Best Worst Travel Experiences of 2019

2020 is going to be a year of flat tires, wrong turns, and getting out over our ski tips. At least, if we at Lost Travel have anything say about it. Let’s not get ahead of ourselves just yet though. We asked the Lost community to look through the rear view mirror.

“Tell us a travel story,” we said, “that isn’t about sunshine and rainbows.”

“Sure” they responded, with the halfhearted enthusiasm that we’ve grown to love about them.

Without further adieu, we present you with the Best Worst Travel Experiences of the year gone by.

1) First / Worst Cruise

My fiancé and I booked a 10-day cruise to celebrate our engagement. She’d been skeptical about cruising after hearing nightmare stories about illnesses but I convinced her that’s a rare occurrence.

400 cases of the Norovirus happened that trip.

No more cruises for us. – Jared

2) Best Motorbike Jump Ever

During one of the last days of the Monkey Run in Romania we were riding a rocky back road of the southern Carpathian Mountains towards the Transalpina Highway. We had made pretty good progress this day and our gang was in good spirits so I decided to have a little fun and jump my monkey bike off a large rock in the road. But I slightly miscalculated the effect of the earth’s rotational spin and ending up eating shit. A bunch of parts on my bike were trashed and I tore a hole in my leg. The best part was the reaction of the person behind me who saw the whole thing. “So what were you trying to do?” – Carol | And yep, it was caught on film.

3) Who needs Ferry Schedules?

After just a couple hours in Venice, you get tired of tourists and crowds. So, our second day in the city, we took a ferry boat out to an island an hour away from the main island, to explore lesser-frequented spots and to get some breathing room. We had a lovely evening drinking aperol spritzes on this tiny Venetian island, watching the setting sun turn everything aperol-colored. But when we strolled to the dock to catch the ferry ride back to Venice to find some dinner, we were greeted with pandemonium. The off-season had rendered the ferry schedule signs completely inaccurate, so as boat after boat never arrived, the crowd on the dock grew frantic. Would we be trapped on a tiny island with only one bar and an ancient church all night? Taking advantage of the crowds gathering around the schedule signposting, I sidled right to the edge of the pier to position us as the first to get on any boat that arrived. I’ve seen Titanic, I know how this shit goes down. 

Finally, a boat arrived, and the crew informed us we’d have to go with them to another island, where we’d get off and catch the ferry back to Venice. That didn’t seem correct to me, but we got on, along with half the crowd. The other half stayed behind, not wanting to risk moving further away from Venice. At the next island, the crowds were even bigger and more confused, and every crew member had a different story for which line would get you on a boat to Venice. Rather than following the chaotic masses, we stuck with a group of 20-something girls, who charmed a ferry operator to finally let us onto the correct boat. A lot of people stayed behind in the confusion, no longer trusting anything any Venetian boat operator had to say to them. For all I know they may still be sitting in line on that dark, empty island. – Danny

4) You Shall Not Pass

For those not familiar with the geography of Sri Lanka, it’s basically a little tear drop shape with a big hilly bit in the middle, like a fried egg. We spent the better part of a day chugging our little 6hp rickshaws up the 1400 meter craggy yolk only to reach the summit and find the only road down the other side was closed. Just three guys in orange vests smoking cigarettes separated us from not spending the rest of the day driving back down to where we started that morning. Being the Midwestern nice people that we are, we just said ‘Ope!’, smiled and turned around to start the 6 hour trek back. We later heard that a team of Europeans badgered the workers into letting them through.  – Walker

5) Favorite Flight of 2019

On our approach to Cluj-Napoca, the sky got very dark and the small plane started bucking violently. After what felt like 5 entire minutes inside a Shake Weight and getting close enough to see the lines on the runway, the pilot pulled back up and banked hard left into calmer air. We spent 10 minutes in quiet unease until the pilot came over the speaker and said… “Halo. I was going to land in Cluj, but I didn’t want to.” Then… silence.

45 minutes later we landed in a small Romanian town with no instruction and no baggage but we were given meal vouchers, which we exchanged for beer. We sat on the tile airport floor, drinking and debating our next move. Around 11pm a bus to Cluj arrived but we weren’t pushy enough to get on. Around 12:30am another bus arrived, which we rode until 2:30am at which point it started filling with thick smoke and broke down. A small van arrived around 3:15am (we still don’t know who called it). We got in, said “Klooshz” to the driver, and took a cat nap. 1 hour later we were dropped off in the center of Cluj-Napoca, bleary-eyed and with no clothes to change into. – Jake

6) Worst Gas Station

I was working on a fishing boat as a mate for a week long trip. We departed Miami toward the Bahamas and had a beautiful crossing of the Gulf Stream, seeing pilot whales and birds. The fishing was slow so after a few days we began packing up and headed to the local watering hole. This turned into a tour of the island including the farm, future solar field, power plant and the whole time one of the employees is telling us how much diesel they have. “How much?” we ask. “Ten 10,000’s,” he replies. A bit confused, we just assumed he wasn’t too great at math and we carried on. Later, he shows us the fuel tanks and there are, in fact, ten 10,000 gallon tanks (now it all makes sense). We take note because our plan the following day was to fuel up and head back early to bypass oncoming weather.

We wake up and visit the ten 10,000’s and… they’re out of fuel?!? Bewildered, with the storm approaching, and with no where to stay, we pull into Bimini. We party all night and all 13 of us end up sleeping on the boat, me on the kitchen floor. We woke up to wicked hangovers and a broken golf cart (vaguely remember driving this to a bar) which we returned to a rental agency before they opened. The seas were rough and we were all a little worse for wear which led to some vomit as we cooked Jimmy Dean sausages on the MTU diesels. The Coast Guard stopped us as we crossed back into US waters and we surely must have looked like a trainwreck (or rather, shipwreck). We never figured out the deal with the fuel. – Blake

7) First Flat Tire on a Motorbike

Riding a 50 cc motorbike through the Moroccan countryside sounds like a dream….until the back tire blows out while zooming at a staggering 20 mph through the desert. After attempting to slow myself down, I decided to gently squeeze the handbrake, activating crash-landing mode. I flew off the bike and rolled out nicely with nothing but a small rip in my jacket, exclaiming “I think I got that on GoPro”. – Ben | Spoiler, he definitely did get it on GoPro

8) Worst Cab Ride

We took a 6 hour “Cab ride” in a non air conditioned cargo van to Bucharest while being extremely hungover. It was so hot the driver allowed us to drive down the highway with the entire side door wide open.

The forced smiles in this photo do not give justice to the misery we were in. It had been days since we showered. Also, it should be noted that there’s somebody sitting on the floor (adjacent to the open door) because there isn’t enough room on the seats. – Farshid

9) Drenched Drifty

It was the last night of the Driftless 250, my brother and I were camping out at Blue Mound State Park. Thus far into the trip, we had been extremely lucky with weather, however, on this final night mother nature decided to make up for lost time. Luckily for my brother, he packed a rain fly for his hammock; unluckily for me, I brought one tarp that failed to cover the entirety of my hammock. Making due with what I had, I draped the tarp over my hammock using some rope. As the night continued, so did the wind and rain, and my hammock, sleeping bag, and self got increasingly more drenched. But to my rescue comes my big brother, with his abundance of Carabiners and rope, to save the day! While huddled in my wet hammock, he secured my tarp on the bottom and corners of he hammock so that less rain could spill through. Looking back, maybe this should be a worst travel experience for him since he was getting soaked trying to fix a makeshift rainfly, but I’ll still take this one. – Kiley

10) Worst Mileage Run

Lastly, we can’t help but share this beautiful travel fail.

It started as an innocent mileage run and it reads like a movie script: twitter.com/andrewkimmel/status/1212156209320513536

Fortunately for all of us, adventure is not the antidote to wanderlust, it is the seed of it. We can’t wait to get out there in 2020. Join us and we’ll see what sort of nonsense we can get into.

See what’s on the docket for 2020 at lost.travel/calendar.

Want more? Check out our 2018 list of Best Worst Travel Experiences.