TAKING OFF

Two Friends, a Sailboat and a Series of Bad Decisions — My Wildest Travel Story

We all made it back from Cuba alive, just barley.

In my early 20s I used to waitress in my hometown until I had saved enough money to get myself abroad and then off I would go.

This time, I was off to Mexico to visit my best friend and ex-college roommate, we’ll call her Sarah, in Cancun. Our plan, to go for as far and as long as our money would take us.

We started on the white sand beaches of Isla Mujeres, just off the coast, where we met three Texans with a sailboat. After several rounds of Corona with lime, we had a plan. All 5 of us were going to go to the Cayman Islands in their sailboat. We would help crew the boat in exchange for passage.

It seemed like a good plan. We went and got groceries for everyone and off we went. Thinking back, I probably should have investigated the captain a bit more to see how much sailing experience he had, but to my 24 year-old self, he was old (at least 50) and surely if he owned a boat he must know how to manage it.

At first he did seem to know what he was doing, he taught us how to hold the boat on course and read the compass. We each had four-hours shifts steering. Both Sarah and I were assigned to the middle of the night which seemed fair as we barely knew our hosts and we felt that we owed them but didn’t want to pay for the trip with any kind of other “favors”.

My shift started alright but soon the winds picked up and it became super choppy. I managed to keep the boat on course at the expense of terribly bruised hands. I didn’t complain though, it was thrilling! The boat was tipped at an angle, catching the wind and making pretty good time.

In the morning I made peanut butter and jelly sandwiches for everyone and learned that even this basic thing was almost impossible on a steep angle. I simply did not have enough hands to hold the knife, bread and 2 jars. The sandwiches were pretty messy but they hit the spot.

At that point, I began to think that sailing seemed a lot better in my imagination than it actually was in reality.

The third day dawned bright and sunny but something was wrong, the water line was a lot higher than it had been the day before. The captain pulled up the hatch at the bottom of the boat and sure enough, it was full of water. There appeared to be a small crack in the side of the boat that let in water when we were tilted that far over.

Normally the bilge pump should have taken care of this problem but it was burned out so we were in danger of sinking. We had barely seen another boat for 3 days, let alone land, so the captain began to get panicky. This was not reassuring at all, but about an hour later we saw land.

To say we were excited would have been an understatement, Sarah and I were dancing around hugging each other but the captain, being a man that didn’t like too much excitement said he didn’t think he wanted to land there. I did some mental calculations about what direction we had been going for 3 days, and knowing what the map of the area looked like, told everyone that it had to be Cuba. The captain disagreed but had no alternative idea of where we might be, so the rest of the crew went with my idea.

At that time it was illegal for Americans to go to Cuba but I didn’t care, land was land and I’ll be damned if I was going to drown just for some silly laws. So, I convinced everyone that even if it was illegal we should go there and try to fix the boat.

The captain insisted on flying the US and Texan flags as we made our way in, and I just hoped the Cubans were not as angry with us as we were with them at that moment in history (1993). Luckily, they weren’t and bent over backwards to make sure we were OK and could travel around the country.

The soldiers who came to greet our boat, spent the several days it took for them to communicate with their superiors in another town and clear us to enter the country, on our boat playing guitars and chatting. Sarah and I were the only ones who spoke Spanish so we served as translators.

Beer was acquired and our little boat took on a party atmosphere.

Finally we were cleared to enter Cuba, the superior army officials made the trip all the way out to our boat to give it to us personally because we were the most exciting thing to happen in that part of the woods for a while. They didn’t stamp our passports because they said we would get in trouble when we went back to the States if they did, so they stamped little slips of paper we were required to give back to them when we left.

They gave us free reign of the island for as long as we wished to stay. I really miss those days when travel was less controlled and immigration officials had a laissez-faire attitude about it all.

So, now, it was on to Havana to see if we could buy a bilge pump and get back to our itinerary. One thing to know about Cuba in the 90s, was that you couldn’t really buy anything. You know those pictures you see of Cuba with those really cool cars from the 50s. Well they are not driving those from some love of retro, no, they are driving them because they haven’t been able to get new cars to the Island since Castro took over. So, they have had to just keep repairing the old ones.

So, no bilge pump to be had for love or money in the non-existent stores, but we were told we might be able to find one at Hemingway Harbor where all the boats were docked.

Sure enough, after asking around we were directed to a boat where an old American expat lived. He had been hiding out there for God only knows how long, but he had an extra bilge pump. He was also very horny and kept eyeing me up and down and saying things like “I’d like to see her on her hands and knees scrubbing my deck.”

I had to smile and pretend he was very amusing. I did that for hours while I tried to convince him to sell us his bilge pump. I finally managed to do it and successfully avoided his roaming hands when, inexplicably, the captain decided that this was too much of a hassle and we didn’t really need the pump after all.

What the hell!!!?!!

I was young though and I couldn’t convince these 2 men that they were being utter fools. The captain then in his frustration went off to find a prostitute to make himself feel better.

He found one and so, our merry band of 5 became a merry band of 6. The prostitute didn’t speak English, the Texan didn’t speak Spanish, so it was up to me and my friend to translate again. It turned out that the girl was very nice and we all went to a disco and danced the night away.

When it was time for the captain and his “date” to do what he was paying her for, happily, we discovered that in Cuba, you can not check into a hotel with a Cuban girl. Apparently they were not buying his story that she was his daughter or something. So, after going to like 5 hotels and getting the same answer, we drove her home and said goodbye. She was happy, I was happy, the captain was not.

The next morning, first thing, we headed back to the boat and prepared to go. In the evening, we were enjoying one last sunset on deck when a man in his underwear swam up and boarded. Apparently he had escaped from jail and wanted a ride to the States. We explained to him that we were going back to Mexico, not the States but he still insisted that we take him with us. We were going to be inspected before leaving the next morning, and not wanting to create an international incident, we told him we couldn’t. We shared our beer with him and took him back to shore.

The next morning we were off with a crack in the side and still no bilge pump but, the captain assured us we would be fine as long as we didn’t tip the boat at a certain angle. This seemed like the height of stupidity to me but I couldn’t think of any other way to get off of Cuba seeing as we weren’t supposed to be there in the first place.

At least we still had the little lifeboat/dinghy thing if things got really bad.

The captain, frustrated and in a mood, didn’t seem to care about captaining at this point, so he failed to tie up the lifeboat/dinghy and when we woke up in the morning it was gone. The rope had been severed in the high winds. Upon seeing this, the captain got really pissed off and began yanking things around with the sail resulting in completely tearing the main sail and rendering it useless.

So now, sitting in the middle of the high seas with only one small sail and no lifeboat, I began to seriously consider the fact that we may not make it back to Mexico.

Slowly, slowly, with our supplies of peanut butter dwindling, we limped back for days. Sighting the lights of Cancun in the distance was one of the most beautiful things I had ever seen.

With our destination in sight, we ran aground on a sandbar. By this time I never wanted to see another Texan again, and the thought of having to spend one more night on that boat was unbearable.

But, spend the night we did, because the tide was out and the moon took hours to lift us back up again. By the time we freed the boat and got ourselves docked it was the next evening. Starving and extremely grateful to still be alive, Sarah and I bid a quick farewell to the rest of the crew and ran to the nearest TGIFridays and ate our weight in burgers.

So, I survived my 20s but used at least one of my nine lives doing so. I have still never been to the Cayman Islands.

For two other survival stories, Check out this one by Ian Hanson about surviving a bus:

and this one by Walter Rhein about surviving an airplane”

I hope you all have safer but equally adventurous adventures!