My travel fantasy of Cuba was filled with whimsy: spur of the moment decisions, untrodden experiences and surprises at every turn. What I found was a much more established tourism infrastructure. I think this misconception stems from the fact that while Americans are "banned" from traveling to Cuba, the rest of the world is not. Tourists have been coming here for decades, and the shared experiences in comparing notes with fellow travelers proves there is a well established Gringo Trail in Cuba. That's not to say Cuba isn't full of whimsy. Traveling there is full of surprises and you either learn to adapt to the Cuban environment or you have a terrible time. Don't expect anything on time or in a timely fashion, and always know that where there's a will and some currency, there's a way.
The guide book problem
The thing I found most interesting about Cuba is that it seemed there, more than any other place I've been, people clung to their guidebooks like lifelines. I was surprised to find lines at restaurants, reservations needed at some! Any casa in The Book (AKA Lonely Planet or similar publication) was booked. But the great thing about the casa system is that if a host didn't have room for you, their neighbor or neighbor's neighbor did. Matt and I stayed off book at each place we went, and they were all fantastic. I'm guilty of following the book when it came to my stomach most of the time. It seemed so did everyone else. We would be at a restaurant packed full of people and across the street another restaurant would sit empty. The sad thing is, the empty restaurant was probably equal in quality, just as our casas were. Whoever was lucky enough to get in the guidebook reaped the benefits. This was true of tour guides as well. However, my favorite tour guide was someone set up through our casa host in Viñales. That was the real beauty of travel in Cuba. Everyone knows someone who can get you what you need, every host became a friend.
Jineteros are an unavoidable fact in Cuba. Cubans know you're not a tourist, no matter how much you think you blend in. Just be polite and say "no graçias," don't engage and be on your way. Anyone trying to hustle you is just trying to make a buck.
I'm not sure if it's because I'm extremely over-analytic or not, but I felt a constant, dull sense of guilt while in Cuba. Since all Cubans know you're not a local, then you must be a tourist, or on business or in the country for some other reason. But no matter the reason, it means you have money. It means you have cash. And the beggars know it and the jineteros know it, so you know that they know it too. Which means that while I did try to bargain for things I knew were overpriced, like taxis, I still felt guilty about it and didn't bargain with my all. If a couple of extra CUCs were going to make or break my trip, then I shouldn't have been traveling in the first place. I imagine if I spoke Spanish my guilt might have been assuaged in that I'd be able to communicate more effectively. But, I don't, so it wasn't.
Sitting, waiting, wishing
You will wait in like. Period. Imagine that almost every professional, except tour guides and cabbies, were a U.S. Postal Service worker. That's communism. That's Cuba. It seems since the system isn't working as well as promised or hoped for, people are even more resigned about their jobs. They're going to make their government wage no matter what. No matter if they get through the whole line or only 5 people.
In the months leading up to arriving in Cuba I debated about renting a car while there. The freedom of having our own wheels was appealing; however the possible SOL scenarios were a big deterrent. Were the roads that bad? Would we run out of gas? Would the car break down? From all of my research it seems renting a car was a gamble all the way around. You could make a reservation but the likelihood of having a car waiting for you was 50/50. I didn't feel comfortable putting money down online for something I wasn't sure was a sure thing. I would recommend renting a car if you are working with a travel agent or reputable guide, or if you bring enough cash to cover the expense and are okay making the gamble of securing an available car.
Our final decision was not to rent a car. Funnily enough we met a couple our first night in our casa that had the exact scenario of not having a car waiting for them at the airport. Financially it was a smarter decision for us, we spent 234CUC on transportation total for our trip. That number came from all regional travel expenses, not including local taxis. Renting a car would have cost, from my research, about $300 each, plus gas. Again, not speaking Spanish would also have made the whole car rental thing that much harder.
From Havana to Trinidad we opted for a connectado bus. The connectado system uses smaller busses than Viazul and picks up out of major hotels. We found it more convenient for leaving Havana because we could purchase our ticket from a hotel within walking distance, Plaza Hotel off Parque Central in our case, rather than taking a taxi to the Viazul bus stop (which is 2km outside the city center). Also, you purchase an actual, physical ticket, rather than a "spot." The connectado system serves most major destinations and you can buy tickets from Cubanacán offices as well as certain major hotels (usually ones with some sort of tourist information/booking desk). Make sure to purchase by 2 p.m. the day before you want to leave at the very latest.
The rest of our inter-city transfers were done via collectivo taxis. Collectivo taxis are exactly what they sound like, rides shared with other passengers. The collectivos were usually just a couple more CUCs than the busses, but cut travel time in half. We thought they were definitely worth it.
All of our collectivos were junker cars; the AC was just the windows rolled down. And while it might not be as plush as riding in an air conditioned bus with Cuba's version of MTV on the screen, the experience felt more authentic and adventurous. The collectivo system was impressive, it's made up of local drivers that drive a specific leg of the journey. For example, from Trinidad to Viñales, we had one driver get us to outside of Havana, and then someone else took over for the portion to Viñales. Our transfer took place on the side of the highway, a make-shift bus stop if you will.
The collectivo system speaks to the industriousness of the Cuba people in forging capitalistic enterprise within their Communist economy.