Travel isn’t always sunsets and scenic views—it can throw unexpected challenges our way. To uncover the untold side of adventures, I reached out to 13 seasoned travel writers to share their most challenging travel experiences.
These writers are no strangers to adventure, with years of globetrotting and storytelling under their belts. From navigating foreign customs to surviving extreme weather, their diverse stories highlight resilience and resourcefulness.
In this post, you’ll find gripping tales of perseverance, lessons learned on the road, and practical insights for overcoming travel hurdles. Whether you’re an avid explorer or planning your first trip, these stories will inspire and prepare you.
Nervous about the challenges of traveling? Read on to discover how these experts overcame their toughest moments—and how you can, too!
Feuza (aka Fuse): Brazilian-Born Travel Blogger and Content Creator from Fuse Travels
Bio:
Feuza, known as Fuse, is the voice behind Fuse Travels, a blog dedicated to stress-free, mid-budget European adventures and slow travel experiences. A Brazilian-born storyteller based in South Florida, she combines 16+ years of photography expertise with a passion for local culture, cuisine, and off-the-beaten-path destinations. As a contributing editor for Living in Italy Magazine and a member of the International Food, Wine & Travel Writers Association, Feuza inspires adventurers to explore authentically while sharing vibrant insights from her travels.
Response:
"One of the funniest and most challenging travel experiences my husband and I had was during a trip to Sintra, Portugal. I’d booked the train to Sintra but forgot to arrange transportation to the iconic Pena Palace. Once there, we were met with a decision: a long line for the bus or a more affordable private driver who was pressed for time due to a tour he was running. We chose the driver, who told us about a shortcut hiking trail we could use to get back down—it was supposedly a quick, 20-minute walk.
Well, that 'shortcut' turned into a 45-minute adventure! My husband and I aren’t hikers, and the path was anything but straightforward, with winding sections, inclines, and descents. Sweaty and slightly exasperated, we just kept laughing at the situation. I even filmed parts of it for posterity!
When we finally made it back down, we rewarded ourselves with a well-earned beer at a local restaurant and laughed some more at the unexpected adventure."
Key Takeaway:
Even the best-laid plans can lead to unexpected detours. Whether it’s a missed detail or an unforeseen challenge, a sense of humor can turn a mishap into a cherished memory.
A Year Stranded in Cape Verde: Patience and Community
Paulina from Visit Southern Spain
Bio:
Paulina is the founder of Visit Southern Spain, a travel website dedicated to uncovering the beauty and culture of Andalusia. With years of experience in the travel and event industry, and having lived in cities like Seville, Malaga, and Madrid, Paulina brings unparalleled expertise to her work.
Through Visit Southern Spain, she shares in-depth travel guides, insider tips on accommodation and transport, and insights into the region’s rich history and traditions. Fluent in Spanish and a regular visitor to Andalusia, Paulina’s passion shines in her coverage of local events like Semana Santa and Feria. Her platform is a go-to resource for travelers seeking to experience Andalusia’s unique cultural blend and vibrant heritage.
Response:
"One of the most challenging experiences I’ve faced was getting stranded on the remote Cape Verdean island of Maio during the COVID border closures. What began as a situation ripe for panic turned into a transformative year-long lesson in patience, resourcefulness, and the incredible power of community.
I was locked down for a year, but instead of succumbing to the anxiety of the situation, I embraced the opportunity to adapt. I found myself forging unexpected connections with locals, learning to live simply, and discovering the island’s unique beauty and culture.
Remarkably, this detour also became pivotal for my career. Forced to branch out, I explored new opportunities and grew in ways I never anticipated. Looking back, it was a great, life-changing experience—one I wouldn’t trade for anything."
Key Takeaway:
Even in the face of adversity, embracing the moment and leaning into the strength of community can lead to transformative personal and professional growth.
From San Sebastián to Madrid, pinchos are a must-try culinary experience—find out what makes them special in our Pinchos: Spain’s Bite-Sized Delights.
Lost Luggage in Prague: A Lesson in Preparedness
Kylee from Passports and Preemies
Bio:
Kylee Nelson is a Neonatal Intensive Care Unit (NICU) travel nurse and the creator of Passports and Preemies, a platform dedicated to empowering nurses to explore travel nursing opportunities and combat burnout. As a seasoned travel nurse, Kylee takes on new assignments every 13 weeks, sharing her experiences and expertise to inspire healthcare professionals to step outside traditional settings.
Through her blog, podcast (Passports and Preemies Talks), and thriving social media presence, Kylee offers tips on travel nursing, stories from the road, and encouragement for solo adventures. Her platform also features group trips designed specifically for nurses seeking connection and rejuvenation.
A solo travel enthusiast, wine lover, and Taylor Swift fan, Kylee combines her passions to create a vibrant community where nursing and travel intersect, inspiring others to find balance and joy in their careers.
Response:
"My first visit to Europe—Prague—was a trip I’ll never forget, and not just because of the city’s charm. Upon arrival for my 10-day trip, I discovered my checked luggage hadn’t made it with me. For three days, I wandered the city in the same clothes I had traveled in!
While it was inconvenient at the time, it taught me a valuable lesson: always pack a change of clothes in your carry-on when traveling internationally. It’s a simple habit that has saved me from similar mishaps ever since."
Key Takeaway:
Preparation is key when traveling internationally. A small backup plan, like a change of clothes in your carry-on, can save the day when the unexpected happens.
Cross-Border Challenges: Navigating Spain and Portugal by Car
Jennifer from Sidewalk Safari
Bio:
Jennifer, known as Dr. J, is the travel blogger and content creator behind Sidewalk Safari, a website specializing in detailed travel tips and itineraries for European destinations. With a focus on road trips and practical advice, she helps travelers navigate countries like Portugal and Spain with ease and confidence.
Her expertise shines through in comprehensive guides that include transportation tips, cultural insights, and destination-specific advice. Known for her meticulous approach, Dr. J crafts resources like The Ultimate 2-Week Portugal & Spain Christmas Road Trip, offering travelers expertly planned routes and tips for cross-border adventures.
Through Sidewalk Safari, Jennifer shares her passion for European travel, empowering readers to explore with confidence and uncover hidden gems along the way.
Response:
"I live in Portugal, and like many who visit the region, I love doing road trips that span both Portugal and Spain. Normally, I prefer using trains and buses, but the transit connections between the two countries are slow and inconvenient.
To overcome this challenge, we often hire a car. It’s the best solution, providing flexibility and convenience. However, there are some pitfalls to be aware of. If you rent a car in Portugal, you’ll likely be charged a cross-border fee, which can exceed €50 depending on the rental car company, the car class, and the length of your reservation. Trips originating in Spain are less likely to incur this fee.
One crucial tip: always declare your intent to cross the border to your rental car company. This prevents unwelcome surprises that could derail your trip!"
Key Takeaway:
When traveling between Portugal and Spain, renting a car is a flexible and efficient choice, but remember to research cross-border fees and notify the rental company of your plans to avoid unexpected charges.
Solo Travel in Ethiopia: Preparation and Connection
Steph from Big World Small Pockets
Bio:
Stephanie Parker is the adventurous traveler behind Big World Small Pockets, a blog dedicated to budget travel, destination guides, and solo exploration. Known for her frugal approach to discovering the world, Stephanie provides practical tips and firsthand insights to help travelers make the most of their journeys without breaking the bank.
Her 2017 solo trip to Ethiopia stands out as a testament to her resourcefulness and adaptability. From leveraging airline discounts to connecting with fellow travelers in hostels, Stephanie showcases strategies for navigating less-traveled destinations with confidence and ease.
Through Big World Small Pockets, Stephanie inspires budget-conscious adventurers to embrace unique experiences, uncover hidden gems, and travel smarter while exploring the world.
Response:
"My greatest travel challenge was adventuring solo to Ethiopia in 2017, a destination where I didn’t know anyone who had been or what to expect.
To make the experience more manageable, I stayed at a hostel in Addis Ababa when I first arrived. This allowed me to meet other travelers who shared invaluable tips about exploring the best of the country.
I also ensured I booked my international flight with Ethiopian Airlines. This not only gave me peace of mind but also unlocked discounts on domestic flights within Ethiopia, which made getting around more affordable.
Additionally, I came prepared with plenty of USD cash to convert into local currency and brought an unlocked phone. With a local SIM card and data access, navigating the country became much easier. These small but important steps turned what could have been an overwhelming trip into an unforgettable adventure."
Key Takeaway:
Solo travel to less-explored destinations can seem daunting, but a mix of preparation, connectivity, and connecting with fellow travelers can transform the experience into one of personal growth and discovery.
A Wild Ride in Cuba: Lessons on Power and Patience
Namita from Radically Ever After
Bio:
Namita Kulkarni is a yoga teacher, writer, traveler, and artist from India who shares her adventures and insights through her popular blog, Radically Ever After. Since 2014, she has been blending her passion for solo travel, creative expression, and yoga to inspire her audience.
Recognized as one of the top 5 Solo Woman Travel Blogs in India and ranked among the top 50 Yoga blogs worldwide in 2017, Namita’s platform reflects her dedication to self-expression and meaningful connections. Her travels have taken her to South America, Thailand, Ladakh, and beyond, with highlights including leading a yoga retreat in the Valley of Flowers and exploring hidden gems like Triglav National Park in Slovenia and Himalayan villages.
Through her blog and social media presence, Namita shares her philosophy of living authentically, inspiring readers to embrace creativity, wellness, and the joy of exploration.
Response:
"One night in Cuba, I found myself in a wildly speeding police car after a conversation with a cop I met in the park. I’d shared my experience of falling victim to a scam a few days earlier, and he decided I needed to be taken to the station to file a formal complaint.
Upon arriving, things took a strange turn. The officer refused to let me out of the car. Desperate, I summoned every word of my broken Spanish to shout that I needed to use the bathroom. That finally worked, and I managed to get out.
Inside the station, the atmosphere was anything but welcoming. After some tense exchanges, I convinced them I’d return the next morning to complete the report. Instead, I headed back to my homestay in Old Havana. With my flight out of the country scheduled for the following day, I chose to leave without revisiting the station.
This experience taught me a valuable lesson: police in any country can abuse their power, and as a tourist, there’s often little you can do in such situations."
Key Takeaway:
Traveling abroad comes with its challenges, including navigating encounters with local authorities. Situations like these remind us to remain vigilant and prioritize our safety over formalities.
Spain is known for its vibrant cultural celebrations—be sure to check out our Spain Festivals 2025 guide to plan your trip around the best events.
A Baby’s Bottles and No Kettle: A Surprising Travel Hurdle
Rosana from Mama Málaga
Bio:
Rosana is the creator of MamaMalaga.com, a blog dedicated to family life, travel, and expat experiences in Málaga and the Costa del Sol. As an expat mother living in Spain, she shares practical advice and personal insights on:
Moving to Spain with a family
Navigating life in the Costa del Sol
Traveling with children across Spain and beyond
Through her blog, Rosana offers tips on local customs, schooling, and family-friendly activities, making it a go-to resource for expat families and travelers. Her writing, informed by real-life experiences—like navigating challenges during a family vacation near Barcelona—provides valuable perspectives to her readers.
MamaMalaga.com is a trusted guide for families looking to embrace life and travel in Spain to the fullest.
Response:
"One of my most challenging travel experiences happened during a family vacation to a small village near Barcelona. My son was less than a year old at the time and needed bottles prepared with boiled water every few hours.
When we arrived at the hotel, we discovered they didn’t have a kettle in the room—a surprising and stressful oversight given the importance of feeding a baby. The hotel management wasn’t able to help, and the village was too small to quickly find a kettle.
In the end, we improvised. Using mineral water and our bottle warmer, we heated the water to just above body temperature and managed to prepare his bottles. It wasn’t ideal, but it worked for the few days we were there. It was a surprising reminder that even the nicest hotels can lack basic amenities you might take for granted!"
Key Takeaway:
When traveling with young children, preparation is key—but flexibility and quick thinking can save the day when unexpected challenges arise.
The ‘Mañana’ Misunderstanding: A Lesson in Patience
Dave from Dave in Spain
Bio:
Dave and Sophie (Soph) are the British expats behind DaveInSpain.com, a blog offering honest, unfiltered insights into expat life and travel in Spain. With years of experience living in coastal areas, rural regions, and traditional villages, they share a genuine perspective on the challenges and joys of life abroad.
Dave’s diverse professional background—from working as a pastry chef to owning a service business, mystery shopping, and a decade in SEO and social media marketing—brings a unique touch to their content. Together, they created DaveInSpain.com to provide impartial reviews, authentic travel advice, and practical tips for fellow expats and travelers.
By steering clear of advertising-heavy content, Dave and Soph aim to offer an honest take on Spain, helping readers navigate the realities of moving, living, and exploring the country.
Response:
"One of my most amusing and challenging travel experiences happened when I was trying to sort out my padrón in Cuevas Del Campo. The town hall staff didn’t speak any English, so communication was already tricky.
For three days straight, I went in, only to be told that the person I needed to see wasn’t available. Each time, a colleague would assure me, ‘Mañana.’ Assuming they meant ‘come back tomorrow morning,’ I returned day after day, but no luck.
It wasn’t until a week later that I discovered ‘mañana’ can also mean ‘sometime in the future.’ As it turned out, the person I was waiting for had been on holiday the whole time! It was a funny, albeit slightly frustrating, lesson in the nuances of the Spanish language and culture."
Key Takeaway:
Cultural differences, especially in language, can lead to miscommunication. When navigating local systems abroad, patience and a sense of humor go a long way!
Lost in Translation: First-Time Adventures in Madrid
Gabriele P. from The Lithuanian Abroad
Bio:
Gabi, the creator of The Lithuanian Abroad, shares her passion for Spanish travel and expat life through detailed itineraries, travel tips, and practical resources for those exploring or moving to Spain. Her blog is a go-to guide for discovering Spain’s diverse destinations, offering insights into the culture, logistics, and hidden gems of the country.
From in-depth travel guides to relocation advice, The Lithuanian Abroad combines Gabi’s personal experiences and recommendations to inspire others to embrace the adventure of Spanish travel and expat living.
Response:
"The first time I visited Madrid with my mom, I barely spoke any Spanish. Communicating with locals in restaurants, museums, and other places was a constant challenge.
We relied heavily on Google Translate, fumbling through conversations but always trying to make the best of it. Despite the language barrier, the trip was full of laughter and funny moments that we still cherish. It reminded us that sometimes, the joy of travel is in embracing the unexpected and finding humor in the struggles."
Key Takeaway:
Language barriers can be intimidating, but a mix of technology, patience, and a positive attitude can turn challenges into unforgettable memories.
Last-Minute Hotel Cancellation in Mallorca: A Quick-Thinking Save
Michelle Trudie from Little Wanderblog
www.littlewanderblog.com
Bio: Michelle Trudie is the founder of Little Wanderblog, a luxury travel website dedicated to helping independent travelers discover stylish yet affordable experiences. She meticulously researches each destination, uncovering the best coffee spots, wine bars, and scenic locations to help travelers craft unforgettable, well-planned itineraries. Through her blog, she fosters a community of like-minded adventurers seeking stylish and authentic travel.
Response:
"One of my most recent travel challenges happened in Mallorca. I had planned my trip months in advance, visiting three different areas solo, with a final two-night beach stay booked for a relaxing end to my adventure.
Then, just days before I was set to check in, the hotel called to cancel—informing me that it would be closing. At the time, I was in the mountains of Sóller, it was late in the afternoon, and it was raining. I had to think fast.
I raced back to the small luxury boutique hotel I had just checked into and loved. With no reception on-site, I managed to catch the concierge just in time before she left for the evening. With the help of Google Translate, she contacted the owner, who found a way to accommodate me—even though their six suites were fully booked online!
In the end, it was a blessing in disguise. The following day was sunny and warm, giving me the chance to explore more of Mallorca’s villages and mountains. What started as a stressful situation turned into the best part of my trip!"
Key Takeaway:
Unexpected travel hiccups can turn into incredible experiences. Thinking quickly, staying flexible, and connecting with local hospitality can lead to even better adventures than originally planned.
A Near Breakdown in the Sierra Nevada: A Lesson in Preparedness
Lesley Stewart from Wander Somewhere
www.wandersomewhere.com
Bio:
Lesley Stewart is a professional travel blogger and Scotland itinerary specialist, best known for her blog Wander Somewhere. As a native Scotswoman, she has built a successful platform attracting over 130,000 monthly readers, offering expert guidance on slow road trips, hidden gems, and must-visit spots across Scotland.
Her blog provides in-depth travel guides covering where to stay, eat, and explore, helping travelers experience Scotland beyond the usual tourist trail. Lesley’s work has been featured in Condé Nast Traveler, and her Instagram, @lesleywanders, is a go-to resource for Scotland travel inspiration.
Through Wander Somewhere, she shares her deep love for Scotland, crafting thoughtful itineraries that showcase the country’s rugged landscapes, charming villages, and rich history.
Response:
"I live in Scotland but spend three months every winter traveling around Spain. I drive from the UK because I love the flexibility of having a car for exploring.
Last year, while driving on a remote road in the Sierra Nevada mountains, I hit a pothole, and soon after, my car started shaking violently. I pulled over and discovered that one of the wheel nuts had come loose—the entire wheel was at risk of falling off!
Even though I had breakdown insurance, I was in an isolated area, and it would take six hours for assistance to arrive. Worse still, I hadn’t packed much food or water for such a long wait. Just when I started feeling stranded, a passing Spanish farmer on a motorbike stopped to help. Using my very basic Spanish, I explained the problem, and he went to fetch some tools. Thankfully, he managed to fix the issue and got me safely back on the road.
It was an unnerving experience but also a reminder of the kindness of strangers and the importance of preparation when driving abroad."
Key Takeaway:
When driving in remote areas, always be prepared for unexpected challenges. Carry essentials like food, water, and emergency supplies alongside legally required items like warning triangles. And even a little knowledge of the local language can go a long way in a tough situation.
Lost in Translation: An Unexpected Climbing Adventure
Cristina Reina from My Little World of Travelling
www.mylittleworldoftravelling.com
Bio:
Cristina Reina is the founder of My Little World of Travelling, a blog dedicated to uncovering the beauty of Málaga and Southern Spain. As a Málaga native, she offers local insights, detailed destination guides, and hidden gems to help travelers experience the region authentically.
A travel writer and content creator, Cristina specializes in crafting in-depth guides that go beyond the typical tourist spots, providing a true taste of Andalusian culture. Through her blog and active presence on social media, she shares exclusive local knowledge, inspiring visitors to explore Málaga and the Costa del Sol with a deeper understanding.
Follow her journey and discover Southern Spain through her blog, My Little World of Travelling, or connect with her on social media for expert travel tips and resources.
Response:
"I once joined a group trip, thinking I knew exactly what to expect after reading the description. Since I’m fluent in the language, I skimmed through the itinerary without paying close attention to every word.
I packed my bag, assuming one of the activities was a short walk in the countryside. Then, just 20 minutes before my train was about to leave, the organizer called to check if I was on my way—and to confirm I had everything I needed for the climbing experience.
When I heard the word ‘climbing,’ I panicked. I had never done it before and certainly hadn’t packed for it. All I had with me were brand-new clothes, completely unsuitable for an outdoor adventure. With just minutes to spare, I sprinted to a nearby shop and grabbed a pair of leggings.
On the day of the climb, I was incredibly nervous, but once the instructor explained everything and strapped us into harnesses, I started to feel more comfortable. To my surprise, I loved the experience! What started as an intimidating challenge turned into something I’d love to do again.
This experience taught me two things: first, believe in yourself and push past your fears—you might surprise yourself! And second, when in doubt, always ask questions instead of making assumptions!"
Key Takeaway:
Sometimes, the best travel experiences come from unexpected challenges. Whether it’s misinterpreting an itinerary or stepping outside your comfort zone, embracing the unknown can lead to incredible adventures.
Overcoming Challenges, One Journey at a Time
Lucia from Viva La Vita
https://www.thevivalavita.com/
Bio:
Lucia is the founder, writer, and photographer behind Viva La Vita, a travel blog dedicated to uncovering the authentic beauty of Southern Spain. Originally from Slovakia, she has lived in multiple countries, including London and Cyprus, before settling in Fuengirola on the Costa del Sol in 2020. Since launching her blog in 2015, she has inspired travelers—particularly women aged 25 to 45—to explore Spain beyond the typical tourist trail.
With a background in marketing and a passion for photography, Lucia crafts engaging, well-researched content that highlights hidden gems, local culture, and sustainable travel practices. Through Viva La Vita, she continues to share her love for travel, helping visitors connect with the heart of Southern Spain through personal insights and stunning visuals.
Response:
"I planned a trip to Gibraltar with my husband and two young kids, excited to explore the famous Nature Reserve. What I didn’t realize was how difficult it would be to navigate the steep, winding roads with a baby pram.
Dragging a stroller up and down rocky paths in the heat wasn’t my idea of fun, so I quickly searched for alternatives. That’s when I found a local tour company offering mini-van trips through the reserve. It was a game-changer.
Instead of exhausting ourselves climbing endless hills, we sat comfortably in an air-conditioned van while watching other travelers struggle in the heat. Our guide shared fascinating local insights, and best of all, he took us to the perfect spot to watch the famous Gibraltar monkeys running freely around the reserve.
Since that trip, I always recommend this option to friends visiting Gibraltar. It’s a huge time-saver and makes the experience so much more enjoyable!"
Key Takeaway:
When traveling, don’t be afraid to rethink your plans if things seem impractical. A little research and flexibility can turn a tough situation into a seamless, stress-free adventure.
Overcoming Challenges, One Journey at a Time
Travel isn’t always smooth sailing—it’s filled with unexpected detours, cultural differences, and moments that test our patience and creativity. As these stories from seasoned travel writers show, even the most challenging experiences can lead to laughter, growth, and unforgettable memories.
Whether you’re navigating a new language, stranded in a remote location, or improvising solutions on the fly, the beauty of travel lies in its unpredictability. Challenges aren’t just obstacles; they’re opportunities to connect, adapt, and discover new perspectives.
Ready to take on your next adventure? Don’t let the fear of challenges hold you back—embrace them as part of the journey. And when the unexpected happens, remember: there’s always a way forward, often with a sense of humor and a great story to share afterward.
Have you faced a travel challenge that left a lasting impression? Share your story in the comments or on social media—we’d love to hear how you turned a tough moment into an unforgettable experience!
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