Happy Halloween!
Forget haunted houses. The scariest things that have ever happened to me were on the road!! I've been to more than 80 countries. That's a lot of trips. And a lot of chances for things to go wrong!
I've made almost every mistake you can make in travel, and most of these mistakes are why I plan the way I do now.
So in honor of the spookiest weekend of the year, here are my real-life travel horror stories…
The tea fields of Nuwara Eliya
Sri Lanka, booked all by myself
I booked every hotel in Sri Lanka myself. A country I knew NOTHING about.
In Nuwara Eliya, the staff stared at me like I was a creature from outer space. (They were fascinated by my blue eyes, they said. But it was creepy staring.) In Kandy, I didn't feel safe in my hotel. In Galle, my driver and the hotel proprietor got into a screaming match in front of me, while I stood there alone with my bags. The driver had been recommended to me by friends who had been to Sri Lanka exactly once, a few years prior. He was…not a great guy. Midway through the trip, he admitted he’d been in jail in Dubai. Because I had booked him over WhatsApp and had already paid him, I felt stuck with him for a week. (Now the economist in me would say…never make any decision based on a sunk cost.)
I could have used a travel advisor for that trip. I would have been so much happier on a professionally organized trip with support just a phone call or WhatsApp away.
This is exactly what I do for clients now. When you're going somewhere new, I book hotels I know and trust, and I line up vetted private drivers who show up on time and don't pick fights with the front desk. If there's a destination on your list that feels a little intimidating, let's talk it through.
Serbia has yet to meet a cigarette smoker it doesn’t like, btw.
Belgrade Serbia, in an Airbnb
Traveling solo in Belgrade, Serbia, I booked an Airbnb. The front door of the apartment building was unlocked. The stairwells were dark and people came and went at all hours of the day and night because of some sort of office on the 2nd floor. There was no safe in the apartment, and cleaning people were in and out of my apartment at odd times of the day.
Never again!
I would have been so much more comfortable in a hotel. Honestly, I've learned I enjoy interacting with hotel staff. Someone at the desk who knows your name. Someone to ask for restaurant recommendations. That's worth a lot when you're on your own. Now as a Virtuoso travel advisor, I only book vetted apartments where I know someone will be there for my clients if something goes wrong.
As I joked to my dad “Yes dad, they have taxis in Syria.”
Damascus Syria, with food poisoning
I got food poisoning in Syria at the very end of my trip. I was supposed to stay a few more days on my own before flying home to London, but I was miserable. I was staying in a lower 4 star hotel and it was fine but I was in a strange city and feeling like crap. (Shout out to the amazing Syrian pharmacist though who helped me out though. I love pharmacists in other countries.)
Weary, I called the Four Seasons Damascus. Four Seasons to the rescue! Yes I was still sick, but I felt 1000% better in a 5 star hotel used to Western tourists. (Sadly the Four Seasons Damascus is no longer — the building still exists, but it’s run by the UN now, I hear.)
Lesson learned: Don't suffer in a hotel that’s just okay. When you're sick and far from home, a great hotel with great staff is everything.
As a Four Seasons Preferred Partner, I can add perks to your Four Seasons stays, typically daily breakfast for two, a property credit, and an upgrade, early check-in and late check-out when available. Nice to have when you're well. A lifesaver when you're not.
Kuwait City has some cool architecture.
Stuck in Kuwait for 24 more hours
Back when I was working in the Middle East, my flight from Kuwait City to Washington, DC was cancelled. I was stuck in Kuwait for another 24 hours.
Luckily, because I’d been at the hotel for so long, I'd built a good rapport with the front desk staff. I made one quick phone call, they instantly knew who I was, and the hotel picked me up in no time whatsoever. The next day, I asked them to find me a local travel agency to show me the parts of Kuwait City I hadn't seen yet. A cancelled flight turned into a fun bonus day!
That's the whole idea behind how I plan trips. Relationships matter. When something goes sideways, my clients have someone in their corner: VIP arrival and departure service at the airport, a vetted driver waiting, and a hotel that already knows they're coming. And private touring is my specialty, so a surprise extra day can be more of a positive than a negative. Book a free consultation and I'll build that safety net into your next trip.
Kuwait is a really fascinating place to visit, by the way. I really enjoyed my time there. I was a teenager during Desert Storm — it was amazing to me how 20+ years later, Kuwaitis were thanking ME for everything America did to liberate Kuwait.
A 4 a.m. hospital run in Playa del Carmen
This summer, I ended up at a hospital in Playa del Carmen at 4 a.m. with a friend who didn't have travel insurance. Stressful!! The adventure cost her $1000…and she was lucky that her issue wasn’t more serious!
Buy travel insurance. Please. I help every client choose a plan that fits the trip, so you're covered before you need it.
Mandalay, Myanmar. If you are into historical fiction, I can recommend The Glass Palace by Amitav Ghosh
The gas station in Mandalay
My ride from my hotel to the airport in Mandalay, Myanmar, is still one of the strangest rides of my life.
The driver was sketchy from the start. In a bad mood. Very distracted. He didn't speak much English. Then halfway into our ride, he pulled into a gas station, got out of the car, and left me sitting there. With ALL my belongings locked in the trunk.
I couldn’t help but wonder…”Am I about to get robbed? Are they taking my luggage??”
We sat at that gas station for a really long time. We did not get gas. He had a very long conversation with someone. There seemed to be some disagreement. And they kept looking at me.
To this day, I have no idea why we stopped or what was going on. Maybe they decided I wasn't worth kidnapping.
This is why I only send clients with vetted drivers. You should never be sitting in a car wondering whether your driver is about to sell you out.
MSC, even in Yacht Club
I sailed with MSC earlier this year. My cousin wanted to try it. Not my scene, even in Yacht Club. The ship was so dark! Most people on the ship seemed to be there to drink.
I longed for the light and airy cabins and decks on Silversea.
This is why I always say there's a cruise out there for everyone. The trick is finding the right one for YOU. I've sailed a lot of ships, and matching people to the right cruise line is one of the most useful things I do. Not sure which ship is yours? Let’s figure it out together.
Always learning…
Every one of these stories has taught me something. Most of these situations are why I plan trips the way I do: hotels I trust, drivers I've vetted, a plan B already in place, and someone to call when things go wrong.
You don't have to learn these lessons the hard way. I already did. Schedule a free consultation and let's plan a trip with no scary surprises.
Happy Halloween!
Krista
About Krista
I’m a Virtuoso travel advisor based in Palm Beach, Florida. I attended the University of Notre Dame for undergrad and I have my MBA from the University of Chicago. Before building my travel business, I spent 20 years in the investment management industry and over a decade living and working in London, England. I’ve personally traveled to 80+ countries and now design thoughtful, highly customized trips for travelers who value expertise, access, and a seamless experience.
I offer a complimentary 30-minute consultation for travelers considering a custom itinerary or luxury cruise. Book a complimentary vacation consultation here.
For travel inspiration and real-time updates, you can follow along on Instagram or connect with me on Facebook. I also share a curated list of travel products I genuinely use and recommend in my Amazon store.
What I Offer…
Custom itinerary design for complex, multi-stop trips
VIP hotel benefits through Virtuoso and preferred partner programs (including complimentary breakfast, hotel credits, and priority for upgrades where available)
Luxury ocean, river, and expedition cruises with added onboard credits
Vetted villa rentals with concierge services worldwide
Private guides, small-group touring, and unique local experiences
Private aviation and yacht charters through trusted partners
Airport transfers, VIP arrival and departure services, and full ground logistics
Travel protection and support when plans change
I work best with travelers who want expert planning, trusted partnerships, and someone in their corner from start to finish. That’s what I am best at! Ready to talk travel? Book a complimentary vacation consultation here.
