The next big journey – visiting Cuba, Mexico, and New Orleans
Once again, I am right in the middle of travel planning. My next big vacation will be in April. The most extended trip ever so far. A whole month, from Easter to May. It will be a mixture of traveling to good old and known grounds in name New Orleans, and two entirely (for me) new countries: Visiting Cuba and Mexico!
*This article contains affiliate links. That means that I will earn a little commission as soon as you click and order anything from that site. It will help me to fund this website.
Pin me for later!
Traveling with a fulltime job
If you are a regular visitor, you already know, but if you are new on the blog, you might not know yet. I still work full time, a more or less exciting job in the finance department of an insurance company. Even in Germany, the absence of one month is quite unusual.
More about traveling with a fulltime job, you can read in my recent post right here!
How to deal with your Boss
The negotiation with my boss about this extended absence from office life was hard, and it took me a lot of effort and compromises to get his “yes.” Eventually, we agreed that I work the first week remotely (yee-haw, this is what comes to a digital nomad life pretty close 😁). And for the rest of the time, I will have a look at my emails at least once a week, just in case anything urgent will happen during that time. The agreement is pretty cool. For my employer, it means that I will be available and get my work done (mainly, because it is not only month close but also the end of the first quarter. Extra important for the company, of course). So good for them and good for me. I have the opportunity to be in a different country and already can enjoy a sort of vacation. At the same time, I can save some holidays, too. What else can I ask for in regards to a fulltime job? My mantra is: “You will never know until you do it”! That is why you always need to ask if you want to know if something works out for you.
Anticipation
Back to the roots
My anticipation is enormous. New Orleans is the place where everything began. It is the first destination, where I traveled just by myself. Going back to New Orleans and already know a few parts of the city is a little bit like coming home. At the same time, I cannot wait to discover other areas and see different sites of the town.
Explore new countries
But I also will discover two more countries. Visiting Cuba and Mexico will be the first time that I travel to Central- and South America. No wonder that I am already freaking out about all the things which could go wrong. I can remember that I felt the same way when I prepared my first solo trip a couple of years ago. It was so exciting to do everything on my own and a bit scary as well. There were so many points and questions, which I had to find out before I could take off. So it is now.
Things you need to know before visiting Cuba!
In 2014, when I planned my first solo adventure, I prepared everything in advance. Point after point, I checked off of my to-do list: Visa, flights, things to do, etc. Notably, for visiting Cuba and Mexico, I do the same now. But this time, I am a bit more experienced and know which things I have to have an eye.
For the examples mentioned below, I took my self as an example. I live in Germany, and I am German. It does not mean that all the details are valid for all other citizenships. Therefore, if you visit Cuba your self, please check the following points for your unique situation.
Pinning time
1. Check travel documents
The first thing you should do is to check the requirements regarding your travel documents. Dependent on where you are registered, there might be a lot of differences. For instance, in my case, I need to renew my passport so that it is valid for at least six months after my stay in Cuba. The same requirements apply to Mexico. For the US, it would be easy, as it is enough when the passport is valid for the actual stay.
2. Check visa or similar documents
For visiting Cuba, you will need a “Cuba-tourist-card.” The trick is to get it before you fly in. It will not be available at the arrival airport or the border control. There are several possibilities to get this card. You can order it on for specialized visa providers like “Cubavisa*.” You can also get it directly from your local Cuban embassy. Another possibility is to ask a Cuba-specialised travel agency or at a travel agency at your home airport. It is essential to have it before your actual stay in Cuba. Mexico is a bit easier. You also need a “tourist-card,” but it will be available on the plane or at the border.
3. Check entry requirements
Because of the rigorous US requirements, it is not that easy to travel from the US to Cuba. There are twelve exceptions. You can try to apply for a vis with one of those reasons (e.g., educational stay, journalism, family). Unfortunately, tourism is none of them.
Because I am in New Orleans already and do not stress myself out with a super complicated visa applying process, I adjusted my plans a little bit. That is why I will stay a couple of days in Cancun, Mexiko.
However, please check US regulators in advance to make sure if there are any special and critical restrictions.
4. Check your Health Insurance
Cuba requires proof that you have health insurance that covers all medical help in case you need it. Costs you probably could have, like hospital stays, costs for visiting a doctor and so on. So make sure to check with your insurances if all these things, especially in regards to Cuba, are covered. Request an insurance certificate, which confirms that everything is covered, ideally in Spanish.
5. Check Immunization
Make sure that you have all necessary or suggested immunizations (e.g., Typhus, Diphtheria, Hepatitis A & B). In doubt, ask your doctor what exactly is useful.
Bonus tip: Check if your Health Insurance covers the costs of the immunizations and if you can get a refund. If not, then ask them for confirmation so that you can try to get it back within your taxes.
6. Check Cash requirements
Make sure that you have enough money for your stay. Cuba requires at least 50€ per day for the whole stay. A certain amount of cash is always recommended. You never know where and when you find a working ATM or a bank.
Bonus tip: Make sure that you take a proper credit card with you. In general, I have good experience with Visa. It will not be a problem if you have a second one, just in case the first one has any issues. Maybe to tell your bank or credit card provider that where you will go. It happened twice that my bank blocked my credit card after using it during one of my trips because they thought somebody, has stolen it.
7. Transportation
a.) How to get there?
Do not forget to look for flights or any other possibilities to get there. Book all at once, separate the flights, consider stopovers here or there, try to figure out when it is the best time to book, etc. There are various opportunities to find the best flights for your circumstances.
b.) How to get around?
Do you prefer public transportation, a rental car, or do you want to stay in one place where any transportation is unnecessary? As I would love to travel around the island, I need to check what requirements exist for a rental car. For me, it would be the most flexible, independent, and convenient way to get around. So I also need to check any requirements regarding my driver’s license.
If you consider renting a car, book one as soon as possible. It seems that rental cars are booked out very soon.
Bonus tip: Do not forget to print out your documents, the rental confirmation, etc. The rental car companies are usually still very “old school” and require paper.
8. Language and Culture
Try to prepare yourself with some basic words in the local language. I have the experience that in many countries, outside of tourist areas, English is very poor in general. Just in case, also check if there are any special cultural requirements. For example, it is a difference to travel to Cuba or an Arabian country, at least regarding which clothes you can wear.
9. Check weather and climate
Check weather and climate conditions first, before you pack your suitcase. You do not want to carry around a too-heavy bag or other unnecessary stuff.
10. Things to do and what to visit
For me, this point is always the most fun one. Read about the things to visit. Find out what to do and which food I have to taste. Clicking through the beautiful pictures on Pinterest and read through all the articles and posts, which already exists. Feeding my anticipation for visiting Cuba and build my bucket lists. What do you think about a sightseeing tour in an old fashioned oldtimer*? OMG, with every little point which I can tick off my expectation grows. I cannot wait until I can grab my stuff and head to the airport.
Pin me!
I so want to go to Cuba.
Good for you for finding a way to make the trip happen that works for you and your boss!
Thank you Cassie, I´m really looking forward to this trip! 😀
Great post, I’d love to go to Cuba but there are some hurdles that need to be crossed first!
I’d love to go to Cuba! I think it’s one of those countries where you can’t just go on a whim, but really need to prepare and expect to deal with all sorts of challenges – sounds like my kind of trip!!
Yes, Kathi, same here. A lot to prepare beforehand and more challenges when you´re there. I love that kind of adventure, although I´m a bit scared already.
Thank you for sharing these helpful tips! Appreciate your work!
You´re very welcome, Shubhit! Thank you for stopping by!
Hello Pia,
wonderful post. I must prepare myself before Cuba, because I have a strong wish to visit Cuba.It seems it great country and people are very happy 🙂
Hi Ben, I hope it is like the people say. Cuba is a long time on my wishlist and now I have the opportunity! I hope you will have the chance, soon.
I was in Cuba last year and I loved it. Your article makes me want to return.
Hey Wendy, Thank you for hanging out here. If you like to go back, what about coming around in April? 😉
Both Cuba and Mexico are beautiful and diverse countries, I’m sure you’ll love it!
One other thing to keep in mind about Cuba is that it’s very hard to get cellphone signal or internet there. When I visited in 2016, only the very fancy hotels had wifi, and my whole group had no signal the entire week we were there. It can freak some people out, but it’s good to know ahead of time and be prepared!
Oh yes, that´s a great hint and of course, a point to consider, Nathalia! For me, it won´t be a huge problem to have some “off-time” but I understand that for other people it might be a bit scary to be completely cut-off from the world, having no internet and so on.
Love this! I have been considering Cuba for a yoga retreat in the future. I know there is a lot of research and paperwork to be done so this is very helpful.
Argentina, It´s my pleasure if I could help you. To put those things on a list feels a bit less overwhelming with all those things to think of. Feel free to get your travel checklist and print it out for one of your next travels.
Hey Pia,
I am so happy for you, that you will have the ability to work remotely! You can be proud, that you had the courage to ask your employer about it! Thank you for sharing this private fact. From a distance, it seems that it is for other people so easy to travel. But it is good to know, that other people have to figure it out, too. Holidays are not endless.
Thank you for sharing your travel tips. There are so many facts you have to think about it. I guess, sometimes it feels overwhelming. But it is so much fun, too. I am looking forward to reading your experiences!
I wish you good luck with your preparations!
Hi Breena, thank you for stopping by and leaving some nice words. You are sooo right. Some people think I have an endless amount of holidays until I explain how I put my vacation time together. Remote work, public holidays and a few overtime compensation. I am fortunate enough with my company and especially my boss, that those things are possible or can be made possible. But in the end, it is hard and good work only who allows me such “deals”. If I fail to work remotely, I am sure also my boss will say “no” the next time. So I have to be twice as excellent as I usually am. And I believe (and it was hard work for me, too, to set up this mindset in my head) that without asking, a lot of opportunities won´t be used. The worst thing which could happen is that you will get a “No”, right?
Your assumption regarding the travel planning process is also correct. Sometimes I feel a bit overwhelmed by all the single points. I almost forget how much it can be (sometimes also complicated) to prepare such a trip. Especially, such a huge trip. In the ned, it will be a kind of three trips in one vacation. And each of them has different requirements than the other. But it is so much fun and every time when I can tick off one point from my checklist, I am so excited. It´s crazy…
I guess this trip with working remotely is very important. Important for you to show, that you are able to work while traveling. And also that your boss seems that your work is great and you will be allowed to work remotely again. So this feels like a lot of pressure. But it is part of achieving your bigger goal, so it seems to be necessary. And of course it is a great challenge, isn´t it?
Like you know, I am planning my Africa trip. Right now I am thinking “Girl, why not just Tanzania?!” I knew I would not have much time at every destination – okay, I had no destinations planned. 😀 But yes, it is so hard to decide, where to stay longer and on the other hand, where to stay shorter. But it is also a great opportunity to have a glimpse into different cultures and to come back for a longer stay. So, I feel you. 🙂
Looking forward hearing from your adventures!!! <3
Yes, it is a lot of pressure but on the other side we (I) had tested at a few occasion and already proofed that it could work, but of course, not for such a long time.
That is why I love to be as flexible as possible and I don´t like to be part of a well planned but stick with a strict time schedule group travel thing. I understand that for a lot of people this is the most convenient way of traveling as they do not need to take care themselves of the various things. But for me, I love the freedom of deciding myself where and when to go. I also look forward to your adventures. Africa (except the northern countries, like Morocco etc.), in general, is a completely new territory for me. 🙂