One of the biggest surprises to me about being in Cuba is how much I’ve come to enjoy helping friends, family, and business clients with their travel arrangements. It started as a casual thing, but somehow in spite of my best attempts to resist it, became something more.
For me, there’s nothing automatic about it – every person is a unique and intriguing puzzle, and there’s something oddly exhilarating about matching people’s interests and means to their travel experience. Cubans are gregarious and generous hosts, and their country is over-the-top beautiful. I’m excited to help visitors discover it and always a little heartbroken when they leave.
There’s also a definite advantage to having a “fixer” on the ground. Nothing in Cuba stays the same for long. Restaurants, hotels, B&Bs, rental cars, roads – all have a limited shelf life, and if you don’t have someone to personally review current conditions in advance, who understands what matters to you, well, buyer beware. Some tour companies deal with this by encouraging visitors to lower their expectations. If I were a travel agent obliged to make block reservations years in advance, I’d do the same. But I’m not. I basically plan custom itineraries for people who know what they want, and I try to exceed expectations rather than shatter them.
I don’t do it for everyone though. The minimum requirement for my travelers is that they agree to let me help them arrange their lodging, rent a car (with or without a driver of my choice) and acquire a Cuban cellphone (or sim card) for their entire stay here. This maximizes a traveler’s time, no matter how limited, and allows me to help smooth any difficulties along the way.
Some of my friends are Lonely Planet aficionados (with great affection I refer to them as anti-planners), who prefer to wing it and rejoice in randomness. I get that, sort of – but if that’s your deal, I’d rather not be involved. In Cuba, randomness means you are likely to pay more to see less, uncomfortably. And it doesn’t mean you’re seeing anything more “real,” or moving about more independently. So why?
If you want my help, write to me (firstname.lastname@example.org) and ask me to send you my travel questionnaire. Once I have a general idea of your interests, budget and timeline, I can respond with a proposal. My itineraries also include line-item budgets that allow a traveler to come to Cuba with the perfect amount of cash to cover expenses, no more, no less, (because US credit cards don’t work here, no matter what anyone says). I can even take care of currency exchange in advance so all you have to do is arrive at the airport, collect the keys to your car, and hit the road.
Note for Americans: Trump’s arrival in the White House and subordination to Marco Rubio has reawakened the bogeyman of Cuba travel. I’ve been traveling to Cuba longer than the bogeyman can even remember, including during the age of Bush II, when the bogeyman was not as toothless as he is now. Bush II appointed judges to hear the cases of rebellious Americans insistent on traveling to Cuba on their own terms, and sometimes even fined them. There is no evidence that Trump has gone or will bother to go that far, nor is there any evidence of any nasty US customs interrogation of returning travelers, outside scattered reports of harassment at Miami’s banana republic airport. The simplest prophylactic is to avoid Miami whenever possible.
The Fifth Amendment of the US Constitution guarantees every US citizen the right against self-incrimination. In its crudest analogy, this means that although in theory you might be put on trial and even sentenced to hang (ok, not for visiting Cuba…yet), it is not your responsibility to furnish the rope. It may be helpful to think of your Cuba travel this way. Or more to the point: “what happens in Cuba stays in Cuba.”
I will furnish a printed itinerary for you to present to customs officials on your return if you feel you need one, but the only way your government is going to find out what you really did, where you really stayed, who you really talked to, is if you tell them. In the age of constant surveillance this may be a hard thing, especially for Americans, to grasp, but the US has no ability to do that kind of thing in Cuba. None. The impenetrability of Cuba’s telecom/internet system is one of the things that bothers the United States the most. Enjoy.
Am I advising that you do things on Trump’s blacklist, like stay at the Hotel Kempinski, or take long naps on the beach? (Believe it or not, you are not supposed to do either one of those things.) No, of course I’m not. But…if you were set on doing exactly that, and if a Cuban were to pay cash for your reservations, how would anyone know? Customs agents are not mind readers. In other words, you’d have to furnish the rope.