Update 6-17-17. President Trump announced on Friday 6-16-17 that he was going to make changes to Travel to Cuba. While it remains to be seen what is actually put in writing and then into law it looks like it will affect your ability to go under the Peope 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 Trump asked for a quick turnaround, it may take months or maybe years before anything is actually changed into law. I’ll update as new info becomes available. 

Has Cuba been on your list of Need To Go spots? Curious what 50 years without US 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 your looking for a unique experience and the opportunity to see a place living in the 60’s 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. The following is how I went about booking a Solo trip following the current guidelines and some pointers. 

Plane Tickets, Medical Insurance and VISA’s. 

I choose 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, Real Estate Agents you are not doing professional research and if you’re looking for a husband or wife…it’s not a religious experience even if it felt like one at the time. You are going People to People and you will need to sign an affidavit (on line with JetBlue) confirming this to get your plane ticket. Print a hard copy of your ticket. In JFK you cannot use the electronic kiosk for Cuba, 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 I expected).

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 DReade’s and CVS stores on every corner so pack whatever prescription and over the counter meds you need and some extra’s. 

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, as it turned out going from JFK I should have just got it there). 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. Thus, put in somewhere safe and do not misplace, lose or forget where you put it…unless you want to extend your stay. There used to be a 25 CUC fee to exist, it too was in the price of my plane ticket. 

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

Accommodations, Money and Transport


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 a great selection 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 they have left.  

US credit cards and ATM cards don’t work. Bring cash. You cannot get Cuban currency in advance. Expect a 45 min and up 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 CUC’s at the exchange. Make sure they give you CUC’s and make sure when you get change it’s always CUCs. A peso is only worth about 1/30th of a CUC. 

Taxis and your feet will be your best mode of transport. There are community cabs that are generally old beat up American Classic cars where your can try to jump in for 1 CUC, but they are primarily for locals. Govt yellow cabs for Tourists and they will hit you with the tourist rate(from the airport to Old Havana you should expect to pay 25-35CUC depending on your Spanish. 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 Cocotaxi’s (3 wheeled yellow coconut shaped vehicles) and Taxi-Bikes are all over Old Havana. 


As for getting around the county their Train system is known to be terrible. Renting cars is not advised since not only do you need to pay cash, but if they claim damages upon return, its cash and you have no legal recourse. You’re best bet is hiring a driver or the Viazul bus service(its in Nuevo Vedado).

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 a 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.

If you are not going with a group tour get a tour guide for at least some of your time there. I reached out to a Cuban local a friend referred me to.  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  for me that was a University Professor who was multi-lingual (fluent in English)and not only knew Artists that he introduced me to but was an accomplished professional Artist himself. Also a wealth of Historical knowledge and on what is happening in Cuba today.  


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 tap water, but ice in drinks is fine. I avoided raw veggies with the exception of fresh mint in my mojitos. I ate fresh fruit from fruits with skins i.e. Mango, pineapple, banana, etc every morning. 

Returning Home 

If you decide to pick up some Artwork while you are there…and there is some great stuff. Make sure you get the proper documentation or it could get confiscated. Get your Rum at the airport, Cigars as well 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. 

When you get back to the states 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(standard returning from anywhere outside the country) to check your Passport and ask questions Iike…
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? 

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3 responses »

  1. jnkbrdg says:

    I look forward to going in July!

    Do you have the contact information for the locals who provided you with the tours? I like that you were able to meet artists.

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