Roulette Travel Guide: Getting to, thru (and outta) Cuba

For a long time, U.S. Citizens couldn’t go to Cuba due to the longstanding embargo until changes were made that finally opened travel again in 2014. I feel fortunate to have made it to Cuba before more changes to our country’s travel policy are made that undid the loosening of the restrictions. Recently, the administration removed the ability for US citizens to travel to Cuba by cruise ship, or under the ‘people to people’ visa, which were two popular ways to visit the island.

Enough about the politics though – well for now, we will discuss a little more about how you get to Cuba (or how we did at least) by applying for a visa ‘In Support of the Cuban people.’ The opportunity for this trip popped up when a friend (who I had recently met while working from a Starbucks, still in the corporate world at this point) got an alert for roughly $280 flights from Albany to Cuba, and well the rest is sort of history (I can rarely say no to a cheap flight).

Trip Overview

Duration4 Days/4 Nights
Flight (United)Albany > Newark > Havana
TransportationTaxis and Horse Carriage
AccommodationsAirBnB’s known as ‘Casa Particulares’ – private residences that are tailored and licensed by the government for tourist stays
FoodMost meals are $3-10, beer $1-2, cocktail $2-4
WeatherHot but breezy, light rain first day
ItineraryDay 1: Arrival and travel to Vinales
Day 2: Plantation tour and explore Vinales
Day 3: Travel to and explore Havana
Day 4: Havana and beach day
Day 5: Depart Havana Midday

The flight itself actually came to a not-as-cheap-as-I-thought $341 when accounting for the various Cuba taxes, fees and charge for the Cuban Visa. Speaking of that, there are 12 current ‘valid reasons’ for U.S. Citizens to travel to Cuba, and when you purchase your airline seat, the carrier should prompt you to note which reason you are traveling for. I’ll keep any political thoughts out of this, but this seems like unnecessary red tape, but hey, we still got to go.

Know Before You Go


The valid reasons for a US citizen to travel to Cuba, according to the U.S. Embassy, 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 informational materials
  12. Certain authorized export transactions

We went with the reason of support of the Cuban people with the airline, and prior to boarding our final leg to Havana, we were prompted to purchase our visas at a little kiosk by the gate. Pictured is the receipt from the visa, from ‘Cuba Travel Services, Inc.’ – I would be slightly curious to see the owner of that business.

After the trip, we saved our receipts as well as what we did (we had a pretty good log of photos) in case we were ever asked to provide it.

But, after nearly a year, I think its safe to say that we won’t need to send further documentation anywhere. According to the Department of the Treasury’s guidelines (which are fuzzy at best), this visa requires:

  • Each traveler utilizing this authorization engage in a full-time schedule of activities that enhance contact with the Cuban people, support civil society in Cuba, or promote the Cuban people’s independence from Cuban authorities and that result in meaningful interactions with individuals in Cuba.
  • The traveler’s schedule of activities must not include free time or recreation in excess of that consistent with a full-time schedule in Cuba.

So, basically we would – spend money on Cuban goods, services and food, be on good behavior, and not engage in a whole lot of free time, and interact with the locals in a meaningful way. Sounds a lot like tourism to me, but its not. Thats not allowed.

Cash and Currency

Oh – and speaking of spending money in Cuba. You actually won’t be able to use any credit or debit card that is linked to a US bank when traveling in Cuba. Also, there is an additional 10% fee if you try to change US currency for Cuban Pesos, so we took the advice from another traveler, and pooled our money together to be able to buy Euros from our local bank in the US at the going market rate. Then, when we got to Cuba, we exchanged these Euros for Cuban Convertible Pesos (CUC). You want to make sure to bring plenty of cash – as you will be smack outta luck if you come up empty a few days short of when you plan to leave.

Always make sure to double check your change though – as there are two types of currency – one is the CUC (the Cuban Convertible Peso ), and is pegged to the dollar, and the currency you will use during the trip there. The other currency is the CUP (Cuban Peso), and is worth 1/25 of the CUP. Make sure that you are never given CUP as change, because you will be getting seriously shortchanged. Luckily, this never happened to us, and we never felt like anyone was trying to swindle or play a trick.


One of the biggest questions that I was asked prior to visiting Cuba and after returning was “was it safe” And, for the most part, my answer was yes. Aside from the issue with our casa partiular (see final thoughts at the end of this blog), we had absolutely no issues in Cuba. Even in crowded city streets, lower income neighborhoods, and dark alleys in Vinales, we felt safe and secure. Some of that security comes from the Cuban people’s appreciation for the money that tourism brings in – and the fear that even just one incident could hurt future travel. As always, always be aware of where you are and your surroundings, but don’t stress too hard about it.

You don’t need to worry about carrying around large amounts of cash in Cuba either, despite it being well known that U.S. travelers will need to use cash for their entire trips. The Cuban people are extremely respectful of US tourists, and we even met many solo female travelers along the way. Exercise the same caution you would anywhere else, and utilize in room safes when possible. I brought the Euro equivalent of $500 for the four days – likely more than enough, but I didn’t want to be scrounging for cash (and sure enough, others in the group later were, and I offloaded the little extra that I had left over).

Another thing that is important to remember when visiting Cuba, is that it is still a communist state. The government does control a lot of the daily life, and there are mixed opinions among the Cuban people of the government’s effectiveness. While some despise the communism, others came from a time where violence and hunger were rampant – and so their situation is actually better now. As such, regardless of how you feel about it, I recomend keeping opinions to yourself and not probing too often – as there have been stories of tourists getting reported for sharing too much anti-communist sentiment. More on that later.


As a general rule, it is unsafe to drink the tap water in Cuba, and you should only drink bottled or filtered water. We did have drinks with ice in them, but some places boil their water prior to making ice, and we didn’t have any sickness – but you may want to be weary if you are going to be there longer.

As a rule of thumb too, in Cuba, sometimes shops can be fewer and farther between as soon as you get out of the popular city areas. When you see an opportunity to get a good amount of water, it makes sense to grab some extra. It can be very hot and humid in Cuba, and you don’t want to suffer from dehydration.

You can also avoid this by bringing along a filter – I brought the Sawyer Squeeze, and did filter a few bottles of tap water when we were running low in the AirBnB and didn’t want to run out. I never felt any sickness, and never tasted anything undesirable after filtering.


There is very little good wifi in Cuba – most of it is run publicly, as it is apparently censored. Walking through public areas, you will be able to see people crowded around areas with their phones out – signifying somewhere that gets public wifi. And – you have to pay for it.

Wifi Card or ‘Tarjeta de Wifi” for use of WiFi in public places

One hour of WiFi use goes for about $1-$2, depending on where you buy your card. Luckily, it is not consecutive, so you can log on and use a few minutes at a time. That’s a good thing, because you may very well get frustrated after trying to use it for only a few minutes – I often had issues connecting. Make sure to download your maps prior to visiting Cuba, and if you need Netflix to fall asleep, make sure to download a few episodes as well.

Packing List

As usual, I flew with no checked bag, and just a medium sized backpack (not my gigantic hiking one, since we wouldn’t really be hitting any trails on this trip), but I pretty much always bring my boots anywhere that isn’t just a city, and in addition to Havana, we were going to spend 2 nights in the countryside of Vinales (2 hours west of Havana).

BackpackOzark 40L
Clothes4 Active T Shirts
1 Casual Shirts
1 Tank
2 Pairs of Shorts
1 Button Down
1 Pair of Pants
Bathing Suit
Light Jacket
Camera GeariPhone Gimbal
GoPro (I no longer use)
FootwearHiking Boots
Nike Free Runs
Water Filter*Sawyer Squeeze

Whew, alright – finally, lets get to the actual trip.

Day 1- Arrival and Vinales

Our trip from Havana to Vinales

We arrived in Havana, and after moving through a rather strange customs process (an agent was taking down our names, occupation, reason for visiting, etc on a pad of notebook paper), we came out to the cab area and met up with our arranged ride out to our Casa Partiuclar in Vinales. Our host there had been kind enough to arrange the ride for us, for $25 each (it was about a 2 hour ride). The driver was even cool enough to let us puff on some of the Cuban Cohibas we had already bought from a registered vendor in the airport. We had likely paid a premium for buying in the airport, but honestly we didn’t mind (if I recall I think they were $5 or $6 each). We had also heard stories about cars breaking down regularly in Cuba – a byproduct of the embargo that meant very few new cars have made it into Cuba over the last 50 years.

I chatted with a restaurant owner who agreed to give a ride in Havana in his early 1980’s Russian made Lada sedan – no a/c, manual transmission, no working gauges, and 200,000+ miles. He said that re recently had purchased it after years of saving up – for around $20,000. Above is a fun little compilation of cars for sale on, a car sales site similar to autotrader. You can see their pictured cost in CUC (which is pegged to the dollar), but note that even though every listing says ‘2019’, the cars pictured actually vary wildly in age.

And the new cars that do make it into Cuba? They can be a little expensive. While the average monthly salary in Cuba is about $20 (another reason why tourism has become so lucrative and prices are still so cheap), getting a new ride in Cuba could set you back $250,000 – for example, according to the BBC, a Peugot 508, which usually goes for around $29,000, was found listed at over $260,000. Enough about that though – we’ll touch more on the other byproduct of this – frankenstein classic cars – later.

Our driver dropped us off at our Casa Particular (AirBnB) in Vinales, which turned out to be quite a nice place, although the neighborhood did appear a little rough at first glance. But that roughness quickly wore off once we saw the friendliness of the town. We ventured out and about, on the hunt for something to eat and a little relaxation after a day of travel. Our Casa Particular was just one street off of Calle 241 (the main street highlighted in yellow above). We popped into a few bars and finally chose a place to eat – and I think I spent around $10 on all of that – see below. Twenty CUC could make one feel like a rich man in Cuba.

We later found patio seats at Centro Cultural Polo Montañez, a place that made for a great night of live music and salsa dancing (which I am terrible at both before and after several mojitos). There was a whopping $1 cover to get into the club, and drinks were all $1-3 – again, Cuba is cheap. Definitely recomend ending one of your nights in Viñales here at the Centro Cultural – and if you’re lucky, one of the locals might ask you to salsa and teach you a thing or two. We didn’t make it in, but there is also the Municipal Museum and Casa de Caridad Botanical Gardens nearby that are highly recommended by other sources..

Day 2 – Exploring Viñales

Viñales Valley, with the Guaniguanico Mountains in the background

Vinales is in the Cuban Province of Pinar Del Rio in western Cuba. First inhabited by tribes of the Taíno (that later were also refuge to runaway slaves), it was later colonized by tobacco growers from the Canary islands, and finally established as a typical community in 1878. Outside of the usual findings on Main Street and its colonial single story buildings, it is a mostly agricultural area surrounded by the low mountains of the Cordillera Guaniguanico range. Even though the range only tops out at a little under 2,300 feet, they still tower over much of the surrounding Vinales Valley – which is a UNESCO World Heritage site, and a prime area for hiking, rock climbing, spelunking and more.

Our first trek of the day would be a horseback ride to a coffee and tobacco plantation in the valley – an important historical and economical part of Cuba. Our Casa Particular arranged for our tour, where we would get picked up by a horse drawn cart and taken to the start of the tour – but we later found out that we overpaid by about $20 per person compared to if we had booked for ourselves. Not a huge deal, but if you are planning on making a longer trip, make sure to shop around for tours or guides so that you don’t overpay. Even at $30 per person, we were still satisfied at the end of the day.

Plantation Tour

  • Transportation from Casa Particular
  • Horseback ride to and through plantation
  • Cigar rolling demonstration
  • Tour of Tobacco fields and processing
  • Tour of cave
  • Coffee processing demonstration
  • Coffee and rum tasting
  • Lunch (extra cost)
  • Cigars, rum and coffee for purchase

We chatted with the different farmhands, and learned some more of the history about the plantation. Miguel, the man pictured above, is a third generation farmer on the all organic plantation working alongside his father and grandfather. Also a school teacher, Miguel shared stories about himself and Cuba while turning tobacco leaves into hand rolled masterpieces. We also learned a little more about how the relationship that their plantation has with its government – while they do not pay for any of their raw materials, they are required to sell 90% of their tobacco crop to the government for use in the cigar factories in Havana. The remaining 10%, the family either keeps for themselves, or sell/barter locally.

After an incredible tour and view into farming economy of Cuba, we headed back to our Casa Particular to take a break for a bit before our private driver arrived to take us on another tour around Vinales.

The first stop the Cueva del Indio, a famous cave system that had been inhabited by ancient indigenous peoples, and rediscovered in 1920. We were lucky to be visiting on a somewhat rainy day, which kept the cave from getting too crowded, but others have reported longer wait times.

A river flows through the cave system, and because of that, you move through it on a one way boat ride that lets you out on the other side of the cave not too long from where you started. The guide will point out some of the rock formations during the tour, but you might need to think with an imagination similar to how the Greeks looked at a few stars and haphazardly picked out constellation names in order to really see them. We continued on to another nearby cave system that used to serve as a hideout for runaway slaves, but now doubles as musuem by day and nightclub venue by night. Interesting combo for sure.

We continued on, enjoying the conversation of our cab driver, who was a lifelong Cuba resident who had seen the changes occur throughout the country’s history over the last 50 years. It was interesting to hear his perspective, as he had a rather favorable outlook towards the current state of Cuba which showed us that a lot of people are very supportive of the communist system. Apparently violence and hunger were rampant in the rural areas prior to the communist revolution – so for many, a system with limited upward mobility but the security of food and shelter is welcomed. Its interesting to see it up close and personal after only having read about it in books or articles online – we were actually in a communist country.

Our final stop in for the day in Vinales was at the historical Mural de la Prehistoria – a giant painted mountainside in the Sierra de los Vinales. The mural supposedly depicts the artist’s (Leovigildo González Morillo) interpretation of history and evolution leading up to the time of humanity. While the mural has faced criticism for its budget, maintenance, and initial timeline (it took nearly five years to complete). Regardless, it was a cool stop along the tour – but if you’re visiting in the busier months, I recomend that you do as we did and view from afar rather than deal with the potential for crowds up close. If you do want to go all the way up, it costs $3 for entry and a drink, and there is a small caffe as well. From there we called it a day and headed back for some R&R before we would leave for Havana in the morning.

Day 3 – Back to Havana

While it was hard to leave Viñales without getting into the mountains for a real hike, it was time for us to trade the rolling countryside and for a city to wander through. This time we were taking a shuttle bus (or van or truck – you can never really be sure what to call some of these franken-cars) – and this was one of the few complaints about the trip. Our driver seemed to take nearly an hour to get us out of the city due to several other riders that were running late, and then he stopped separate times for a sandwich and then for directions. In hindsight, it was almost a little comical. And then we made him pull the bus over on the side of the highway, for well, you know.

Getting into the city though – this was one of the more memorable culture shocks that I had experienced in my recent travels. It was crazy to think of the stark contrast between here and home (the United States was just 90 miles away). While vibrant and lively, it also felt third worldish – there were a lot of unemployed, decaying buildings, and lack of technology throughout the city. However, despite the third world vibes, I still felt upper second world country safe. Our second Casa Particular was a colorful apartment within one of said decaying buildings – one of those hidden gem type of places. Again, at around $50/night for 4 people, it was a steal too. Unfortunately, I didn’t snap too many pictures while we were inside – but I’ll look for a link to the listing.

The one picture I snapped in our Casa Particular luckily gave an approximate location

We started wandering the streets, working our way way down to the waterfront and Habana Vieja (old Havana). There are two distinct areas of Havana, Old and Vedado – and Old Havana is typically what most people think of when they picture the city. That is where we would spend the majority of our time. Some spots that we hit on our self guided exploration:

  • El Malecón – a waterfront boulevard stretching for 5 miles from Havana Harbor to the Alemedes River
  • Museum of the Revolution – dedicated to the revolution in 1950’s and Cuba’s history thereafter, featuring real planes and tanks
  • Parque Central – a plaza and park featuring many prominent historical buildings and gardens
  • Castillo San Salvador de la Punta – an incomplete fortress dating back to the 1500’s designed to protect the entrance to Havana Bay
  • Plaza de Armas – the city’s oldest plaza, dating back to the 1520’s

Day 4 – Havana Beaches and Night Scene

We couldn’t go to Cuba without getting out on a a beach and into some of the most crystal clear blue water I have ever seen. The trip was a bit too short and fast paced to have time for SCUBA dive, but apparently there are some incredible diving opportunities around Havana. We easily grabbed a classic Cuban car cab – $25 each way (for all four of us) to go to Santa Maria Del Mar about 12 miles east of Havana. I geeked out on getting to ride in a classic Chevrolet, powered by a Toyota Diesel, with what appeared to be a euro style home air-conditioning unit working to keep the car cool. Cool indeed. Since Cubans cannot easily buy entire cars or new cars, a lot of drives source parts from all over the place to put together their rides.

Our driver let us out near the beach, and agreed to be back in a few hours for our return trip. It seemed to be a fairly non-tourist beach (or perhaps a popular vacation spot for locals), as we didn’t see many other tourists there on the beach. We were able to use the facilities at a nearby hotel, and then snag a quick sailing charter for a whopping $3 per person. We finished off the day with a late lunch at a beachside restaurant, and then caught our ride back to Havana to check out the city after dark.

We started out with sunset drinks at the iconic rooftop garden bar at Restaurante de Plaza de Armas. Ernest Hemingway stayed here in the 1930’s, and there are even some of his personal favorite dishes served on the menu alongside traditional Cuban food. Its one of the more distinguished spots in the area, and even with that, heavy double pours of Cuban rum were around $2.

Continuing on after drinks, we went through the Parque Central again and enjoyed seeing the streets light up at night, as well as the slightly enjoyable eeriness of some of the quieter streets. We stopped into a local Cuban Jazz Bar – La Zorra y el Cuervo (the Fox and the Raven). Cover was $10 per person, but included two decently poured drinks and a few hours of relaxing entertainment to finish up our trip. The rest of my group would stay on for a few more days in Cuba, while I would head back the next day.

Final Thoughts (and one little issue…)

So – there you have it – four days in Cuba on a relatively modest budget -which, as long as you don’t spring for fancy hotels, isn’t too difficult. While I didn’t go too far into the food on this post, its not hard to find great little hole in the wall places anywhere you go on the island. Remember though – everything is just pretty cheap there – we over ordered our first few meals not realizing that $3 can get you a full plate of food.

During the trip, we never felt unsafe or like anyone was attempting to swindle or pull one over on us – I actually felt safer there than I have in some U.S. cities. After only hearing about communism in books, it was…interesting to see it up close and see the effects that it can have on a country. In a way, the entire island felt like it was one big family there – everyone seemed to know each other. When our driver once stopped to ask a random passerby for directions, the passerby ended up joining us for the rest of the ride.

Now – on the flipside of that – we did run into something pretty sketchky a few days after we all returned. The first casa particular that we stayed in reached back out to me via instagram, to ask if we had done anything out of the ordinary during our trip – which I firmly and confidently answered no to. You can see the messages below that we received – and naturally I was a bit skeptical.

Apparently (or perhaps allegedly), two state officers showed up at our casa particular, looking for our group and asking questions about our purpose for the trip, our work back home, our relationships to each other, and more. According to our hosts, they seemed to be particularly focused on those in our group who spoke some Spanish – an oddity to say the least.

For the above reason – while I would love to go back again, I’m unsure of the real reasons for the inquiry or if it was some type of hoax. But honestly, I really don’t want to find out in a communist country.

And here’s the full video from the trip – all shot on my iPhone!

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