The embargo will be lifted sooner than later, so here's how to get to Cuba before the US annexes it into a continuation of Florida.
This month, the US opened an embassy in Cuba for the first time in over 50 years. Just last Monday, the US further loosened travel regulations to Cuba; however, it is still illegal for most people to visit the island, an offense that remains punishable by a massive fine and jail time.
Thankfully, there are several approaches and loopholes to get anyone to Cuba, either working within or around current laws, and we're here to tell you about all of them.
Because we "care."
1. The 100 Percent Legal, Goody Two-Shoes Approach
This approach is the most time-consuming, yet least likely to land you in prison with a bunkmate named XTigerX. See, the U.S. Office of Foreign Assets Control (OFAC) allows individuals to apply for an application to visit Cuba so long as their planned visit falls with 12 categories. These 12 categories of legal travel include: “visits to close relatives, academic programs for which students receive credits, professional research, journalistic or religious activities and participation in public performances or sports competitions.”
The application process takes about 40 days, so if impulsivity isn’t an issue and you fit a category this might be the route to take.
Apply for a license here: https://licensing.ofac.treas.gov/Apply/Introduction.aspx
However, keep in mind that US citizens still can’t take commercial flights to Cuba even with a license through the OFAC. Right now, flights between the United States and Cuba are operated by expensive charter companies, so you'll still have to fly in through another country if your dad didn't invent Advil.
2. The Technically Illegal Beyonce and Jay-Z Approach
According to the OFAC website, “as long as the trip falls within one of 12 purposes, Americans can go to Cuba without having to apply for permission, in the form of a license, from the government.” That leaves interpretation of the 12 reasons pretty broad, and as noted by Robert Muse, a lawyer specializing in U.S.-Cuba relations law: "If somebody wishes to travel to Cuba and they “can’t think up a way to fit into those categories, they are not trying.”
This means you and your friends who are ‘participating in public performances,’ may need a fake step-team name to qualify for a Cuban vacation semantically-speaking, but you’re, more or less, covered.
What we're saying is … pretend you're in a band.
With this approach, individuals will have a hard time landing a flight through a charter company without an actual license … but there’s a way around that as well for those so inclined. Scroll down.
3. The 100 Percent Illegal, ‘Fuck the Paperwork, I’m Going to Cuba Tomorrow’ Approach
So the ‘step team’ broke up and you still want to party in Havana. There’s a scheme for that. It’s nearly impossible to book flights directly to Cuba online because of the existing imposed US embargo. It is, however, super easy to book a flight to and from Cancun on nearly any site.
After you select your flights in and out of Mexico's whitest party city, buy a Cuban Visa (they are about $25, according to Triphackr) and book to and from Havana at the airport once you’ve landed in Mexico.
With this approach, the passport agents in Cuba will have to stamp your travel Visa, not your US passport, further minimizing the evidence of your Cuban excursion.
This approach is also possible through other third party countries, such as Canada, Cayman Islands and the Bahamas.
4. The Wild Card/ Kenny Powers Approach
Bring a back-up fuel tank and simply jet-ski to Havana from Miami. Distance: 90 miles, travel time with a Black Edition 360 Sea-doo: 1 hour and 20 minutes. Your call…
Cuba is an incredible place and Havana is like no other city on earth. Once the embargo completely falls the completely unique culture of Havana will change, so go sooner than later. If you need a last minute alibi at customs just say "Journalism," (natures perfect excuse for debauchery) and that you're working on an article entitled "Beer Vending Machines in Havana*: A Rooster Exposé." We’ve got your back.
*Yes, beer vending machines exist all over Havana and they are wonderful.