If ever there was a destination on our bucket list that required carefully making sure all our i’s are dotted and t’s our crossed Cuba is most definitely it.

As American’s Cuba has been lingering in our collective thoughts as a dream destination for as far back as Dj & I can remember. For the longest time we assumed, that it would always stay just that, a dream. But to quite Bob Dylan, “the times they are a changing…” and at the same time, they might be changing right back.

Here in lies a predicament for us. While it may seem like we live a life of perpetual travel, we don’t. Wouldn’t it be nice if we did? We still have jobs, a home we affectionately refer to as basecamp, and the same everyday commitments that everyone else is juggling.  Our lives are busy. We have to work extremely hard, and carve out time to make our travel dreams happen. Unfortunately time isn’t always on our side. With changes in the political atmosphere in the US the recently “opened door” to Cuba maybe slamming shut, and soon. Most of the time we’re juggling pros when it comes to schedules, this time, the time window just wasn’t in the cards for both of us to make this dream happen… so the for first time in as long as I can remember I (Katie) am traveling without my partner in crime! This should be interesting…

Sit back, and get comfy kiddos this is going to be a long post- there’s a lot of information worth sharing, that took literally days of digging through the deepest bowels of the internet to find.  I promise, I’m not going to drone on just to drone- to make it simple I went ahead and broke this post into sections so if you’re looking for something in particular just scroll on down, it’s probably here!

So here’s the deal with veturing to Cuba…or in the very least everything I’ve discovered so far…

Getting There:

There are two basic ways to get to Cuba, by air or by sea. When weighing my own travel plans to Cuba, I did ALOT of thinking on the pros and cons of each.


By air..

  • PRO: You can stay as long as you’d like, within reason of course. Giving you plenty of time to wander and explore. This means broadening your Cuba experience and getting outside of Havana.
  • PRO: You can go whenever you choose. No need to stick to pre decided dates, as long as you can find a flight you’re good to go.
  • CON: There’s a lot of shuffling. International travel requires extra thought for sure, but this is even more true when trying to arrange a few days of exploring in a place like Cuba. With highly limited internet access getting in touch with people to book actives, hotels, etc. can be a bear.
  • CON: Sticking to a budget. I can’t tell you how many times we’ve missed going someplace because the flights for our travel window were just too expensive. This of course can be worked around assuming you know well in advance when you’re traveling ( thats def. not always the case for us). I’ve heard that accommodations are very reasonable in Cuba, but that flights can get pricey.


By sea..

  • PRO: Budget management. If you do your research before taking a cruise, you can easily get a clear picture of how much your final costs are going to be. This is especially true because food ( and sometimes) alcohol is included in the cost of your trip.
  • PRO: Cruising is easy. You get on the ship, unpack your bags once, and you’re good to go. No need to worry about booking a hotel room, changing locations over and over, packing power converters,  or all the other moving parts that go into travel, the list goes on and on.
  • CON: Cruising is easy. Maybe it’s just me but I personally think that takes something out of the experience. Travel shouldn’t be easy. It should challenge you, you should grow from it- am I right?
  • CON: You’re stuck going wherever the cruise ship docks. If the ship only goes to Havana, you’re only getting to see Havana.
  • CON: Time. Your cruise ship has a schedule which means you have a schedule too. No matter how you cut it, your time is going to be limited, and you’re likely not to get to see and do everything you want.
  • CON: Cruise ships. This is entirely personal opinion, and I certainly don’t mean to offend anyone but through I’ve noticed wherever cruise ships roam, culture dies. On the same hand, cruise ships bring money which helps economies grow and people thrive. It’s a double edged sword I supposed- I’d love to hear other peoples thoughts on this!

Want to know what how I’m getting there? Drum roll please…. I am going by sea! Are you shocked? I am too.


Boarding To Cuba

If you saw our video on Crossing the Canadian Border in a RV then you know I’m a little bit of a nervous nelly when it comes to being sure all my documents are in order- I think this stems back to a time I lost a connecting ticket on a trip ( a travel horror story for another time). The truth is this should be common sense. Whenever you travel outside of your own country you need to make sure your covered. How bad would it suck for not just you but also your traveling companion if you got somewhere and realized you couldn’t keep going because you were missing something? Don’t be that person. Here’s what you’ll need for traveling to Cuba:

  • PASSPORT: This should be a given, but I’ll list it anyway. Make sure that puppy is up to date, signed, and stowed away in a safe location. Great news, as of this moment ( while I type this) American’s can proudly get those Cuban stamps in their passports, now thats something to smile about!
  • ID’s: obviously to go along with your passport you’re going to need an additional form of picture ID, a driver’s license or military id will do the trick. Again, whatever you do try and don’t lose these, they’re kinda important!
  • COPIES: I always make multiple copies of my passport, driver’s license, and health insurance card when we travel. I stash them all over, I’m not kidding. In the case that I accidentally misplace one of the original documents I want the security of knowing I have back ups. The age of technology helps a lot too with this…I take pictures of them, that I store on my phone and send to my emergency contacts, and keep photocopies at home,
  • VISA: This is a bit of a complicated one, so I’ve given it it’s own section. Scroll on down to check out the details but for now, know you need one BEFORE you leave the US for Cuba ( if you’re an American Citizen) and that it’s going to add extra $$$ to your trip.
  • Cuban Health Insurance: I’m going to be real honest with you on this one. I don’t understand quite how this works. I think that this probably has to do with the structure of the government and making sure your costs are offset in the case that you require medical care. Bad travel advice coming your way- I’m not sure how much this actually cost because it was included in my ticket costs- this will be the case for most airlines and cruise ships traveling to the country. In the least do your due diligence and ask when you buy your ticket to make sure you’re covered.

Visa Requirements ( For American Citizens): 

Ug. Visas. So here’s the deal, while American’s are now allowed to travel to and from The US to Cuba ( no more going through Mexico, or Canada!), you’re not really free to move about the country and do whatever you want. Your visit must fall within one of 12 Categories approved by the Office of Foreign Asset Controls (OFAC). You can pick whichever category you think suits your travel purposes best, and no laying on a beach drinking mojitos isn’t a category, bummer I know… but as Rick Steve’s said in his Youtube Video about his Cuba trip what it all boils down to  is, “pick a reason, and stick to your story”.

Let’s chat about that for a minute. We chose to travel under a “people to people” meaning our visit should focus on education and enhancing relations with the Cuban people- vague, huh? Activities that qualify for this are cigar and rum factories, museum visits, and guided city tours, it’s pretty general. The most important part of all this is you are required to document your visit ( keep receipts, take pictures, and a detailed list of what you did), and be able to provide justifiable reasons as to why, as well as keep all documentation for up to 5 years after your visit.

Just remember you WILL NOT be allowed to board a plane or ship bound for Cuba without this documentation.

So how do you get one of these handy dandy licenses? You have to apply for them through the US Department of Treasury. We were very lucky, as we were able to self-certify through the cruise line and they applied for the Visa for us.  I have heard that some airlines will do this as well. Check and double check  and give yourself plenty of time to chase your tail, if you need to get one on your own. We paid $75 through Norwegian Cruise Lines to get ours squared away- I’m sure they cost less if you apply for  one on your own.

If you’re still stressed and want the official deets you can get them here.

Money, Money, Money:

I am certain that throughout this planning process, I have stumbled across the phrase, “In Cuba cash is king” about 4 billion times, it’s true I have- That also leads me to believe its something I should be paying attention to.  So pay attention I did, and this is what I’ve learned so far… pay attention.

  • You Must Have Cash: Repeat after me, there are no ATMS in Cuba. If I am an American, my credit and debit cards will not work. I must bring cash, I must bring cash. I must not misplace cash, and I must bring cash.
  • Cash Exchange: There are 2 types of currencies in Cuba, the CUC (official tourism dollars) and the CUP      (the Cuban Peso). As a tourist you ARE NOT permitted to use the Cuban Pesos, which means you’re stuck with CUC. The good news if you’re an American $1 is equal to 1CUC- easy to keep track of. The bad news if you’re an American is that while there is no exchange fee for all other forms of currency (Euros, Canadian dollars, etc.) to exchange American dollars will cost you 13%. One school of thought is to exchange your US dollars to Euros before leaving for Cuba, but doing the math to me that doesn’t make sense given current exchange rates. So while I don’t like the idea of losing 13% of my cash, it is what it is.
  • Take an Educated Guess: Once I resigned myself to the idea that 13% of my cash will instantly be gone, I had to start seriously thinking about how much I wanted to spend while in Cuba. The way I see it, there’s two ways to approach this, 1) set a budget and stick to it no matter what $200 max not a penny more OR 2) list out the items you think you want, do some googling to get rough estimates of costs, add it all together and you’ve got a budget that covers your wish list. I’m going for option #2. The only problem with this is anything leftover before I leave will need to be spent and or re-exchanged at another loss of 13%. Hmm…
  • Check your change: I’ve read about quite a few cases of folks making purchases, stuffing their change back into their bags, and later realizing that instead of getting CUC’s back they were given CUP’s which are not even close to equivalent in value. Check, check and double check.

Cultural Awareness:


This one is pretty important to me, the last thing I would ever want to do when traveling anywhere, is to offend the people who live there. I’ve dealt with nightmare tourists before and I certainly don’t want to be one.  The cuban people are known world wide to be a welcoming a friendly bunch, let’s keep it that way!

  • DO: Tip, this is always something I research before traveling to a new destination as it isn’t common practice globally. Turns out in Cuba its a big yes, so don’t forget to drop your sever, maid, and tour guides a few extra CUC’s
  • DO: Bring along a few goodies. While Cuba is one of the most educated countries in the world, due to political issues ( both in and outside of the country) they have struggled economically. Food and basic nessecities are government controlled and rationed. Bringing a few extra goodies, not accessible in everyday goes a long way to say thank you to the locals. We’ve done this before in other countries we’ve visited and received a lot of gratitude for it.
  • DON’T: Blow your nose in public, this is considered extremely rude.
  • DON’T: Flaunt your wealth. Consider where you are. Cuban nationals on average receive a stipend of $20-$40 per month to live off of. Something to consider.
  • DON’T: Speak negatively about the government. It is illegal for Cubans to speak against their government. Starting up such a conversation could not only get you in trouble but also whoever it is your speaking to. Keep your thoughts to yourself, and maybe share them with us when you get back- I’d love to hear what you’re thinking!
  • DON’T: Do drugs. This should be pretty basic right. But did you know Cubans can be sentenced to death for drug charges? Keep it clean people, no need to invite trouble.

Security & Safety:

It’s pretty typical, when people hear the words, “solo travel” they tend to panic for you! Well rest easy my friends, I am not taking this trip on my own. I have conveniently managed to convince a good friend and fellow travel addict to wander along with me on this one.  Worry not.

Wether you’re traveling alone, with your partner or a friend, when you’re away from home you want to be careful no matter where you are.  I think there are a lot of concerns and perhaps misconceptions about safety when in it comes to traveling to Cuba, the reality of keeping safe is bad people are everywhere. Be diligent, keep a hold of your belongings at all times, and make smart choices. It’s that simple.

I’ve researched this topic pretty throughly, more than enough to be satisfied with my intel. As far as any EXTRA safety precautions, this is what I’ve discovered:

  • DON’T: take pictures of government officials and or buildings. Just like you ( or in the very least I) wouldn’t be brazen enough to snap photos while checking in through airport security, it’s the same in Cuba. In the new world we live in officials like to know that the gears that keeps things turning are as safe as they can, taking pictures of these places and people could potentially jeopardize that. No need to get yourself in trouble. Just put the camera down.
  • Wherever large groups of tourists flock to, pickpockets abound. This means gentlemen, back pockets aren’t the best places for your wallet or your cell phones. Ladies, don’t put your bag down, keep it in your lap of on your body at all times. When living abroad a few years back there was quite the stir when the bottoms of travelers purses started getting cut open and their belonging stolen literally from under them. If you’re worried line your bag, I garuntee you’ll notice someone trying  to saw through a thick plate of plastic.


Whew! And there it is! Literally 3 weeks of research that sent me around the internet and back again to find, all neatly compiled into one location! I hope this helps you start thinking about planning your own Cuban getaway!

Got tips? Did I forget something? Please, please, please let me know! Drop a comment below! If you enjoy these posts, or find them helpful please share our website, like us on Facebook and follow along on Instagram (@venture_wild). We’re happy you’re here and we’d love you to stay!

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