I visited Cuba in 2014 when Americans were technically restricted from going unless on a “people-to-people” trip or something else official. I was not on either but had prepared enough to successfully enter and exit the country under an illegal veil of disguise. With Cuban cigars, a cigar box, and a very loud vintage Cuban sugar poster all in my carry-on.
Really, it was quite easy. I got a round-trip ticket to Cancun. Endured an overnight visit far from the spring breakers. Then jumped a flight on a Cuban airline. No passport stamp and no tags to indicate I was there. Just a bit of apprehension at customs as the handsome official paged through my passport. Bat the eyes, ladies. Just bat the eyes.
Despite the free-ballin’ approach to smuggling myself into Cuba, I still opted for a loose tour since my Spanish was— and still is— shit. Cuba Adventures was one of the only choices and it thankfully exceeded all expectations. And it didn’t operate as a severely-organzied people-to-people tour so I could experience Cuba as intended. I danced in cave disco. Rolled my own cigars in a lush plantation. Taxied to the beach in a vintage car. Stayed with locals as couchsurfing wasn’t an option. The country was as ridiculously telltale as one could imagine.
After I went in early 2014, Obama soon after made some monumental and awesome changes that allowed Americans to travel to Cuba more easily. The embargo was slightly lifted; we could bring home some of those coveted cigars and rum! Of course there were several other fun political policies enacted but the average American travel could care less. The verdict was in: time to go to Cuba. So in 2016, 4 million people did thanks to new airline routes.
Here comes 2017. And Trump. It’s all about to go to the shitter… or so Trump says. In a wonderfully classic move, our passageway to Cuba will soon be restricted once more. Because Trump stomps on kittens and rainbows. Travelers are already resigning to this shift, quite sadly. Part of this was due to the initial spectacle of visiting meeting with reality. Yes, Internet is lacking. As are gourmet restaurants outside the Havana. Because that’s what “travelers” demand. Yikes. (There will still be a pretty vague category called “supporting the Cuban people” but have to prove you went to Cuba to do something else besides sip mojitos on the beach).
So— before it really goes to hell in a hand basket— I strongly encourage you to take advantage of the changeover period and get your ass to Cuba. Need more reasons why? Stare at the 10 pictures below and tell me why not. You’ll survive without Wi-fi. Somehow.
Wanna visit Cuba before it’s too late? Trusted Travel Girl and Keep Calm and Travel will give you all the details on how to make your trip (especially as an American) possible. Rucksack Ramblings has some great backpacking tips. And of course, make sure to pack awesomely.