A solo trip and unique experience in Cuba

Today’s guest post is by Steve Roberts, who is a Culture with Travel correspondent based in New York City.

Update from Steve as of July 17, 17. President Trump announced on Friday, June 16, 2017, that he was going to make changes to travel to Cuba. While it remains to be seen what is actually put in writing and into law, it looks like it will affect your ability to go under the People to People provision. If you are already booked to go, you should be fine from what I’ve read. If you’re thinking of going, either book now and go within the next 30-60 days, or wait and see for a bit. While President Trump asked for a quick turnaround, it may take months or maybe years before anything is actually changed into law.

Has Cuba been on your list of “need-to-go” spots? Curious what 50 years without U.S. contact is like and the effects of communism on an isolated state? If so, the time to go to Cuba is now. And, yes as Americans, we can. There are caveats, but nothing you can’t handle. I will say if you’re looking for the next Caribbean island to hit, and expect each and every convenience, Cuba is not for you just yet.

However, if you are looking for a unique experience and the opportunity to see a place living in the early 60s while going through transition before your eyes (primarily in the hospitality space) then this is the place. I thought it was great and I already want to go back.

Here is how I went about booking a solo trip following the current guidelines and some pointers:

Plane Tickets

I chose JetBlue since they fly to Havana direct from JFK (Miami and LA, as well). You need to choose from the 12 categories that permit travel to Cuba. Most likely “People to People” (sometimes referred to as Educational) will be what you fall under. Of note, fellow bloggers, you are not a journalist, and real estate agents, you are not doing professional research. You are going “People to People” and you will need to sign an affidavit (online with JetBlue) confirming this to get your plane ticket. Print a hard copy of your ticket. At JFK, you cannot use the electronic kiosk for Cuba, and you need to go downstairs to get your boarding pass (and visa). In Cuba, they do not have electronic kiosks, they have lines (when I went, checking in and out went smoother than expected).

Medical Insurance

You need medical insurance to get into Cuba. With JetBlue, it was included in the price of the ticket. Print out a hard copy of it to have on hand just in case. Vaccines are not required. Check with the CDC to make sure there are no outbreaks or new requirements (you should do this every time you travel). Also, they don’t exactly have Duane Reades and CVS stores on every corner, so pack whatever prescription and over-the-counter medications you need and bring some extras.


A visa is required to enter and leave Cuba. You can get it at the airport ($50) or via Cuba Travel Services($110 includes processing and FedEx shipping). I used their services and they were very professional and efficient. However, I should have just got at JFK. At JFK via JetBlue, you get your visa where you get your boarding pass, thus getting it in advance was not necessary. I cannot speak for the process at other airports. The Visa is a single piece of card stock with two identical cards on it, one for entering and one for leaving. You cannot get out of Cuba without it. There used to be a 25 CUC fee, but it too, was in the price of my JetBlue plane ticket.

Entry Forms

You will need to fill out two forms to enter Cuba. One is a health document, the other is the standard customs card. If you are American, do not check “tourist” and instead check “other.” While you can travel under “People to People” guidelines, you still cannot go as a tourist. You’re currently required to keep records of what you did for five years. Write a blog.


accommodations in Cuba

Casa particulars are the way to go vs. hotels in Cuba. Hotels are overpriced, star rating are not US standards and known to frequently overbook. I used AirBnB for the first time, and it worked out great. They had plenty of of places to choose from. Plus since you’re going for a “People to People” experience, staying with a local is the ideal way to go. AirBNB had places that were single rooms in a home, an entire home, and some new B&B-like homes. You need to book your accommodations 4-6 weeks in advance, if you want to choose from a selection vs. what’s left.


US credit cards and ATM cards don’t work. Bring cash. You cannot get Cuban currency in advance. Expect a 45-minute wait at the cambio (money exchange). Of note, Cuba has two currencies. CUC’s(for tourists, the one case you are a tourist) have monuments. Pesos (for locals) have historical figures. You can only get CUCs at the exchange. Make sure they give you CUCs, and make sure when you get change, it’s always CUCs. A peso is only worth about 1/30th of a CUC.


Classic cars in Cuba

Taxis and your feet will be your best mode of transportation. There are community cabs that are generally old beat up American Classic cars where you can try to jump in for 1 CUC, but they are primarily for locals. Gov’t yellow cabs for tourists and they will hit you with the tourist rate (from the airport to Old Havana you should expect to pay 25-35 CUC). From Vedado to Old Havana, they state 10 CUC. Negotiate, I usually got them down to 8) and of course refurbished Classic American cars (rates vary). Additional options include their Cocotaxis (3 wheeled yellow coconut shaped vehicles) and Taxi-Bikes are all over Old Havana.

As for getting around the county, I’ve heard their train system is terrible. Renting cars is not advised since not only do you need to pay cash, but if they claim damages upon return, it’s cash and you have no legal recourse. Your best bet is hiring a driver or the Viazul bus service (it’s in Nuevo Vedado).

walking around Cuba

Hablas Español?

Keep in mind: most people don’t speak English, so work on your Spanish and download the off- line Google Translate guide. I found the locals to be friendly and generally helpful. An important thing to note, especially in Havana, you are dealing with well-educated people that are paid next to nothing a month. Be careful when discussing the cost of things. Your 15 CUC lobster might be a steal – it’s half their monthly pay. Also, be careful discussing politics, they can’t speak about their leaders the way we do. Respect that and take it seriously.


Wi-Fi is rare, so get used to living like it’s 1999. You will need to rely on paper maps and guide books to get around. Print them out in advance.

Should I get a tour guide?

visiting art galleries in Cuba

If you are not going with a group tour, I recommend you get a tour guide for at least some of your time there. I reached out to a Cuban local named Raiza, as a friend referred me. I requested a tour of Old Havana with someone who knew the art galleries and maybe some artists and spoke English. She arranged a tour guide (Nicolaus) who is a multilingual university professor who not only knew artists that he introduced me to, but was an accomplished professional artist himself. Also, he had a wealth of historical knowledge and on what is happening in Cuba today. Feel free to leave a message in the comments section, if you would like Raiza’s contact info.


I don’t know where the hell “tourists” are going that they complain about the food. I’m sure there is mediocre food, but that’s true of most places. I ate well and some places I literally stumbled upon. Don’t drink the tap water, but ice in drinks is fine. I avoided raw veggies with the exception of fresh mint in Mojitos. I ate fresh fruit like mango, pineapple, and bananas, every morning.

exploring in Cuba


If you decide to pick up some artwork while you are there, there is some great stuff. Make sure you get the proper documentation, or it could get confiscated. Get your rum or cigars (if you fancy) at the airport, unless you are looking for something particular. The airport has limited choices for food, so either bring a sandwich from your Casa Particular, or pack some Kind bars or the like.

Returning Home/U.S. Customs

When you get back to the U.S., you will hit an electronic kiosk requiring you to answer a number of questions, most as to the value of goods and their nature. Then, you will speak with a Customs official (as is standard for international flights) to check your passport and ask questions like…

  • Where did you come from? Cuba is your answer, it’s where you went and what’s on your ticket, customs form and likely stamped in your passport.
  • Why did you go? To experience the culture. Keep it short and sweet.
  • What did you bring back? Rum, cigars, and chocolate. All perfectly OK to bring back. (I believe the total max you can bring back is $800.00 a month). I was welcomed back and waived though.

Now that you know what and how to do…what are you waiting for?

Born in Brooklyn, raised on LI, schooled in Mass, Steve’s port of call is NYC. He enjoys global travel and blogging about travels, painting, and photographing beauty in its many forms. Steve is a bit of a Foodie and enjoys a drink or three on occasion. Steve is an expert on what, where, new and old to do and see in New York City. Check out his local blog via Hunter’s Hot & Hip NYC. Follow him on Twitter, Instagram, and read about his world travels via Hunter’s Travel Tales

[Have you been to Cuba or would you go? Ask Steve any questions in the comments, and share about your experience!]

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