So they say third time’s a charm right? My third attempt to make it to Cuba became an adventure before I even got on a plane. I had a trip to Mexico planned for this week, I travel this week every year. But when I got back from New Zealand and realized I’d be doing that trip solo I decided to cancel it and book Cuba instead! I checked the hurricane season again and decided to pull the trigger. I tried to make it here twice last year and both times the trip was thwarted by hurricanes. This time I was determined. I even reserved the same AirBnB I was to have stayed in last May when I first tried to come (twice). I was ready and anxious to finally make it there. I hadn’t wanted to do Cuba alone and I had a couple girlfriends that really wanted to join me but this week wouldn’t work for either of them and I wasn’t going to be held back by someone else’s schedule, so booked it solo, making it an even bigger adventure as I speak practically zero Spanish. I had trepidations about this solo travel but then I reminded myself the strength I found in my travels last year that I never knew I had.
And then things changed. Twenty seven days before I was set to begin this adventure I met him. Our first meeting was over a protein shake after a workout, two solid hours of sitting in a juice bar and talking (do you know how hard it is to talk with blenders constantly whirring in the background?!) and I already felt the chemistry. Two days later we met again for dinner. As I told him of my upcoming Cuba trip and the fact that I would probably be completely disconnected from any communication he said he would worry about me while I was there. “So come with me,” I purred with a bright glint in my eye, amusing myself by throwing that out there. Yes, we know I like to throw a challenge.
Ten days after our first meeting, we had seen each other regularly and the chemistry was perfect, he asked me when I would need to know if he would join me in Cuba. I was impressed. This guy saw my spontaneity and was considering matching it. I told him basically at least 48 hours before I left I’d need to know but if he was really interested I should book the flights now on my companion pass so none of them sell out. By that night I had a copy of his passport, my companion pass changed to his name, and flights booked for my new companion to join me in Cuba. Who does that?! Like really, who, ten days after meeting a dude, is all in to have him join on an eight-day trip. To another country! Well, call me crazy but it felt right and we all know I do have my own kind of crazy.
Two days later he confirmed he was going and the planning had to be adapted. We were leaving 15 days later. I had already booked a farm-to-table lunch, a reading with an Afro-Cuban fortune teller, a photo shoot, and a day trip to Vinales (though that was cancelled by the tour guide that day). Brandon had already done his research and the next night we sat together and figured out our itinerary. He was down to do everything I had booked and instead of rebooking a day in Vinales we found a hiking, nature, snorkeling day trip that would take us down to the Bay of Pigs. We were set. I still could not believe this man was actually on board to join me in Cuba. I asked if he had ever had an interest before in visiting Cuba and he flatly and quickly told me no and that he was only going because he was worried about me going alone. And I could tell he meant it.
That was a Saturday night. We were jazzed. Anxious and nervous but equally excited. I had mentioned to a woman who works in my office building that I was going to Cuba. Monday morning she swung by my office, “Did you hear about what happened in Havana last night?” Uh, no. “A tornado tore through the town!” WTF?! I quickly harnessed the power of the google and found that, indeed, a massive tornado did rip through Havana. At least 3 people dead and 200 injured with 3,500 homes destroyed. Oh, and possible water system contamination and tons of infrastructure down. Ugh. I texted the article to Brandon practically with an SOS. The universe was telling me something. I was not meant to go to Cuba. It did not seem like this trip was meant to be. For the third time, a natural disaster has thwarted me from visiting this forbidden island. Our trip was less than two weeks away. Long story short, Brandon and I talked that afternoon and agreed that it didn’t seem like a good idea to go so soon after such a major disaster. So we cancelled the entire trip. And booked the Hyatt Ziva Montego Bay all-inclusive resort for the week instead! We had both always wanted to go to Jamaica so why not?! I was not giving up on having a trip. Now I was even more determined than ever to make sure a trip happened; both because I love my adventure time and, now that it was really sinking in, because I was eager for the time with that man.
I have to say that AirBnB was awesome. We had booked all our experiences with them and, even though they had 30 day cancellations, I simply had to make a two-minute phone call to AirBnB customer service and explain that our trip was cancelled due to a natural disaster. Within two days they had completed claims on each experience and refunded all the money.
Jamaica would be a different kind of a trip. More of a lay around and relax on a beach trip. A vacation, not an adventure. But we could book an excursion every day so I didn’t get bored. I have about a ten minute tolerance for laying idly on a beach before I’m going crazy without something to do. We spent a few days researching excursions. And researching the country, neither of us really knew much about the island. We both knew it was dangerous but we didn’t realize just HOW dangerous it really was. It’s scary dangerous with one of the highest murder rates per capital in the WORLD. We couldn’t decide on a single excursion to book in advance. We decided we would just book stuff once we got there. This was hard for me to swallow because that meant we were going with no itinerary but beach time. But this was an OUR trip now and not a ME trip. I wasn’t overly excited about this trip. The disappointment over cancelling Cuba, yet again, lingered and the excitement to be in Jamaica faltered. I honestly started to worry if being stuck at a resort for a week would make me crazy cranky and how badly that could be for my time with this man. I was not overly excited for this trip. And neither was he as the sheer danger of the island made him uneasy.
And then it hit me in the middle of the night. Three days before we were to leave for Jamaica I could not sleep. I normally do have insomnia but it was extra bad that night. I had tried to jazz myself up for Jamaica by buying three hot designer bikinis, but even that didn’t help. And I hated that Brandon wasn’t excited either. I realized that, for me, this trip had stopped being about where I was going and had become about who I was going with. This revelation was exciting and scary, a new sensation for me as a feeling. And then at 1:30am it hit me. We didn’t HAVE to go to Jamaica. Why should we make ourselves go somewhere neither are excited about? What about Belize?! We could go to Belize. I had a 30 day cancellation on the resort I’d booked in Jamaica so it was too late to cancel but I just knew that I’d find a way out of it. And I even felt that if I couldn’t, it would be worth losing the money on the week at the resort then going. That’s when I knew we really shouldn’t be going. Any why not Cuba actually? I searched for as much news as I could find on the tornado aftermath and found an article just a couple days old. Yes, 6 people were dead. Yes, many injured. Yes, 3,500 homes needing to be rebuilt. But, the infrastructure had been restored. I had also heard something earlier that day, a line in a show, with the reminder that if you are always waiting for the perfect time nothing will ever happen. I was convinced. I shot off a quick 2am text message to Brandon. “I know you probably think this is insane but why don’t we cancel Jamaica and rebook Cuba?! The infrastructure has been restored!” By 2:15am I had confirmed that the flight and all experiences we had wanted to do were still available. The apartment we had rented wasn’t but there were hundreds on AirBnB. This is what I wanted.
The next morning I welcomed Brandon to my kind of crazy and explained my rationale. From the start he had said he was cool with whatever I wanted to do but I didn’t want to bulldoze him. We talked that afternoon and I made sure he was fully supportive of the idea. He was. Within half an hour I got out of the resort in Jamaica (I love you Hyatt), changed our flights from Jamaica back to Havana, and rebooked all of our experiences. Except the farm-to-table lunch. Mind you, this was all within 72 hours of when we were leaving on this trip.
I was excited again. Ecstatic. Thrilled. I had another “who does this?!” moment about myself and realized that I love that about myself! I do that. I’m sure people think I’m a touch insane but I only get one life to live. Brandon came over the next night and we picked a new place to stay. He convinced me to stay in the more “luxury” neighborhood of Vedado instead of the more humble Habana Vieja. We had two nights after that to get ourselves ready.
Before we knew it, Saturday had come and it was time to fly! We would fly to Fort Lauderdale, Florida on Saturday, overnight there, and leave for Havana the next morning. Here we go. The first leg of our flight was a short hop to Denver. On the plane we began looking at AirBnB and somehow got onto the list of other Cuba properties I had saved. And lo and behold, a beautiful villa on the beach that had previously shown as booked had two nights free. Brandon saw the twinkle in my eye and agreed it would be amazing, he had been looking at beach houses all along. I pondered out loud that it would be so easy, we could keep our place in Havana and just book the villa for one night, all we would need to do would be pack an overnight bag to go with us! And just like that, amid some crazy turbulence in the air, I pressed the button and booked a beach house for Monday night!
The second leg of our flight was four hours but the time passed quickly. We had a great flight attendant, Stevey Ray, and, at my desire, Brandon taught me how to play chess. I’ve always wanted to learn but have never even tried. While the boy is amazing, his chess teaching skills could use some sharpening. I ended up writing out my own notes as a cheat sheet on a Southwest cocktail napkin. As we played, new rules kept popping up that he had failed to mention before. I won the first game, got my booty kicked on the next, and then started to figure it out and we came to a draw after a long third game, where I ended up with just my king on the board and he still had about six players out there.
Just shy of 10pm we finally made it and checked in to the Hyatt House for the night. We had some super subpar McDonalds because it was close by and I was getting hangry. Our priority was to get a good night’s sleep since neither of us had slept fantastic the night before and the next morning we were off to Cuba!
Taking On the World 
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