Preparations for Cuba Travel

A twenty-something friend of mine popped over to Iceland for vacation with only a couple days of preplanning. If Lonely Planet and multiple internet sources are to be believed, if you are a United States citizen, your Cuba adventure should not be spontaneous. This may or may not be true, but for my first Cuba trip, planning seemed prudent. Here are my reasons: US government travel restrictions, potential language barrier, accommodation arrangements, and what I’ll call the “freak out factor.” Let’s consider each...

• US Government Travel Restriction - Unless you are planning to fly to Cuba from outside the United States—-from Canada or Mexico, perhaps, with only a travel visa (not strictly legal, but thousands do it without a hitch)—- restrictions apply. Currently, winter of 2018, solo travelers must qualify under one of twelve categories. “Support for the Cuban People,” and “Journalist,” are the two that I considered. The US State Department has detailed information about each. Unless you travel with an organized tour group, you get to figure this out on your own.
• Language Barrier - Cubans speak Spanish, and a few speak English very well. While Duolingo rates my Spanish fluency at 48% (hey, not too bad!) that's not sufficient for me to feel comfortable in the places I want to go: outside the tourist hubs of big cities, out in the countryside, little towns, and off the beaten path.

  

  Cuba! So much to see; so little time!

• Accommodation Arrangements - Gone are my days of sleeping on a thin mat on rocky ground. Twenty-something I am not! My husband and I planned our trip during peak season, which meant that the pool of casa particulares was shallow relative to off season. Finding a comfortable bed would take some preplanning. I started a month before our February trip and found an adequate selection at each stop of our journey. Last-minute Airbnb bookings work great where internet connectivity is readily available. Cuba is not this place! Connectivity is said to be sparse and sketchy. I know that spontaneous lodging discoveries can be fantastic. We did that long ago in Great Britain where we were a) driving a car, and b) fluent in the language. For the current trip to Cuba, I wanted to know exactly where we would rest our heads each night!
• The Freak Out Factor - I’ve pined for Cuba my whole life, but still might have found multiple reasons to freak out if I had procrastinated. There is a lot to think about and do ahead of time---passport, visa, travelers health insurance, exchanging money, flights to and from, itinerary, lodging, understanding and complying with US government regulations, and on the home front, a multitude of considerations from prepaying bills to what to do with the dog! 

Perhaps I'll pop over to Cuba someday. For now, I'll plan.