Flirting With Disaster

My number one travel tip is a difficult one for me to suggest to my clients. The travel motto my husband’s and I have is, “The best trips are the trips where something goes wrong.”

We’ve travelled a lot together, we’ve seen beautiful cities, beautiful beaches, met lovely people … but if I’m being honest, there’s something just so vanilla about those trips. Don’t get me wrong, I do not wish disaster upon myself or anyone, but it’s when things go wrong that the opportunity for truly great memories and excellent stories are born.

I also think it’s an excellent travel philosophy for anyone who travels frequently, you need to roll with the punches. When you come back from a trip it’s much better to come back ‘glass half full’ with stories about your travel adventures, vs ‘glass half empty’ with a bitter taste in your mouth and a laundry list of negativity to post on TripAdvisor.

In 2015, Dave and I decided to go to Europe, starting in Greece, with a sailing trip through the islands, followed by a weekend in Munich for Oktoberfest, and closing it off with a stop in Iceland. When we reflect back on it, Iceland and Germany were lovely, but it was Greece that we will remember forever… I’ll give you a little taste, we racked up about a €50,000 insurance claim.

It all started pleasantly enough, we arrived into Mykonos in the morning, taxied to our little hotel, and then enjoyed 3 lovely days of exploring beaches, sea kayaking, and perusing markets.

At the start of day 4 we made our way to a local restaurant to meet with our Greek Island Sailing tour group (no need to mention the tour company name, they were great, but the chaos that ensued was pure acts of god and misinterpretation on our part).

The group comprised of a couple Americans, a few Irish gals, a lone Australian, and us – the Canadians. We spent the day getting a tour of the boat, a tour of Mykonos, and closed it off with a movie under the stars.


The next day we were set to sail to the next island. It was a windy day, but our Skipper had endured far far worse and was ready to hit the open seas. We were each assigned positions… some were in charge of sails, some would relay messages from the Skipper to the front of the ship, and we were relegated to lift the anchor.

The boat engine started up (to get us out of the marina) and we were OFF!… for about 20 feet. Suddenly the boat was overcome by the wind, unaided by the engine which had given out, and we careened across the marina toward a giant concrete pier and several large, expensive ships. Our crafty Skipper hailed an incoming zodiac boat for help, and they were quick enough to guide us back to our original pier, much to the chagrin of our new neighbouring ship which got banged around a bit. “Not a worry”, our Skipper told the ship’s owner, “The insurance will be sorted out by the tour company.”

We all stood at our stations, awaiting news as our Skipper inspected the damage below. After a few minutes he reappeared, pointed at us, and said, “You two… come down here and check this out.” Not being marine experts, surely we weren’t being called down for our professional opinion. We approached our cabin below deck, and our grinning Skipper held out a ragged strap of fabric bearing a MEC logo, “Does this look familiar to either of you?”… It was a strap from Dave’s 60 litre metal framed backpack. He then directed us to look in a little cubby at the engine. It was dark, so we used his flashlight to peer in, and there was the smoking ship engine completely torn apart by the shrapnel, fabric, and contents of Dave’s backpack. The walls were also splattered with a combination of engine oil and Tim Horton’s French Vanilla Coffee powder… a gift we had brought for my friend in Germany. It looked like a horror show, but it smelled like home.


Our Skipper, not without a heavy dose of irony and sarcasm, asked how on earth we got the idea to put a backpack on the engine. Sheepishly we explained that when he had given the ship tour, he had instructed us to store our clothes in the closet and store our bag in the cubby. He nodded silently, and then indicated another cubby and said, “Did it not cross your minds to store your bags in the cubby that did not contain an engine??”

Truly, that was the worst of it from him… he explained that there were other Skippers at the tour company that would have flown off the handle and berated us, but when it came down to it that’s what insurance was there for, and it wasn’t going to cost us or him anything. So we did not leave Mykonos that day, and our punishment that night was to take two shots each of ouzo. We were even treated that night to an evening of drinking with our Skipper while he regaled tales of him quite literally stealing ships on behalf of insurance companies as a contract pirate (yes, that’s a job title).

The next day we spent – again – in Mykonos… repair guys from another island came in to inspect and fix the engine while we enjoyed a day on the beach. Before they left they insisted on taking selfies with Dave and I… apparently all the sailors throughout the islands had heard of our blunder. That evening our Skipper said we were ready to go and asked if we would be up for an adventurous evening sail under the stars – hell yes! So again, we got to our stations, this time suited up with safety belts (lest we fall overboard in the dark), and readied ourselves for a fresh adventure.

The other skippers, captains, and boat owners gathered on the pier in stern silence to see us off. We lifted anchor, turned on the engine (success!), and left our slip. Within 30 feet, again, our engine died, the wind turned us to the side, and we came in full speed to the other side of the marina and this time we crashed right into an antique wood ship, our pulpit (the pointy end at the front) slicing down it’s beautifully varnished side with a wretched sound I can only explain as money disappearing into the night.

Panic ensued.

The Skipper yelled from the back for us to drop anchor, Dave and I scrambling in the moment to remember how to do it (push the button). Our boat came closer and closer to the concrete wharf until we rocked up against it, scraping the side.

The crowd from our original pier moved from that side of the marina to our new resting place in a way that looked like an angry mob with flashlights and sticks. One man called toward Dave and me in a thick accent telling us to get buoys, but we didn’t understand him because he was yelling “baws baws!! BALLOONS! GET THE BALLOONS!!” We told him we didn’t know what those were and that we were just tourists. This enraged him, “WHAT ARE YOU DOING SAILING A SHIP THEN?!”…. We were wondering the same thing in that moment.

Another man stepped from the crowd, he yelled that we were crazy to sail at night in this weather, what were we thinking? And then he proceeded to run his finger in an ominous line across his neck, as if slitting his throat saying, you’re going to die! You’re dead! You’re deaddddd!

The first man who had asked us for the buoys decided at this point to take over and he jumped aboard and went in search of the Skipper. Let me tell you the one thing I know about sailing, and it’s that you always ask permission to board another person’s boat. He was greeted by a fiery and very stern response from our Skipper (who was below decks trying to fix the engine) to “GET OFF MY DAMN BOAT” – which he did, promptly.

The same guys with the zodiac a few days before came to our rescue again and towed us back to our old spot. The lady on the boat next to us got on top of her ship and started hoisting buoys over the side of the ship yelling, “No! NO! NOOO!!!” Our boat came back in with a crash and added a few more scrapes to her side.

The angry mob swung back to our pier and yelled (in various languages), “Go away! You’re not welcome here! GET OUT OF HERE!” Needless to say, we were all quite shaken up (literally), and to add insult to injury, we had to lay a plank from our ship to our lovely sobbing neighbours ship to disembark via her boat as we were too far off from the pier to exit there.

We did eventually leave Mykonos the next day. Our Skipper had to snorkel through the depths of the marina bottom to untangle the mess that our anchor had left as it snagged other boats anchors and knotted up. We sailed out that afternoon in a blaze of glory, without our engine, on wind power alone … cheered on by the mob.


In summary, that was not the end of our adventure, I was wracked by outrageous sea sickness that crippled me for the entire journey to Los. Our steering wheel broke, leaving our Skipper to maneuver with what looked like a giant Allen key jacked into the floor of the boat. We did eventually make it to Los, but our boat floated away while we had dinner on shore and another Skipper had to jump aboard and save it from crashing into another boat.

Eventually, Dave and I decided to defect from the tour because of my sea sickness and the growing resentment we were receiving from the older Americans on the boat. And we were lucky that we did because the boat encountered more difficulties on its final journey to Athens and it arrived half a day late (meaning we would have missed our flight to Athens).


Looking back on this trip we could have returned and gripped that we wanted our money back, that the tour was awful, and that we had a miserable time. Instead, we look back on it as an amazing memory and an unforgettable adventure – we even gave our Skipper a 5-star review, because that guy was putting out fires left, right and centre and still had a smile the whole time. And framed in our kitchen, is the sad MEC backpack strap that started it all.

Closing note: That tour company now has a sign on their engine cubbie that says DO NOT OPEN…. our legacy!

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