All Time Best & Worst Travel Moments

Reflecting on all my best and worst travel moments from the last few years.

2019 and the entire last decade are both coming to an end.

I have to say 2019 was the wildest year of my life. I went through some crazy things this year, positive and negative.

Reminiscing about these insane moments from 2019 has me comparing them to noteworthy moments from the last few years as well, so I’ve decided to compile these memories into a list!

I have been traveling pretty consistently for the last four years now.

I’ve traveled alone, with friends, with boyfriends and with random people I just met.

I’ve lived in massive cities, lazy beach towns and remote jungle villages.

I’ve made so many amazing memories but I’ve also faced a lot of obstacles.

Though I always try to focus on the bright side, I want to emphasize that traveling isn’t always fun and life isn’t always easy.

cape tribulation australia
Cape Tribulation, Australia

So here are my best and worst moments that I’ve had while traveling in recent years (Listed in no particular order).

Best Travel Moments

Climbing the colorful peaks of Rainbow Mountain, Peru

Spending an entire day biking from waterfall to waterfall with a bunch of people I just met in Baños, Ecuador

Befriending six adorable puppies in rural South Africa, scrubbing them with flea shampoo and cuddling with them every day once their fleas were gone

Drinking wine and eating sushi in a secret underground bar in Prague with my Dad and MJ

Improvising Halloween costumes in the Costa Rican jungle with all the coolest people ever

costa rica travel
Halloween 2017 with some legends in the Costa Rican jungle

Partying at Bermuda‘s annual island-wide party known as “Beachfest” with Ayana, Jazmyn, and her family and friends

Climbing the Sticky Waterfall in northern Thailand, where the rocks are covered in rough mineral deposits so you can literally climb up the waterfall like spiderman

Headbanging at a heavy metal nightclub in Bulgaria

Taking a day trip from Dubrovnik, Croatia to Lokrum Island and spending the whole day swimming in cold turquoise waters all by myself

Hiking up to Castelo Dos Mouros and Pena Palance in Sintra, Portugal

pena palace sintra portugal
The gorgeous Pena Palace in Sintra, Portugal

Appearing on the local news in Guatemala for paddleboarding down the flooded city streets in the rain

Watching a breathtaking Flamenco Show in Madrid

Living and working in the oldest rainforest on the planet in Cape Tribulation, Australia and becoming super close with all my hilarious coworkers

Going on two safaris in South Africa and seeing lions, rhinos, giraffes, elephants, zebras, buffalo and other incredible animals in real life

Snorkeling in the Great Barrier Reef, Australia

great barrier reef australia
Snorkeling with a sea turtle in the Great Barrier Reef

Partying with my best friends in Cairns, Australia and winning all the dance contests

Swimming in Iceland’s geothermal Blue Lagoon

Walking barefoot on the soft, warm sand dunes of the Sahara Desert

Having a decent conversation using only hand gestures with a super sweet old bearded man in Croatia on a random park bench (He then offered me vodka from his shirt pocket, in a totally non-threatening way)

Road-tripping around Scotland with my Mother

Spending two weeks with a local family in Ecuador and learning more Spanish than I ever did in five years of school

ecuador volunteer
Exploring Cotopaxi National Park in Ecuador with my local host family

Camping next to Volcán Fuego in Guatemala and watching red hot lava erupt all evening

Sampling all the crazy cheeses at Amsterdam’s Cheese Museum

Spending 10 days in Kuaui, Hawaii with my mom, sister, aunt and grandmother, snorkeling, hiking, kayaking, swimming, zip-lining and tasting exotic fruits and chocolates

Skiing in the Italian Alps

Skiing in the Swiss Alps

skiing swiss alps
Skiing in Grindelwald, Switzerland while working as a tour guide for Smart Trip

Experiencing my first Australian Christmas which consisted of working hard all day as a bartender at Steamers, eating all the delicious leftover seafood and cheese boards, then having a beach party with my awesome coworkers

Attending a musical, colorful and sweaty local church ceremony in rural South Africa

Taking a Thai cooking class in Chiang Mai with Justine and eating our body weight in pad thai, spring rolls, green curry, cashew stir fry, papaya salad and mango sticky rice

Watching my animal-loving Mom and Sister feed kangaroos for the first time

kangaroo australia
My Mother, unable to contain her excitement after feeding a kangaroo

Learning how to surf and how to salsa dance in Costa Rica

Signing my first lease ever, on an apartment in Wollongong, Australia with Matt

Trekking for 10 hours in the Atlas Mountains to a rural village and massive waterfall

Living in a tiny apartment in Rome with six people and having a crazy five months together while working as tour guides and tour promoters for Smart Trip

rome friends travel
My insane yet lovable roommates in Rome

Hiking Lion’s Head Mountain in Cape Town at sunrise on my 24th birthday

Attending a dinner party with a local Polish family outside Warsaw

Visiting the Cliffs of Moher and eating the best doughnut of my life in Galway with Melissa

Spending a week living off the grid, learning about permaculture and eating vegan food in the forests of South Africa

south african forest
Nightly campfires at Pachamama Forest Retreat near Knysna, South Africa

Attending the Festival of Lights in Quito, Ecuador

Hiking Mount Snowdon, the highest mountain in Wales

Visiting the charming little villages of Transylvania, Romania

Returning to Soave, the small town in northern Italy where I used to live as a child and seeing all the locals who were like family to me (Also sharing a bottle of wine with one of our dear family friends, Pier Paolo, who has been trying to get me to like wine since I was about 8 years old)

italy wine
Celebrating my new love for wine with Pier Paolo in Soave, Italy

Spending New Years Eve 2015 in Madrid with my cousin and eating twelve grapes for each ring of the clock like the Spaniards do

Taking my first solo trip ever, to Copenhagen, Denmark

Biking, rock-climbing, hiking and exploring in the Czech Republic with my two favorite legends, Michael and Shara

Road-tripping down the east coast of Australia with Matt after finishing three months of farm work

aussie roadtrip
Matt at the beginning of our road trip in our friend’s van

Serving as an unofficial London tour guide whenever I revisit my favorite city with various friends

Touring ancient temples in Cambodia

Bathing naked with Hungarian women at a local bathhouse in Budapest

Sightseeing in Chefchaouen, Morocco and finding a box full of precious kittens in the blue streets

kitten chefchaouen morocco
The most beautiful photo to come out of our Morocco trip, taken by my boyfriend Matt

Paddleboarding through a thunderstorm in Lake Atitlán, Guatemala

Taking a solo trip to Spain during my junior year of college to practice for my upcoming Spanish exam

Practicing my Spanish by telling a waitress in Spain that I needed to get to the airport; She literally left her cafe to personally drive me to the airport for free

Kayaking between limestone cliffs in Thailand

kayaking thailand
Justine and I on our kayaking tour in Ang Thong Marine Park, Thailand

Eating baguettes next to the Eiffel Tower with my cousin, Elaina

Flying Japan Airlines on my 22nd birthday and the staff sang Happy Birthday to me and gave me a handwritten card and a toy airplane

Hiking in Montenegro’s breathtaking Bay of Kotor

Visiting the ancient Rila Monastery in Bulgaria and hiking through the snow to the tiny frozen cave where St. Ivan of Rila actually lived as a hermit for years before founding the famous monastery

Celebrating my first Thanksgiving abroad in my London apartment with amazing people

london thanksgiving
An international Thanksgiving in our London flat

Swimming in the gorgeous natural pools of Semuc Champey in Guatemala with absolutely no other tourists around

Tasting delicious Swedish cinnamon rolls in Stockholm

Wine tastings in South Africa, Hungary, Australia, Portugal, Italy…..pretty much every wine tasting I’ve ever done makes the list

Going to a Chelsea game with my dad in London

chelsea game london
Our favorite team in the BPL, notice how we don’t look alike at all

 

Worst Travel Moments

The guy in the bunk next to me in the Guatemalan jungle found a massive furry tarantula in his bed, and we watched in horror as the local guys tried to get it out of the dorm with a rake

First beach day in Thailand and Justine and I both got so sunburned we could barely move

Taking a taxi to a random suburb in Ecuador at 11pm for my first ever work exchange, only to find the family wasn’t home and panicking while trying to figure out where to go

Missing a flight from London to Germany with my Dad (We just took a later flight, but that feeling of knowing you missed a flight makes you feel like a failure)

Getting stranded at the bus station in Puno, Peru because all the overnight buses back to Cusco went on strike

puno peru bus station
Isabela and I excited to FINALLY get bus tickets back to Cusco after waiting at the Puno bus station for hours

Matt and I getting harassed in an alleyway by a local guy in Fez, Morocco who wanted us to pay more than the money we had in our wallets for a tour that we didn’t ask for

Getting bit by a dog in South Africa and having to get four rabies shots plus two extremely painful immuno-globulin shots

Every time I book a super early flight because it’s cheap and immediately dread waking up in the middle of the night for the journey

Apple picking in Australia. Hard work, little money, read my full article here: Life As A Fruit Picker In Australia

Having to leave my first farm work job in the Daintree Rainforest because the business went up in flames

australian backpackers farm work
The whole crew of backpackers on one of our last nights in the Daintree Rainforest

Seeing little monkeys on chains in the main square of Marrakech, Morocco, and witnessing other forms of animal exploitation around the country

Walking through the Australian jungle in the dark and my friend stepped on a giant python (Nothing bad happened it just scared the living daylights out of us)

Testing positive for Lyme disease after a tick bite in the UK

Trying to get treatment for said Lyme disease while living in Australia, where Lyme disease is very rare and every doctor I saw had no idea what to do. The first doctor I saw just Googled “Lyme disease” right in front of me. The second doctor I saw who gave me the blood test absolutely panicked when he saw the results. Since he couldn’t reach me because I was at work he ended up calling the real estate company of the apartment I was living in. Then the real estate company called my roommates, scaring them into thinking I was getting in trouble for living there without my name on the lease. So EVERYONE was panicking, when all I had to do was get antibiotics and I ended up fine.

Traveling from the hot, humid Costa Rican jungle directly to the dry, freezing cold New England winter and developing a horrible flu for weeks

new england dog house
Though I was suffering from a raging flu, being home in the winter is always pretty magical

Spending a night in dusty, abandoned cabins in the Daintree Rainforest at an off-grid bat rehabilitation center because we had to leave our jobs. The bathrooms were up in treehouses, had no doors and had massive spiders hanging in front of the toilets

Canceling my five-day Salkantay Trek to Machu Picchu in Peru, which I was SO excited for, because I was sick with the flu

Visiting Latvia in the middle of winter, during a snowstorm, with only a few hours of daylight, and I had the flu (Yes, I get the flu a lot and sometimes it really ruins a trip)

Dealing with long-distance relationships WAY too often

Stepping on a sea urchin while snorkeling in Thailand and having the local guide tell me he can’t remove the spines so I just have to wait for them to dissolve (To speed up the dissolving process he then pressed super hard on my foot to try and push the spines in more; I had stabbing pains in that foot for months)

Spending two nights in a row sleeping in airports during a long layover and feeling insanely dehydrated and exhausted

Matt getting crazy bed bugs in Morocco, this didn’t happen to me but I felt SO BAD

Sprinting down the streets of London with my huge backpack at 3am so I didn’t miss the last bus to the airport for an early flight (I made the bus, but that was an insanely stressful five minutes that I will never forget)

My beloved iPod classic that I’ve had since 2006 finally dying last year; I feel so empty traveling without it

Having my second year working holiday visa for Australia denied because of a paperwork issue that wasn’t even my fault. That was a crushing blow, but Matt and I will find a way to turn the situation around 🙂

australia beach new south wales
Hopefully I’ll be back in Australia with this guy soon!!

So there have been some bad moments while traveling.

But the good moments outweigh the bad by SO MUCH.

Starting to travel was the best decision I ever made. It’s brought beautiful people into my life and taught me lots of life skills that I never could have learned from staying at home.

Luckily, none of these negative travel memories have been that serious, and most of them make pretty funny stories now.

There are good and bad people in every country. If you have a positive attitude and an open mind, you’ll find that most people are kind-hearted and compassionate deep down.

So I honestly hope that this blog post inspires people to travel more! Even if it’s just traveling to a different part of your own country, get out there and do something.

Talk to different people, learn new skills, eat weird foods, create new art, push yourself out of your comfort zone and you’ll be amazed at how much you can grow.

If I’ve convinced you, check out my ultimate guide for traveling on a budget: How To Afford Traveling The World In Your 20’s and my Ultimate Guide for Finding Cheap Flights.

THANK YOU FOR READING

ALL TIME BEST & WORST TRAVEL MOMENTS

2 thoughts on “All Time Best & Worst Travel Moments

  1. Alex Marsh

    Hi! I really like your blog. I’d like to get more advice from you on how to start traveling if you’re willing, especially how to work while traveling?? I’m wanting to start in the next 1-2 years. Thanks

    Like

    1. Gabby Boucher

      Thanks so much! 🙂 All you need to start traveling is a bit of money saved and a willingness to just book a plane ticket! (And a passport if you don’t already have one).

      As for working while traveling, you can very easily do a work exchange, which is unpaid but you get free accommodation in exchange for your hours. You can also apply for seasonal jobs at resorts, ski lodges/surf camps, or tour companies.

      I wrote a very detailed article about all these topics if you want some more info: https://gabbyboucher.com/2018/09/28/how-to-afford-travelling-the-world-in-your-20s/

      Like

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