Keith and I have been wanting to visit Cuba for awhile. When we decided to travel to the Cayman Islands in early August with a stop in Cape Cod towards the last week in July we had a few days in between that we needed to fill. That is when we decided that all four of us would visit Cuba. 

We ran the idea by the kids. Needless to say it wasn’t as well received as maybe a trip to Paris would have been. The first reaction was “why”? We don’t want to go. It is hot and humid and there is no wireless. Oh the first world problems. We then tried to explain how they would thank us in 20 years. A curious look back at us, like no we will not thank you in 20 years. We just don’t want to go.

This was one of those family situations where we ran our house like an authoritarian oligarchy, the tickets to Cuba were purchased and the travel plans began. No veto power for my kids. 

My first stop for everything travel related is Trip Advisor. I scour every forum, every review. I read between the lines, I look for angles. I need to know everything. I especially need to know if I am making a good choice when it comes to accommodations. My requirements differ from Keith’s (which is a blog post unto itself).  When I’m making my travel plans I am consistent,  I am looking for luxury accommodations set within the culture of where we are visiting and not in the touristy center of things.  Not always an easy find especially within our budget. Keith always jokes that I require a certain thread count for my sheets. Yet strangely, I always want to figure out a way to mix culture, some luxury and the feeling like we are really getting to know the locale. Yes I am a walking contradiction.

Visiting Cuba with our two girls meant that I needed to find the right place to stay. We wanted to be in a central area but not too touristy. We wanted to feel like we were in Havana not a dated state-run hotel or dilapidated old home, some modern conveniences while still feeling the Cuban vibe. Sounded reasonable. 

Air BNB to the rescue. I went through every listing with a fine tooth comb. Read every review. There were a handful of properties that met my requirements. 

I didn’t act fast enough and lost out on my first choice. A few days passed and I had to make a decision. Why did it seem like such a big deal? We had our tickets, we needed a place to stay. I showed the listing to the family, everyone agreed it looked perfect. Back to the household democracy. So I pulled the trigger on my second choice. It checked most of my boxes, 2 bedrooms, it was in Old Havana, we could walk to just about anything, restaurants right outside the front door, mostly 5 star reviews, it had A/C in the bedrooms, updated bathrooms, high ceilings and the coveted balcony. Done. 

The week in Rhode Island and Cape Cod came to an end, we were at the Boston airport checking in for our flight to Havana. We tried to use the United check in kiosk, but the message said to see an agent. We were then escorted to a special line to check in for the flight. Yikes. I became paranoid. The stress of Trump’s decision in June definitely weighed on me as we stood there feeling guilty of doing something wrong even though we hadn’t. The agent took our passports and then disappeared behind a closed door. Back she came armed with some questions. After a little back and forth, we were handed our boarding passes and off to the security line. Was it smoke and mirrors? Did the airline care if we were headed to Cuba? Were we in the clear?

Apparently we were. From Boston we flew to Newark. Once at the gate, we had to pay the $50 + $25 fee for the tourist card for Americans traveling to Cuba. Interesting. Seems a little steep, a surcharge that you know somewhere someone is benefitting from. Was it the US government? The Cuban government? Who splits this fee? Talk about misinformation and not understanding whether or not it is really ok to travel to Cuba. Well apparently while all of this misinformation is flying around someone has figured out a way to capitalize on the confusion by adding on this fee. An extra $300 just to enter the country. It better be worth it!

When we landed in Havana we passed through immigration. We were traveling as a family of four. When it was our turn to give our passports and immigration forms, they asked Keith to pass through separately. They grouped my two girls with me. They individually photographed each of us (with a lovely sticker of a Cuban flag stuck to the wall behind you so that I guess you can never deny where you traveled to), stamped our passports and sent us through to rejoin Keith. 

Another line followed. Now all of our carry on bags had to pass through security. Then on to baggage claim. It seemed as if one person was loading the bags one by one onto the conveyor belt. As slow as the process seemed, it was still more efficient then the bag delivery at Phoenix Sky Harbor (slowest). I was so thrilled to see bathrooms available in the baggage area, with the 3o minute ride to Havana ahead of us, this was a necessary stop for all of us. Before we passed through customs, we changed some dollars into CUC in order to be able to pay for the taxi. Following all the advice I had read on TA!

We walked out of the terminal to the curb, past a bunch of people hawking taxis and found a yellow taxi. We asked him ahead of time how much it would be. He said 30CUC which is exactly what we had expected. Before we drove away, I asked him if I could use his cell phone to call our contact for our Air BNB. 

Success. We were off.