Featured, Interviews, Travel, Travel Tips

How to Experience Cuba Part 1: Plan Your Own Getaway

December 12, 2016

In case you haven’t heard, Cuba left the gate open, and now errrrrybody and their momma, and their homegirl’s 98 line sisters, and cousin Rae Rae ‘nem are all trying to get in. Now that it’s so much easier to visit, attractive deals are popping up all over the place. The airlines are totally on board, and some of these round-trip fares are so low I honestly thought it was a setup, and they’re actually flying us all back to Africa. #becauseTrump

But alas, the fares are real, and my DMs have been on fire with questions from everyone who has booked! So I spoke with some folks who’ve been recently to show how to experience Havana in 3 different ways: 1) Plan your own trip 2) Join a group or 3) Use a travel agent.

Since most of you are planning your own, I spoke with a friend who’s been twice and planned everything himself! Richard Cantave is a humanitarian, champion of Haiti, and amazing human with a huge heart for helping people. He’s visited 50 countries and counting, and whether it’s a mission trip or a getaway with friends, he’s been fortunate to see more of the world than many see in a lifetime!

Richard, between your full time job and all of your humanitarian work, you are always on a plane! What made you add Cuba on top of all these other trips?

Cuba has always been one of those places I’ve dreamed about. I’ve always wanted to “step back into time,” and see the beautiful old cars parading down the Malecon. Most importantly, being Haitian, it was almost a duty to pay our Cuban brothers a visit at home since Cuba has long been an important ally of Haiti, sending hundreds of doctors to Haiti to help throughout all the hardships we have endured. I owed it to the Cuban people as a token of appreciation. There was no other country I wanted to visit more than Cuba, and now that I did, I can’t stay away for too long as I’m getting ready for my 3rd trip there.

So you knew this question was coming (sorry). What’s up with the 12 travel categories? Do they hem you up like Debo at customs with some crazy pop quiz on your “Educational Activities”?

This is the question I got so tired of answering upon my return to NY after my first visit to Cuba. It seemed like no matter how much I would tell folks that this was just a protocol and it was not enforced, they continued asking over and over again. The 12 categories are part of an old-system established during the embargo which required US citizens to apply for a specific license to gain authorization to travel to Cuba. Since only Congress can lift the embargo, President Obama used his executive power to lift the “requirement” to apply for authorization, and left it as a self-certification process. Technically, under the law, you can only visit Cuba if your travels fall under one of these approved categories. However with President Obama’s method, it became easier for anyone to travel to Cuba as you are NOT asked any questions nor required to prove that your travel falls under these categories.

So I kinda ran out of money when I was there (Like all the way broke. I barely made it back! Read about my #budgetfail here]. How did you decide how much spending money to bring with you?

Well the funny thing is, a friend and I kind of “ran out of money” too 😀 !  But to first answer the question, I don’t drink so it’s usually easy to plan an average amount for meals/necessities for me. I heard/read so many people say to bring more than you would need, so I decided to bring more than what I normally spend on vacation – exchanging just some of it.

Our last night we made the mistake of taking a bicycle taxi without negotiating the price first, and upon arrival he demanded $25 CUC [$25 USD]. We only had $15 CUC left (aside from the USD I had upstairs locked in my luggage in case of emergency), it was nighttime, and we argued the amount with him for almost an hour. A short trip to a police officer in the streets of Havana resolved the issue, and we ended up giving him $20 CUC which was all we had. So it’s not so much what you normally spend, but you need to prepare for anything.

If someone only has a few days in Cuba, what are 3 must-do activities they have to experience?

I would highly recommend they do a classic car tour, which will highlight all the key sights of the city. Definitely pay a visit to Fabrica de Arte between Thursday and Sunday. If possible I highly recommend taking a day tour to Viñales, or with a little bit more time, try to visit Trinidad de Cuba which was my favorite part of Cuba. Casa de la Musica was amazing with nightly performances starting at 9:00pm and soon after ending the night at Club Ayala affectionately known as “Las Cuevas”–a modern nightclub deep in a cave.

Did you stay in a hotel or a home (Airbnb, Homeaway etc.)? Any recommendations on doing either?

I’ve always opted for Airbnb to get a full blown Cuban local experience. The homes are gorgeous, the people are friendly, their meals are delicious and it makes the experience even more authentic. I definitely recommend staying with a local Cuban family.

Did you feel Havana was safe enough for people (especially women) to just roll solo or with a friend?

I have traveled to more than 40 countries so far and not a single one (not even the U.S) has felt safer than Cuba. To describe how safe it felt there, I always say that you could probably walk down the streets of Havana with a bag full of money and no one will pay you no mind. I think Cuba is a destination for all types of travelers: solo, groups-regardless of gender.

Thanks so much Richard! If you want to see keep up with his travel adventures, follow @haitiannomad on Instagram.


If there’s no time in your schedule to plan your own trip, consider joining a group trip or working with a travel agent to do it all for you! See below for more info on both, plus some of my own tips.

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