So You Want to Go To Cuba


I’ve just returned from a weeklong trip to Cuba, where I celebrated my 30th birthday alongside of three of my best girlfriends. It was one of the most incredible trips I’ve ever taken, but it wasn’t the solo backpacking adventure I’d taken in my younger days.

I didn’t spend hours walking around in the heat to try to find the cheapest bed to sleep in. I didn’t bicker with my friends over how much dinner or lunch was going to cost.

Am I getting older in my travels? Or am I just getting smarter in the way I go about it? Either way, this trip was planned exactly as I wanted it to be—completely stress-free and awesome. I’m going to tell you how I did it, and how you can do it too.


Best trip EVER

Flying to Cuba

We flew in through Panama City on Copa Airlines from NYC. It was a pretty simple series of flights (and there’s free wifi in the Panama City airport). At the gate where we boarded our flight to Havana, we purchased a Tourist Visa card for $20.

Cuban immigration did not stamp our passports when we entered the country, and instead, stamped the tourist visa, which is just a piece of paper that they keep half of. For some reason I was nervous when going through customs in Cuba—I had no reason to be. It was super easy and quick!

Soon, Jetblue will be offering direct flights to Cuba. BUT, you’ll still need to qualify under one of the 12 categories and will have to declare which category when you board the plane from the USA.

The 12 Categories

You’ll need to fall into one of these categories. We checked journalism and had no issues.

The categories are:

1. Family visits
2. Official business of the U.S. government, foreign governments, and certain intergovernmental organizations
3. Journalistic activity
4. Professional research and professional meetings
5. Educational activities
6. Religious activities
7. Public performances, clinics, workshops, athletic and other competitions, and exhibitions
8. Support for the Cuban people
9. Humanitarian projects
10. Activities of private foundations or research or educational institutes
11. Exportation, importation, or transmission of information or information materials
12. Certain export transactions that may be considered for authorization under existing regulations and guidelines.

If you are a travel writer, you should be fine claiming journalist activity. No one really questioned us on who we write for or what we do upon our return, though we had assignment letters printed out that we carried with us just in case.

Returning Through US Customs

We were honest about traveling to Cuba and were not given any trouble by the immigration officer. We marked that our trip was for business and all he asked us was how we liked it–he wanted to know where to stay and what to see and was so curious about going! Don’t be nervous about customs–just be honest.

trinidad cave, cuba

I turned 30 in this nightclub, in a cave, with the best friends a girl could ask for.

Booking Casa Particulares and Hotels Online

Right, this is where things get tricky. I searched for hours and hours and couldn’t figure out how to book a hotel or a casa particulare (a room in a Cuban house, which is the best and most affordable way to stay here) online.

I don’t know if the infrastructure is just not there yet, or if it’s intentionally difficult to book things online as the internet costs $$ in Cuba, but we eventually just booked an Airbnb for the first night.

Scheduling the Old School Way

You won’t have service and you won’t have internet, which is what I loved most about my time in Cuba. So you will need to schedule things the old school way—coordinate a time and place to meet with your Airbnb host, or your tour guide, or your friends.

best tour guide in Cuba

This is Cristian, the best tour guide ever. He totally made our trip!

Hire a Tour Guide

Because it was my birthday trip and I am always the one planning travel, I just wanted to relax on this trip and not be the one responsible for everything. Luckily my friend Autumn connected me to Cristian before our trip—he was the most incredible guide!

I reached out to him roughly two weeks before we left, telling him I just wanted to be on a beach for my birthday, see some things and have fun. I left the itinerary and details all up to him, and he planned the most EPIC week for us. He booked our driver, our classic American car, all of our casa particulares in each city we went to, our itinerary, and was there for it all. Above all else, he was our friend. He took us out with him, he introduced us to his friends and family. We went dancing, we drank rum. We became such good friends and I love him dearly.

This trip would not have been the possible nor would it have been the same without him. If you shoot me an email (Kelly @ gogirlguides. Com) I will give you his email. He’s amazing. This is hands-down THE BEST way to plan a trip to Cuba.

You don’t need to book a super expensive people-to-people program. You just need to be connected to the right people who can help.

cuba tour guide

You can tell how close we all got– he snapped this selfie while we were all passed out! He looks like Cuban Fabio, we look awful. Our favorite pic of the trip!

The Wifi & Service
Yeah, there isn’t any. You can buy an internet card that will get you two hours of service in a wifi zone (usually a park or a hotel), but we heard that it was super slow so we all decided to take a week off and just enjoy the trip. What a joy it was to not be on our phones at dinner—we got back to what was really important: enjoying each other and this beautiful country.

The Electricity
You’ll find plugs like you’re used to in the USA all over the place, so you shouldn’t need an adapter. Most outlets are 220 volts so maybe leave your straightener at home. We decided to be super chill on this trip—no fancy hair tools, hardly any makeup. It was incredibly freeing.

Tipping is expected in Cuba, just like it is in the States. Tip your taxi drivers, your guide, your restaurant servers all 15-20%. Be a good person!


Our ride for the week. A 57 Chevy named El Bolo

This is another tricky part of Cuba. You will get penalized 10% when you change your money in USD, and your bank cards will not work so you need to budget to have enough cash because you can’t just hit the ATM when you get low.

We changed over our USD to Euros before we got to the country, which saved about $50 in fees. But, if you bring USD you can still change it. The rate is roughly 1 CUC to $1USD, but if you change over $60 for example, you’ll get roughly 45 CUC.

You won’t get a great rate at the airport. Instead, we asked our airport taxi driver to take us to a cadeca in the city where we changed our money for the week. We budgeted roughly $600 per person for the week. After paying the guide + driver, we all wished we had a little bit more. But if you’re traveling independently, this should be more than enough.

DO NOT CHANGE MONEY ON THE STREET. Tourists will undoubtedly use the CUC, not the CUP—and if you change your USD with a random person on the street you might end up with CUP that you’ll have a hard time spending.

What Things Cost

Meals: Budget to spend 10-15 CUC on meals. You can do this cheaper (we definitely found places where the meals were between 2-5 CUC and DELICIOUS) but Cristian took us to those places, and I’m not sure we would’ve found them otherwise. To be safe, this is a good budget. And factor in your tip!

Drinks: Rum is crazy cheap. An entire bottle cost us 4 CUC ($4), and your beers will cost you between 2-3 CUC also.

Nightlife: Most places have a cover. Our favorite place was the Fabrica de Arte, which had a cover of 2 CUC each night we went.

Guides + Drivers: Expect to pay roughly 50-100 CUC per day for a guide, and roughly 100-120 CUC per day for the driver. This will include gas, but it will not include tips. You will also need to pay for their meals when you’re traveling with them, so factor that into your budget!

Accommodation: Most casa particulares that we stayed in cost roughly 50 CUC per room. We stayed 2 to a room, so it was $25 per person, per room and included a delicious home-cooked breakfast (usually eggs, toast, coffee, fresh fruit and juice).


Our Itinerary

We didn’t have nearly enough time in Cuba. Is there such a thing?

We spent 3 nights in Havana, 1 night in Trinidad (which we LOVED and wish we could’ve seen more of) and 1 night in Varadero. Varadero had a lovely beach, but the town was so-so, and we probably wouldn’t go back.

Trinidad was a gorgeous old multi-colored city, home to a nightclub IN A CAVE (where I turned 30 at midnight) and a gorgeous waterfall a short drive away. We absolutely loved it and wish we could’ve stayed longer.

Hopefully this helps you plan out your Cuba trip a little better!

Have you been to Cuba? What was your experience like?


About Author

Kelly Lewis is the founder of Go! Girl Guides, the Women's Travel Fest and Damesly. She's an optimist, an adventurer, an author and works to help women travel the world.


  1. I’m going to compete in an athletic competition in the spring. I know I have a few down days so I might have to email you for a that guide’s info.

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