I’ve heard Cuba referred to as “frozen in time,” with it’s classic cars and vintage style. It is the country known for producing the best cigars and rum in the world. Cuba is also the “forbidden fruit” for Americans—the place we aren’t supposed to be (and for a long time couldn’t be as tourists). But in visiting Havana, Cuba, I discovered that there is so much more to this incredible country than what you may have been told or read about someplace—the people, places, sounds, smells and tastes of Cuba will surely exceed your expectations. They certainly did mine. Let me tell you about it…
(So, honestly. Do you want to read about my nostalgia, or just get to the “need to know?” I won’t make you suffer; just scroll down for the Fred FAQ/things you will find helpful when visiting Cuba for the first time.)
I have to admit: my interest in Cuba was inspired by an early fascination with cigars. Initially, that was the whole basis for my curiosity about the country (Admittedly, I am somewhat ashamed I was that limited in my scope of the world at that time. A whole country. Cigars? Come on). My father smoked cigars from time to time when I was young, and I always thought they smelled incredible and that it was sophisticated and “mature” to drink a fine scotch, whiskey, rum or coffee and puff on a cigar. When I turned 18, he took me to buy some cigars of my own—no Cubans, of course, as they weren’t and aren’t available for sale in the US. From there my interest led me to a summer job in a cigar store in Scottsdale, AZ (Churchills Fine Cigars), and later one while in college in Dallas, TX (The Tobacco Gallery) where I learned many of the nuisances of the cigar aficionado. And all the while, the concept of actually visiting Cuba to experience the tobacco fields and see the cigars rolled seemed more than foreign. Because of international relations, based on 40-year-old “bad blood,” I believed it would always be impossible. But while working in the industry, that was almost all people talked about: the elusive Cuban cigar.
In the mid 2000’s I began hearing of Americans visiting Cuba. Most of the trips I was aware of were feigned “religious missions” or “humanitarian efforts.” That’s not to say people weren’t actually doing that, they just weren’t the people I knew. Other friends were flying to Canada or Mexico and connecting to Cuba through there, while not having their passports stamped. All of this seemed risky and distant to me, and I didn’t put much time or energy into actually formulating a plan to see Cuba for myself until a few weeks ago. President Obama seemingly opened the door for Americans in Cuba, and then President Trump’s policies have become more restrictive. So, what is the reality? Can we go? How do we get there? And, is it difficult, dangerous, or risky? The answer is YES, we CAN go (as of the writing of this blog), and in my experience, it was neither challenging nor prohibitive.
To formulate a plan to get to Cuba from Chicago, I made a simple Google search. It was something like “American travel to Cuba.” One of the first results was a link to the Cuba Travel Services website (https://www.cubatravelservices.com), a company for which I was entirely unfamiliar. I had no idea what the Cuba travel industry entailed, but, in all honesty, it was a very fortunate search for me, because these people are incredibly helpful and knowledgeable. While you CAN book your own travel to Cuba, there are a few things to consider (all of which CTS can assist with):
1) American credit cards are not accepted there (yet), so all transactions are in Cuban currency (“CUC,” cash). A Cuban licensed travel agency can book hotel, transportation, tours, etc., and you can buy them directly, using your card. CTS set up all of that and more for me and that significantly reduced the amount of cash I needed to bring.
2) An agency or advisor who knows Cuba can tell you exactly what to expect from accommodations. CTS provided me with a wide variety of options, from “AirBNB” “casa particular” style arrangements to 5-star hotels, and they got better than advertised rates. I showed up to my hotel with a pre-paid voucher, handed it to the reception desk, and I was done with check-in.
3) CTS works with specific guides. Large tour groups are available, but I preferred and was fortunate enough to arrange for a private, one-on-one local Cuban guide who was well connected around the city and had a vast, personal knowledge of all things Cuba. His perspective and relationships as a local proved invaluable. He arranged for airport transfers, a driver for each day or touring, restaurant recommendations, guidance on what to REALLY see, etc. Elio was TREMENDOUS, and I very highly recommend him and CTS.

4) They can book your airfare, but I did that myself on AA.com. Many domestic (US) airlines fly to Havana, and you can book on their website like any other flight.
Cuba Travel Services did inform me that I would need a visa to travel to Cuba. That seemed like a long process of approvals or extensive paperwork related matters, but it is NOT. I simply purchased a visa on their website and it arrived in a few days. I paid around $85 for the visa, and you can also buy them at the gate in the US before departure.
I do not claim to be an expert on the various classifications of travel to Cuba, but you will have to meet one of them to obtain a visa (https://www.cubatravelservices.com/faq/12-ofac-categories/). With the help of CTS, I chose “support for the Cuban people,” as my travel classification, and they helped me meet the requirements of that visa by arranging for a local guide, dining in local restaurants, etc.. I also met with CTS directly while in Havana to discuss using my platform to encourage further travel to Cuba (you’re looking at it), and did some investigation on ways I can assist with their animal overpopulation issue (that is a core passion of mine, and in future visits I am developing relationships to assist in their efforts by providing needed supplies.) But, full disclosure, I was never asked any questions about my purpose in Cuba by immigration or customs officials in Cuba or the US. I can’t promise that will be everyone’s experience, but it was mine and has been so for almost everyone I know who has visited Cuba.
Thanks to Kristen, Grace, Orieta, Ariel, Elio and everyone involved with Cuba Travel Services. I will be a customer each time I return to Cuba. I feel fortunate to have stumbled upon them, and I encourage everyone to take advantage of their expertise and connections. (They were also VERY patient, answering all of my questions, of which there were many).
Are you really reading all of this for my loquaciousness, or do you just want the photos and the tips? Well, HERE are my basic Cuba travel tips (and I will likely add to these as I recall them). More on the details of my stay and destinations I visited are below.
In all, I INSIST that you make time to visit this incredible country. The kindness, service mentality, optimism and hope of the Cuban people radiates through each human interaction I had in Cuba. I am grateful for the kindness they extended to me and for sharing the beauty of their city and country with me. Regardless of the number of times I will visit Havana and Cuba in the future (and there will be many more), this has been an adventure I will never forget.
Okay, the good stuff:
The FRED FAQ (stuff you should know if you want to visit Cuba, in my opinion):
• Call Cuba Travel Services (or another licensed expert), tell them what you want to do and let them know what kind of trip you’re looking for (sightseeing, historical, beaches, relaxation, traditional or luxury) and let them offer you a proposal. It will save you time, money and hassle.
(My room at Hotel Packard)


(The POOL at Hotel Packard!)


(The POOL at Hotel Packard!)


(On my last night at Hotel Packard, the maids left me this on my bed)
• I found that accommodations ranged vastly in price, style and luxury. I chose the BRAND new Hotel Packard (https://www.iberostar.com/en/hotels/havana/iberostar-grand-packard), and for some perspective, it was around $240 per night. It was also one of the nicest hotels I have ever stayed in, anywhere. A similar quality hotel in the US with the service and amenities would cost 3 or 4x MORE in the high season, I’m certain. Ask for my friends when you are there: Fidel, Miguel Angel, and Raul.
• On that note: Elio, my guide, told me that in Cuba one has to be flexible and have a plan A, B and C (sometimes even a plan A2, B2, etc.). Having a local contact will help with that. Things open and close at unscheduled hours, and like any other place, people can be undependable—the relationships and local knowledge of an expert went a LONG way for me in Cuba and I am certain helped me avoid frustration and hassle.

At first we couldn’t get in to this cigar rolling factory for some reason, but Elio worked his magic by speaking with people he knew. I saw quite a few people turned away from places because they didn’t follow the correct protocol for obtaining vouchers, etc.
• YES, solo travel is safe and enjoyable (I did it!)
• Cuba tourist currency is CUC (pronounced “cook”) and you can exchange the US dollar for it all over the place in Havana from the airport to hotels and even at some local businesses in the midst of a transaction. The current exchange rate is currently .87 to $1.00 USD. For the most part US credit cards won’t work in Cuba, so remember to bring enough cash. I am not used to budgeting my spending based on physical cash available, so that was a little unnerving, but it worked out just fine. The amount of money you need to bring is based on the same parameters you’d consider anywhere: what do you want to eat and drink and how much, how much do you want to shop, etc. For perspective, a mojito is 3-5CUC on average and a really nice dinner with appetizer, alcoholic beverage and coffee I found to be around 23CUC. I found tips to be included most places, but I included a little extra each time.

(As a tourist you want “pesos convertibles.” There is another, local form of currency that is best to avoid. Always make sure you are getting change in the correct form of currency)
• Meals are affordable, and the food is good. They serve beef, chicken, pork and vegetables. You’ll find rice with most meals (at least I did). I was told in advance not to expect much from the food, that it would be bland and uninspired. I found this entirely untrue, and in my four days, I did not have a single meal I didn’t find fresh and delicious. As for where I ate:
a. I ate breakfast at the hotel as it was included in my stay. It was a buffet, and it was extravagant and had so many different offerings, both with local and more traditional American breakfast fare. If you love coffee, drink coffee the way the Cubans do. It is strong, with a lot of sugar (to add, or already mixed in)
b. I had dinner at Habanera in Miramar with my new friend Ariel. The restaurant was a converted house and the food was incredible.
c. During my two tours I was taken to lunch. The first day at El Rum Rum de la Habana, and the second at Barbra Restaurante Bar. Both were private restaurants (private entrepreneurship is a new concept in Cuba). El Rum Rum was absolutely delicious and the service was outstanding. I highly recommend you take the time to check them out. Tell them I sent you, as the owners introduced themselves to me and were so friendly and accommodating.
d. A restaurant I kept hearing about but unfortunately did not book in advance was La Guarida (http://www.laguarida.com/en/). Apparently, it is a “must experience,” and I will be there when I return in January (yea, I am already planning a trip back!)
I never take pictures of my food, but this was from El Rum Rum
I never take pictures of my food, but this was from El Rum Rum
• While my hotel had filtered water, I avoided tap water for drinking and stuck to bottled water. It is everywhere, and I didn’t have any issues whatsoever. It is okay to drink beverages with ice.
• Internet in Havana is limited. Hotels will have it and there are some hotspots (while I never found one). You purchase internet cards (I got mine at the hotel) which provide a code to enter for a block of internet time (my cards were 5hrs a piece, but some places even a single hour can be 12CUC). Keep in mind that you will likely not be able to use your phone for navigation, so getting around Havana by foot can be a little tricky, and there won’t be the opportunity to search anything online of which you’re unsure or curious about in the way we do in the US.
• If you want to ride around in a classic pink Chevy (they utilize their beautiful classic cars as taxis), email Luis: elluisi@nauta.cu

• I couldn’t find a consistent answer on what I could and could not bring back from my trip to Cuba. The US embargo has made finding Cuban goods in the US impossible (and the sale of them is illegal). I brought back some rum and cigars in limited quantity and didn’t have any issue. That is certainly not legal advice from me, but I think in moderation and within the confines of the law and common sense it should be fine.
• DO enjoy the rum and cigars while in Cuba. The Havana Club rum offerings and Cohiba cigars (for example) we buy in the states are NOT the same thing, and you’ll immediately taste the difference.

• OH, and this note: As an American I was told to tell people I was Canadian when asked in Cuba. I was quickly informed by locals this was not only unnecessary but ridiculous. I did not encounter a single unkind Cuban during my time there. Sure, there is the occasional language barrier or shyness, but that is not to be mistaken with disinterest or dismay. I found the Cuban people to be warm, kind and proud. I also found this generation of Cubans to be grateful for our (American) interest in their country and appreciative of our generosity. So, when you visit, BE grateful of their hospitality, and as generous as you can be. One will be amazed at the excess we as Americans, even at the most fundamental level, possess and experience in comparison.
• As for what to see: There are countless landmarks throughout Havana to experience (Malecon, Morro Castle, El Capitolio, Museum of the Revolution, Bodeguita del Medio, Gran Teatro de La Habana, Havana Cathedral, Jose Marti Memorial, John Lennon Park, The Bacardi Building *former, Plaza de la Revolucion, just to name a few). Old Havana is a MUST, of course. La Universidad is beautiful. Make time to visit the tobacco factories (there are 40+, with a couple right in Havana). You can visit the longest cigar in the WORLD, rolled by Jose Castelar Cairo (who I met) and on display at La Triada Shop (photos in my gallery). And an unexpected but incredible stop was at “Fusterlandia,” an entire neighborhood inspired by a Cuban artist named Jose Fuster who himself was inspired by Gaudi’s public works in Barcelona (photos in the gallery, as well).


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