge train:

Narrow-gauge trains are a rare species. The 760-mm-wide rails aren’t used much anymore.

In Bulgaria, there’s just one line left, which runs on narrow rails. This is the track from Septemvri to Dobrinishte. It cuts through the magical Rhodope Mountains and the proud Pirin Mountain.

Narrow Gauge Train In Winter Travel Challenge January
The narrow-gauge train rides through the snowy hills of the Rhodope Mountains

Where can you ride one:

The most picturesque and awe-inspiring section of the journey is between the SPA Capital of the Balkans, Velingrad, and the highest train station on the Balkans, Avramovo.

Riding the narrow-gauge train is like time-machine travel.

The line was constructed between the 1920s and the 1940s. It seems like time has stopped in the villages whose train stations you pass. The ride is the most authentic glimpse into the lives of the people from the surrounding mountains.

How to conquer this travel challenge:

Buy your ticket at the Velingrad train station. It costs 2.60 lv (1.30 € or $1.50).

Alternatively, catch the train at Velingrad-South train station. There’s no office at this station, so you need to buy the ticket on the train.

After one hour, several 8-shaped serpentines, and tens of tunnels, the train will arrive in Avramovo. The ride back leaves in an hour.

Alternatively, you can take a taxi from Velingrad to Avramovo and ride the train just in one direction.

The narrow-gauge train runs several times a day. You can check the current timetable at any of the train stations.

Why should you do it in January:

In January, winter is in its heyday. The season’s fluffy, pure duvet covers the mountains and they look as taken from a children’s book.

The cold weather also adds an extra level of difficulty to your travel challenge. Getting your hiney a bit cold is a challenge you’re up to, right?

February: Walking Trunk In Hand With An Elephant Lady In South Africa

What is walking trunk in hand with an elephant:

This is simply the alternative to walking hand in hand with your buddy. Only in this travel challenge, your buddy is an elephant lady.

She puts her trunk in your hand and the two of you go for a walk.

Where can you walk with an elephant:

The Elephant Sanctuary near Plettenberg Bay on the Garden Route is home to rescued elephants. You should put it on your South Africa itinerary!

These South African animals were saved either from illegal private zoos or from the wild. They have been mistreated or suffered an injury.

Into the wild, they can’t make it on their own. In the sanctuary, they learn to live with each other and to take care of themselves.

Walking With Trunk In Hand With An Elephant Travel Challenge February
Walking trunk in hand with an elephant in South Africa in one of the best travel challenges you can conquer

For example, the lady on the photo above lost the tip of her trunk. This meant that she would starve to death as her trunk serves as a multi-purpose tool.

One of the functions of her trunk is to pick up food and place it in her mouth. With her severed trunk, she was unable to do so.

In the sanctuary, she learned how to suck in objects instead of picking them up. Now, she’s able to feed without external help.

How to conquer this challenge:

One (strange) thing I noticed in the sanctuary is this:

People are afraid of elephants.

And they should be!

The giant mammals have unpredictable behaviour. They might vandalise an entire forest just for the fun of it.

Standing near a one-tonne-heavy bully with the size of a small house is indeed scary.

Young Male Elephants
You better observe these young male elephants from a distance

However, if you overcome your fear, you’ll end up with one of the most amazing travel experiences of your life!

Simply hold your hand with the palm facing up and your elephant friend will place her trunk in it.

Then you’ll start walking and she’ll follow you.

It sounds so simple but it is the most extraordinary travel challenge I’ve ever conquered. And you should try it, too.

Why should you do it in February:

February is the shoulder season in South Africa.

There aren’t many tourists around and you wouldn’t have to wait long in line until your turn to walk trunk in hand with your new elephant friend comes.

March: Exploring A Snapshot Of The Past In Italy

What is a snapshot of the past:

Usually, when you visit ruins, you see what time has done to a city. Stones have fallen down, walls have been demolished, and you can’t fully imagine the grandeur of the place.

On the contrary, when you visit Pompeii, you’ll notice that it wasn’t time that destroyed the city.

Street in Pompeii
This street in Pompeii is almost intact

It was one single act of violence from nature, the eruption of the nearby Vesuvius Volcano, which wiped off all living creatures from the city.

In a matter of seconds, life Pompeii ceased to exist. However, the buildings, the streets, and the interiors survived the disaster.

Buried under a thick layer of ashes, the city of Pompeii kept most of its original appearance from the 1st century AD. Once archaeologists removed the ashes, they uncovered an almost untouched snapshot of the past.

Where can you find it:

The archaeological site of Pompeii lies near Naples, Italy. You can reach it easily by train, car, or bus.

You can admire the threatening sight of the active volcano from a distance or visit it after you’ve seen what it was capable of doing.

How to conquer this travel challenge:

Wear sturdy shoes if you decide to visit Pompeii. The cobble-stoned streets and the ruins of the city offer uneven pathways.

Moreover, if you also climb Vesuvius, you need to do a short but steep hike up the side of the volcano. The trail is covered in slippery stones and volcano ashes.

Honorary Arch Pompeii
One of the Honorary Arches in Pompeii with Vesuvius in the distance

Why should you do it in March:

As you might imagine, Italy’s landmarks receive hordes of tourists each year.

Luckily, the weather in March is still a bit cold for most travellers to spend a day outside, roaming the ruins of an ancient city. This is your chance to walk alone at least some of the back alleys of Pompeii.

April: Discovering Unexpected Attractions In Paris

What unexpected attractions can Paris possibly hide?

You can easily imagine that Paris is one of the most visited and touristy places on Earth. And you might be wondering if there’s anything unusual to do in Paris at all.

Surprisingly, even the most popular attractions keep unexpected secrets.

For example, when you hear The Louvre, in your head certainly pops up the image of the Mona Lisa.

But if you check the map of Louvre’s collections, you’ll discover that there are tonnes of equally exciting artefacts to explore in the largest museum in the world.

Where can you find unusual things to do in Paris?

You see, even the most famous museums hide surprising treasures.

So here’s a short but sexy list to inspire your search for unusual things to do in Paris:

  • The Louvre: find peculiar collections and marvel at the interior of the former palace.
  • Graveyards: pay respect to some of the greatest talents of the past in the Parisian cemeteries.
  • The Eiffel Tower: spy on Gustave Eiffel’s secret private apartment.
  • Parks: play with sailboats in the royal ponds.
  • Cabarets: discover the best of the Parisian nightlife.

How to conquer this challenge:

Unusual Art in the Louvre
How’s that for unusual art in the Louvre?

My best advice for Paris is to limit your stay to exactly three days.

Why only 3 days in Paris, when there’s so much to see and do in the French capital?

Because if you stay longer, you’ll start seeing the imperfections of the large city with hordes of tourists even in low season.

Because if you stay longer, you’ll push yourself to see more than your mind can take and walk further than your feet can carry.

Moreover, because if you stay longer, you might not want to return. And Paris is not a place to visit just once in your lifetime and never return to!

Why should you do it in April:

To avoid at least some of the tourist crowds, come in low season. Autumn and early spring is the best time.

Moreover, in April, the temperatures are pleasant for long strolls along the Seine River. The trees have some foliage and the parks look lovely.

May: Finding Secluded Paradise In The Dominican Republic

Where can you find seclusion:

Despite being best-known as an all-inclusive destination, the Dominican Republic still hides countless secluded beaches and unexplored jungles.

You can find seclusion on empty Dominican beaches.

You can descend into the depths of the Earth in one of the largest limestone caves in the area.

Cordillera Samana
The lush greenery of Cordillera Samana rolls into the Atlantic Ocean

Or you can explore the last secret gem of the Caribbean, the Samana Peninsula.

How to conquer this travel challenge:

The first step is to stray away from all-inclusive resorts.

Don’t be afraid to explore the vibrant Dominican Republic and search for its hidden gems. Be prepared and open-minded and you’ll end up with wonderful memories.

Ready for an adventure? Then read these travel tips to learn how to best explore safe and hassle-free.

Why should you do it in May:

Of course, you want to avoid visiting the island republic during the hurricane season. During the rest of the year, the weather is great for sunbathing and exploring the tropical paradise.

The months from December to April are the best time to visit. That’s why my recommendation is to pick May – shortly after the crowds have left – for your adventure in the Dominican Republic.

June: Conquering Europe’s Deepest Canyon On A Raft

Where is the deepest European canyon?

In the mountains of Bosnia and Herzegovina, runs the Tara River.

Known as the Colorado of the Balkans, the river has carved a fascinating canyon. It is deeper than any other in Europe. For comparison, the Grand Canyon is only slightly superior to this one.

Tara River Canyon Rafting Adventure
The rafts are waiting for you to conquer the Tara River Canyon

Between the Bosnian town of Foca and the border with Montenegro, you can raise your adrenaline in a surreal white-water rafting adventure.

How to conquer this challenge:

The turquoise waters of the Tara River canyon invite you to jump right in. You should be careful, though. The crystal waters might seem shallow, but the river is two to four metres deep!

Take part in a rafting adventure, organised by the skilful tour companies in the area. You can find small camps at the riverbanks along the road.

Why should you do it in June:

The neoprene suits provided by the rafting companies protect you from the refreshing waters of the river. However, once you come on shore, you need to shower and dry yourself.

Trust me when I tell you, it is not pleasant to do so when the temperatures are below 10°C (50°F).

On the other hand, later in summer you risk being eaten alive by mosquitoes.

This leaves June as the perfect month to indulge in this unforgettable rafting adventure.

July: Dancing The Night Away At The Black Sea Coast

What dances are we talking about:

This travel challenge is for the most hard-core and open-minded travellers.

Because you see, Bulgarian folk dances are also known as the Eighth Miracle. That’s how fascinating line dancing in Bulgaria is!

And once you’ve tried it and you’ve mastered the steps, you won’t stop until you can no longer stand on your feet.

Where can you dance the night away:

Visit the small villages at the Northern Bulgarian Black Sea Coast.

How to conquer this travel challenge:

There are just three easy steps to conquering this travel challenge:

  • Stay at a traditional guesthouse.
  • Make friends with everyone around.
  • Join the dances when the music starts.

Why should you do it in July:

I recommend July for two reasons.

  1. It is summer and you can combine the dances with some suntanning at some of the best Bulgarian beaches or enjoy sea kayaking around the rugged cliffs.
  2. If you arrive on the last day of June, you can witness the traditional July Morning festivities. They are a joyful celebration of new beginnings and positive thinking.

August: Surviving And Making Friends At The Roof Of The World

What is The Roof of the World:

The Pamir Mountains in Central Asia are a place of extremes.

Nothing grows on this Alpine desert at the altitudes of over 4,000 m (13,000 ft.). Inaccessible peaks rise twice as high.

Streams might freeze in mid-August and temperatures might drop lower than in Siberia and Alaska in winter.

Pamir Highway Near Karakul
The beauty of the Pamir Mountains and the kindness of its people make you forget the difficulties of this travel challenge

However, despite the harsh living conditions and possible language barriers, you meet some of the friendliest and kindest people in the world.

They invite you to their homes, share the little food they have with you, and most importantly tell you about their lives, dreams, and desires. You make friends for life and experience diverse cultures, which you can’t meet anywhere else on the planet.

Where should you travel:

To explore the Pamirs, you need to reach the ex-Soviet republics Tajikistan and Kyrgyzstan.

Getting to their capital cities is quite convenient. For Kyrgyzstan, most travellers don’t need visas. For Tajikistan, you can apply for an e-visa. When visiting the Pamirs, don’t forget to request a GBAO permit as well.

How to conquer this challenge:

You can drive, cycle, or even hitchhike the Pamir Highway. Take the road from Dushanbe (the Tajik capital) to Osh (the second largest city in Kyrgyzstan) or vice versa.

Of course, you are most flexible and safe with a guide and a driver.

Governments – past and present – have long forgotten the area in the two neighbouring ex-Soviet republics. The few roads, which were once paved, have more potholes than asphalt left.

The so-called Pamir Highway can hardly qualify as a speedway in any modern country. Instead, dusty roads take you to small villages without running water and electricity.

But if you’re up for a life-changing travel experience, this is your destination!

So pack light and warm, take your biggest smile and the friendliest attitude you’ve got, and you’ll end up with unbelievable stories to tell your grandchildren.

Why should you do it in August:

August is the driest month of the year in the Pamir Mountains.

This is extremely important because even a few raindrops can cause landslides and roadblocks, preventing you from having an adventure of a lifetime.

September: Greeting The Sun Over The Rock Forest Meteora

What is a rock forest:

Have you ever visited a place, which exceeded the boundaries of your imagination?

For me, one such place was Meteora, Greece.

The Meteora Rock Formations
The first sunrays of the day paint the Meteora Rock Formations in gentle pink

The high-rising boulders, some topped with levitating monasteries, form an incredible image. Nature and the human spirit have created scenery like no other.

Where can you find it:

Perched atop the cliffs, the Meteora Monasteries near Kalambaka in Central Greece welcome visitors all year round.

Follow the 7-kilometre-long scenic road and admire the surreal views of the rocks and the monasteries around you.

How to conquer this travel challenge:

There are just four steps to conquering this unforgettable travel challenge:

  1. Get up early. Use an app or ask the locals about the time of the sunrise. Dress warm, even in summer. The wind can be fierce. After all, it carved these mesmerising rock formations.
  2. Drive to the Meteora Rocks. Try to arrive about half an hour before dawn. There are several designated areas where you can position yourself and meet the new day.
  3. Greet the first sunrays. As they hit the rocks, their reflections paint the cliffs in gentle pink colours.
  4. Move on to the Great Meteoron Monastery. Listen to the sound of the bells calling for prayer.

Why should you do it in September:

The temperatures at the end of the European summer are more pleasant than at its zenith.

However, they’re still quite high – and you need them to be over 20°C. That’s because the winds, which have shaped Meteora Rock Formations, still blow harshly.

After all, if you get up in the middle of the night to greet the sun, you’d want to feel at least some comfort.

October: Tasting Slow-Food Exquisite Delicacies In Ireland

What is slow food:

You know how we’ve become obsessed with time and getting things done quickly? Even when we eat, most of us prefer the so-called fast food to save some extra minutes.

However, that’s not only unhealthy but it’s unpleasant and boring.

Food should be devoured slowly, each bite should be enjoyed, and each aftertaste should be appreciated.

Seafood Chowder
The award-winning Seafood Chowder of Beara Coast Hotel’s chef

That’s what the slow food culture is all about. Taking time to make a perfect dish and then savouring each moment tasting it.

Where can you taste it:

The Beara Peninsula in Ireland, albeit not as famous as other regions of the island, is home to local producers who keep ancient recipes. They take the time and effort to produce delicacies, which will make your palate cry with joy.

How to conquer this challenge:

These are some of the places where you can devour Beara’s exquisite treats:

  • The award-winning seafood chowder at the Beara Coast Hotel.
  • The Beara Ocean gin with water from the Atlantic Ocean at the Beara Distillery.
  • The Irish farmhouse raw-milk cheese at the Milleens Cheese.
  • Locally farmed mussels at the Kush Shellfish Restaurant.

Why should you do it in October:

There’s something magical about the countless shades of green in Ireland. Combined with the radiant autumn foliage of the trees in October, you’ll experience more colours than your eyes can distinguish.

Check also this 7 days Ireland road trip itinerary to make sure you don’t miss the most magical spots on the Emerald Island.

November: Chasing The Last Summer Days On The Cyprus Beaches

Where can you find the best Cyprus beaches:

The Cypriot coastline is predominantly rocky with rugged cliffs rising up like scary guardians. The Mediterranean Sea and the harsh winds have sculptured jaw-dropping arcs and bottomless caves.

The Best Cyprus Beaches
A stunning sunset over a Cypriot beach

Nevertheless, if you know where to search, you’ll find amazing beaches to work on your tan as well.

How to conquer this travel challenge:

Here are the steps to follow:

  1. Follow the map and visit as many of the numerous Cyprus beaches as possible.
  2. Suntan and stock on vitamin D whenever the temperatures allow it.
  3. Explore the countless ancient ruins on the Mediterranean island when not on the beach.

Why should you do it in November:

As with other popular destinations, it’s key to visit Cyprus when the crowds have already left. Moreover, you should do it before winter. The winds, which have shaped the rugged coastline, are fierce.

Hence, November is your last chance before spring to sunbathe or even swim anywhere in Europe.

December: Uncovering The True Spirit Of Christmas

What is the true spirit of Christmas:

In my humble opinion, the true spirit of Christmas doesn’t come from exchanging expensive presents with your loved ones but from spending precious time with them.

Christmas Market - Dresden
One of the most famous Christmas markets in Germany is in Dresden

In the dull, winter days, what better place to spend a few hours and enjoy the bright decorations than a German Christmas Market!

Where can you find it:

Germany is home to some of the oldest and most joyful Christmas traditions in the world.

Every square in every town, every castle or fortress, every farm and every community organise their own Christmas market. Although the size and splendour can vary greatly, there are fun things to do and nice memories to be made at every Christmas market.

Still, the most famous Christmas markets in Germany are in the following cities:

  • Nuremberg,
  • Dresden,
  • Berlin,
  • Cologne,
  • Dusseldorf,
  • Dortmund,
  • Frankfurt,
  • Munich.

How to conquer this challenge:

For the best possible results, go on a Christmas market hopping tour!

German Christmas Markets Travel Challenge December
A vendor selling grilled sausages and steaks and a Christmas pyramid with a Glühwein bar in Dortmund

Either in a German city you’re visiting, or through a larger area, don’t limit yourself to just one German Christmas market. The magic is in the variety and the different themes of the markets.

Which Of The Travel Challenges Will You Do Next?

There are no winners at this game. There are no prizes either.

Only the countless memories and the good friends you make along the way.

Isn’t this what travel is all about?

I hope you’ll enjoy all of the travel challenges on this list. Don’t forget to share, which one is your favourite!

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