Pyrodes has already told you how to sneak into North Korea (look here). So, it seems fitting to continue our series on lovable misfit nations with a short guide on how you can travel to Cuba, that beach resort of the future that sits just 90 miles south of Miami. Now, for our non-US readers, you can just hop a plane to Cuba and have a good old time in the fun and sun, so this post is not for you. Skip ahead, or have a coke and a cupcake. For the rest, we have to tangle with the fun that is the Cuban Assets Control Regulations of the US Treasury, which enforces the fine points of an embargo older than time itself. But, thankfully, there are ways around, and thousands of Americans find them each year. Let’s explore our favorites, from religious excursions to rafts after the jump….

In the old glory days of the embargo, Americans happily found there own way to Cuba through various means, but since the advent of the Bush administration, the government has gotten much more prickly in its enforcement of the law, handing out $7,500 fines to every tom, dick, and harry who heads to Havana. So, let’s figure out some work arounds here with our five ways into Catro’s backyard.

1. The Classic: The classic way into Cuba is to fly to Canada, Mexico, or the Bahamas, and then find yourself a plane to Cuba. You’ll have to find these routes once in your Non-US launching pad because even our beloved travel websites, from Orbitz to Kayak, will give you error messages if you type in Havana as your destination city (go ahead, try it). A note: this method is easy and works, but you may be slapped with hefty fines on your way back if you spent a dime in the communist netherworld of the Caribbean. There are ways to improvise though.

2. The Letter, not the Spirit of the Law: The Embargo prohibits you from spending money in Cuba, so why not just spend it elsewhere? There are a number of growing tour groups that offer prepaid, all inclusive Cuban vacations for Americans. All of your money is spent beforehand and in Canada, not Cuba. Problem solved, right? Well, maybe. It is unclear at the moment how this go-around will be prosecuted, but hey, if you have a lawyer and love fighting The Man, then go for it.

3. Go Gilligan: Cuba is a mere afternoon hop from the Florida Keys if you have the right kind of boat, and there are numerous folks in the Florida back alleys who will take you. It used to be a fairly common route for American sailors, but as this article suggests, W has liberalized the standards for preventing ships from crossing into Cuba. You can still take your chances, as some still do, but watch for the Coast Gaurd.

4. Go Legit: Easier Than You Think: Since the US has cracked down on the unofficial routes into Cuba, it has also increased approvals for the official routes, which is good news. Today, you can find any number of religious, humanitarian, and academic reasons to go with small groups, and, once there, have a good old time. Your reasons can be as simple as learning the language, exploring Cuban art, or helping build flats for the poor. Your imagination is the only limit. The bad news is there is some planning involved, as you must apply through the Department of Treasury (look here), but the piece of mind it gives you when coming through US immigration on the way back may be worth it.

5. Go GITMO: You can always get sent to GITMO, either to the base or the prison on the base. Both have their unique adventure experiences and provide fully paid trips for their residents. Pyrodes has another post coming up soon about chilling at GITMO, so we’ll leave a further exploration of this topic until a later day. Until then, we’d strongly urge one of the first four options.

Buen Viaja and Happy Travels.

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