How I Spent 5 Days in Cuba

Although tensions between the U.S. and Cuba have eased within the last year, Americans still must navigate travel in the grey areas of our government rules until Congress lifts the US embargo on Cuba.

As I write this, U.S. citizens can only travel to Cuba if they are eligible for one of the 12 licenses now offered under the Treasury Department’s new rules. I’m a rebel and a risk-taker, so I check-boxed my reason for travel under “journalistic activities” and packed a couple of cameras and film without applying for a license. It’s actually not illegal to travel there — it’s just illegal to spend money there due to the existing trade embargo.

Flights: It was super easy to book my Cuban flight. My gateway city of choice was Cancun, Mexico and I booked online at Cubana Airlines. You’ll land on their website in Spanish, but just translate the site or choose English. It’s safe and legit. With an easy and affordable two hour flight from DFW to Cancun, Cuba is only another hour and a half away. You can also get there from Miami, Mexico, Canada, and the Caribbean (the closest gateway cities and countries to the USA). Other airlines that fly to Cuba from other countries include Copa Airlines, Cayman Airways, and Bahamas Air just to name a few. I’ve heard that custom officials in Mexico ask less questions than those in Miami — I’m not sure if I ever want to test that theory, but I definitely made it back in the States with no problems via Mexico.

Accommodations: Booking accommodations took a little more work. If you research and find something at least 6 weeks ahead of your trip, you should have no problem finding plenty of hotels. Unfortunately, I only had a couple of weeks to book something so my top picks like the Parque Central and Hotel Saratoga were already full. I booked my first night in Havana at the original Hilton of Cuba and former HQ of Fidel Castro, now called Hotel Tryp Habana Libre. The next two nights would be at the all-inclusive (my first ever type of hotel) Melia Varadero. My last night back in Havana would be booked at an Airbnb. Yes, there are plenty of “casa particulars” (aka budget bed and breakfast accommodations in a local’s home) which are sprouting up on Airbnb and they’re all quite safe and secure. will give you the current daily exchange rate (Compra means to “buy” and Venta means to “sell”)

Currency: One very important thing that you must be prepared for is how much you want to bring / spend in Cuba because no store or vendor will take your U.S. dollar bills or U.S. issued credit cards. ATM’s won’t work with your bank cards, either. You will be able to exchange your American money for Cuban money at a Cadeca (currency exchange location mostly found in Cuban airports and high traffic tourist spots), but even though your currency converter says that $1 USD = $1 CUC, the rate is actually less in favor for you and on top of that there’s an additional 10% tax for USD currency. So basically for $575 USD, I got $501 CUC back. Don’t get stuck in Cuba with no money! Make sure you cover for incidentals.

Language: It’s a no-brainer that Spanish is the official language of Cuba, and not many actually speak English — especially the older generations. So it’s a good idea to brush up, practice on Duolingo, and listen to some audio books just to get by with the basics. If you just try to speak their native language (no matter how bad you may sound) the Cubans will instantly warm up to you and go out of their way to help you. You’ll find more English speaking Cubans in the touristy parts of Havana and Varadero, and the locals who work in the tourism industry will speak English, obviously.

Day 1: Cancun to Havana

The first morning of my trip starts off muggy and hazy. The Cancun airport seemed busy for a Thursday. It was relatively easy to find the $25 USD Cuba tourist card visa which you can buy at the Cubana Airlines kiosk. It took me about 1–2 hours to just get through the check-in line and there is no 24 hour electronic check-in prior to your flight. Getting through security was much faster.

Once you get through to the departure gates, it becomes more bearable. There’s plenty of duty free shops and restaurants you can choose from. The gate terminal is sweltering — I’m fanning myself with my passport and boarding pass. There is no organization when boarding — it’s a free for all.

We take off on time and as we approach Havana it becomes ominously dark and rainy. The announcement is made that we’ve begun our descent, but then the flight attendant says we will have to reroute away from José Martí International Airport to Juan Gualberto Gómez Airport in Varadero instead because of bad weather. Varadero is a 2 hour drive east from Havana. We are then asked to deplane and sit tight inside indefinitely until the rain subsides and the Havana airport reopens. As we walked the bridge, the rain didn’t seem that bad outside.

Stuck at the Varadero airport

Sitting in the Varadero airport waiting for our flight to resume to Havana, I find it amusing and ironic because I’m scheduled to be in Varadero tomorrow anyways. It would cost me $135 USD for a taxi from Havana to Varadero. I really didn’t feel like paying that right now to get to my original destination and then have to turn around again tomorrow. So instead I exchanged some USD’s and sat around some more.

Cadeca: white stands where you can exchange your money for CUC’s

My seat mates and I get to know each other over the next few hours — they’re a lovely Australian couple touring North America. We share travel stories. The guy in first class in front of me is from South Dakota and dumb as bricks, but a sweet guy nonetheless. He tried to wing Cuba from Mexico and so far has learned the hard way that it probably wasn’t a good idea to not plan ahead. At least book your first night somewhere in advance, dude.

Cuban money and Cuban pizza at the airport

I go to the little airport cafe and have sausage pizza and a cappuccino for dinner — my first meal in Cuba. For some reason, I rushed myself through the meal and came around the corner to find my plane neighbors making a bee line to gate 5. They didn’t make any airport announcements — at least not audibly loud enough to hear from the cafe. I could have missed my flight, damn it! Three hours later of not knowing any updates or resolutions, we’re back on our plane.

About half an hour of idle sitting, the captain finally gets on the speaker and tells us that nine of the original passengers decided to stay in Varadero. So that means they have to sift through every one’s luggage to pull out those nine assholes’ bags. My 5:00pm Havana arrival time turns into a 10:30pm arrival time. I’m really feeling grateful that I paid extra online ahead of time for a late checkout the next day at the Hotel Tryp Habana Libre. I made friends with a local driver at the airport who would have been the equivalent of an exceptional Uber driver back home, and we refreshed each other’s Spanish and English as he drove me to my hotel.

The Hotel Tryp Habana Libre interior
Standard double room at the Hotel Tryp Habana Libre

I finally arrive at Tryp Havana Libre around 11:00pm and check in my huge, but dated hotel room. I asked for the ocean view, and the balcony was enjoyable from what I could see in the dark. It is true what they say in the reviews about the hotel’s elevators — you could be waiting 5–10 minutes just to get on one depending on the traffic of people and time of day. If you have a lower floor, just take the stairs. There’s a 24 hour cafe on the first floor where I enjoyed a tiramisu late night snack. I hit the bed by midnight and hoped for a better day tomorrow.

Day 2: Havana to Varadero

I tried to sleep in after my first rough travel day in Cuba but eventually got up at 9am so I wouldn’t miss out on the free breakfast buffet. My first view of Cuba in daylight that morning after the storm was a beautiful sight.

Oh Havana!

The buffet at Tryp was generous and a fiery red-haired older woman performed classic songs like “As Time Goes By” on an out-of-tune white piano which felt most appropriate. By the way, everyone smokes — its allowed everywhere! In hotels, bars, even airports… you can smell old, stale cigarette and cigar smoke in everything.

Traditional Cuban breakfast items

I had a cab drop me off at a Cadeca in Habana Vieja (Old Havana) near the Obispo and Aguiar calles (popular streets) so that I could get more cash. The USD exchange rates at the Cadecas were less expensive than the rate offered inside the Tryp Habana Libre hotel (note: most 4–5 star hotels in Cuba will offer to exchange your money but their rates are much higher than anywhere else). After getting my CUC’s, I explored the streets and sat down at a cafe for some coffee and live music. A weird Italian guy in the cafe insisted on taking pictures of me — maybe he thought I was Lucy Liu or something. I was called “china” a lot in the streets (“china” in Spanish means Chinese). Walking along the alleyways, I also noticed long lines of Cubans at the telecommunication stores that day and wondered if there was a new phone released or something.

Cuba coco taxis and pedicabs
Really good live Cuban music!
Handmade art in a local market
Parque Centrale
The hop-on-hop-off Habana bus tour historic route map

After further exploration I came upon Parque Centrale and found the hop-on-hop-off double decker Havana tour bus which I rode on for an hour around the historic neighborhoods. I’m starting to think it’s a good idea to pay for the hop-on-hop-off tour buses in every country I visit — its cheap, convenient, and you just get to see so much of a location in a shorter amount of time. $5 CUC’s was totally worth it. It was pretty interesting to see the different pockets of neighborhoods, historic architectural landmarks (like Christopher Colombus’ cemetery and the famous Che art piece on the side of a building), and people taking siestas in their cars along the streets. The seaside breeze and smells from the upper deck made it all more wonderful.

Ministry Of The Interior Building with the face of Che Guevara
State of despair and repair was a current theme in Habana Vieja

Feeling short on time for photographs, I hopped off the tour bus at my hotel and walked along the Malecon (the famous seawall off the Cuban coast) with my Mamiya 645 medium format camera. Along the way, I ran into a pedicab driver who let me take his picture and introduced me to his father who collected and sold antique cameras.

Eduardo, the pedicab taxi driver and his friend

He led me to his house and showed me his camera collection in his bedroom. It was surreal to be in a stranger’s home in a foreign country, sitting in a family’s living room where we only communicated in Spanish — his wife and child didn’t know English either. He tried to sell me a rare polaroid camera (the white one with the rainbow stripe down the middle) for $60 CUC, but that was too high in my mind and I politely refused. He also showed me other types of antiques from different countries — apparently he was a collector of all sorts and didn’t mind making a buck whenever.

Inside Eduardo’s house
Vintage cameras from who knows where

I thanked the family for their hospitality and offered $5 for their time (probably from the guilt that I didn’t buy any of their junk) and continued on my journey. On the way, a local Havana girl on the Malecon let me take her picture. This is probably my favorite photo from the whole trip.

It’s now about 3pm and I come across the famous and historic National Hotel de Cuba on the way back to my hotel. It was very nice as expected, but also a bit hoitty toitty. I sat for a few outside in the courtyard facing the sea.

The courtyard of the National Hotel of Cuba where you should have a drink and a cigar

Near my hotel I have some helado and coffee before I headed out to Varadero via a $135 taxi ride (I find out the following day that I was a dumbass to pay that much). There are lots of hitchhikers along the way to Varadero. I counted at least 50. The taxi cab driver gets a bit lost towards the end and complains that he’s been up since 6am. I give him a $5 tip out of sympathy and check in my very first 5 star all inclusive resort, the Melia Varadero. I’m starving so I immediately hit the buffet and pig out. It’s just ok, but not 5 star quality food. I was hoping to check the beach at night, but it had been raining since I arrived in Cuba. I didn’t find a hot tub so I just took a long shower instead and called it a night around 10:30pm.

Melia Varadero buffet

Day 3: Mantanzas

The beach at the Melia Varadero resort

Cuba is still grey and drizzly. The weather is starting to bring me down. I was hoping to get some sun time in at the beach, but there hasn’t been any trace of rays in three days. I’m regretting the fact that I booked two nights out in Varadero, in the middle of nowhere, with a bunch of honeymooners and old couples at this all inclusive resort when one night could have been enough. A bit bummed, I decide to book a half day tour to the Cuevas de Bellamar (Beautiful Sea Cave in Mantanzas) to take some pictures and avoid getting bored and feeling like I’m wasting precious time in Cuba.

I learned a lot from our nice and knowledgable tour guide. First of all, today (May 1) is Cuba’s Labor Day so most of the general public celebrated a holiday (except for those in the tourism trade, of course). As we drove into Mantanzas there were at least 500 locals all gathered in a park with a swimming pool bbq’ing and enjoying their day off. Varadero is also apparently not a true part of Cuba — it’s a peninsula that was made solely for tourists. Out of 3M tourists who visit Cuba each year, 2M of them come to Varadero. That’s why there are 57 resorts on this 1.2 mile peninsula stretch and 60% of the province residents work in tourism to have a better life. Many tourists don’t know the real Cuba outside of Havana and Varadero and surely not many know or visit Mantanzas. I also learned that the torrential rainstorm that delayed my flight into Havana the night before caused at least three casualties and heavy damage to city buildings in Havana. It was not a common weather phenomenon for the country as I originally thought.

Classic cars in Mantanzas
Inside the Cuevas de Bellamar

The Cuevas de Bellamar was first discovered in 1861 by a Chinese man who accidentally stumbled upon it. The little town where it resides is called Mantanzas, which translates to “massacre” where there is history of indigenous and Spanish bloodshed. The caves were interesting and our 25 year old tour guide developed a quick crush on me. I could tell because he was less focused on giving us an English tour and more so on getting my email and relationship status. After leaving the caves the sun finally decided to make an appearance and we take a quick walk around downtown and visited a local artist’s studio, the local bakery, and pharmaceutical museum. We close the tour with virgin cocktails at a bar that Hemingway apparently visited one night and make the trip back to Varadero.

Our lovely tour guide Oda showing us a propaganda poster of a extreme, local religion in Cuba
A local grocery store in Mantanzas
I met Billy from Toronto on the tour — he has been to Cuba 6 times
We visited an artist’s studio (pictured in the center) where he had works of art for sale
The local bakery — every citizen receives one free loaf of bread each and every day
The historic Museo Farmaceutico in Mantanzas
Old drugs from all over the world
Local Mantanzas men

A side note: most of “real” Cuba has no electricity — if the residents do have a bit of access, it’s usually only one bulb inside the heart of the house. Most buildings are dilapidated and non-air conditioned. People sleep with windows open covered by iron bars and use a bucket of water when they want to “flush” the toilets. Considering there are tourists (like me) who complain about Cuba’s “5 star” hotels, airports, slow service, and whatever else, I thought it was important to say that we can be a bunch of spoiled jerks who can be cheap when it comes to tipping and oblivious to the human condition of third world countries. Many Cubans I come across are surprised to find that I try to speak a little Spanish (from what I remember from my 6 years of learning the language), and instantly warm up to a genuine smile and salutation. They’re generally a happy people and are very proud of their wonderful and historic country. Cubans work hard and value family, love, fun and life just like the rest of us. So do yourself a favor and see the real side of Cuba outside of the tourist areas if you ever venture out here.

I arrive back to my hotel just in time to catch the last 30 minutes of warm rays on the sand before making my 6:30pm reservation at the Japanese restaurant inside my hotel. After the main course and right before dessert, I had to get up from my table and go outside to take pictures of the first sunset I’ve seen in Cuba. It did not disappoint and turns out to be one of the most beautiful spectacular ones I’ve seen in years.

After dinner, I give in and decide to pay $5 for 15 minutes of wifi to check in with my parents, my friend who’s sitting Pixel, and any important emails I may have missed. It turns out Airbnb reached out asking for digital proof of my passport since I made a booking in Cuba and I had to respond within 24 hours with a copy of it or they would cancel my reservation. Good thing I didn’t last long on the idea of “disconnecting” while I was here and good thing Airbnb decides to email me at the last minute about their verification process in a country where wifi is sparse and expensive.

Day 4: Back to Havana

Waking up early in the morning, I grab some breakfast and another 15 minutes of wifi to reply to Airbnb’s email (and chew them out for inconveniencing me) as well as confirm my arrival with my Havana host. I also shoot my Cancun host a little note on my arrival for the next day in case wifi would be hard to find again. I play it smarter this time around and reserve a group transfer bus in the afternoon to Havana for $25 CUC instead of the private transfer taxi rate at $135.

The sun is out this morning, so I grab some early rays at the beach before checking out. They’re celebrating “Cuban Day” today at the Melia Varadero hotel with live music, entertainment, and authentic Cuban food! I had seafood paella, potatoes, black beans and rice, a variety of grilled sausages, pork, corn and fresh sugar cane juice.

The sugar cane juicing machine they used at the resort (Funny or offensive? You decide.)
Live entertainers putting on a comedy show

Hammocks are strewn all along the beach, and I take a quick nap in one before heading to the lobby to catch my transfer bus back to Havana. I find out that the Solways tour guide wrote my transfer pick up time wrong on my receipt — he put down 1:50pm when the bus already came looking for me and left at 1:30pm! Thankfully they called the bus back to come get me — I almost missed my two hour ride back to the city! The transfer bus that picked me up is run by Trans Gaviota, air-conditioned and only $25 CUC between Havana and Varadero. I recommend this transfer service over Viazul (a public bus transportation system) not only because it carries a smaller group, but also because of the fact that they drop you off at your hotel as opposed to the bus station.

Part of a Cuban suburbia on the way out of Varadero

I found my Airbnb relatively easy from the dropoff at the Parque Nationale Hotel — it was about a 15 minute walk along the streets of Havana Vieja. After checking in with the young and well spoken host, I hop into a waffle and crepe shop called “Wanda’s Waffles” along a plaza and enjoyed a cappuccino and crepe. I overhear the cook and a gentleman at the bar speaking fluent English, so I asked them where they were from. It turns out they are brothers from Toronto and one had been living in Cuba and opened up this waffle and crepe shop. When I asked the pair where I could find some good cigars at a good price, Sam (one of the brothers) offered me a couple of celemone cigars (they’re apparently rolled by a guy who gets flown around the world to do this particular job) and introduced me to an art gallery where I found some great 80's film posters printed by the famous Cuban artist Eduardo Muñoz Bachs.

One of Eduardo Muñoz Bachs’ poster I purchased
#1 view of Havana Vieja from my Airbnb
#2 view of Havana Vieja from my Airbnb
#3 view of Havana Vieja from my Airbnb
Local fortune teller at the Plaza de Armes

I head back to my Airbnb around dinner time after saying goodbye to my new Canadian friends, and run into my host Tomas leading the other Airbnb guests / American girls from California into another casa particular because of the running water shortage (the detrimental storm and construction conditions affected the water system). Cool — I have the whole house to myself with the great view! We chat for a few and go to dinner together at a restaurant called NAO.

The last sunset I would see in Cuba

Turns out Tomas is a senior front end developer (probably only 1 out of 100 in all of Cuba) who also works for a mobile game startup! We have a great time talking about travels, friends, and startup life. It was a pleasant surprise to find such a young, tech savvy entrepreneur in a developing country. He even had a space invader tattoo on his leg.

Tomas walks me back to the house and shows me the Plaza de Armes and the famous bar where Hemingway supposedly drank himself drunk daily. He also tells me that since his father works for the government, he only makes $20 CUC a month. Our dinner tonight was $30 CUC per person. I can’t even imagine. That’s part of the reason why his family invests in property and rents them out to tourists like me. He said a small group from Airbnb HQ came down to Cuba to find casa particulars to join their program, while screening the area and neighborhood people. They found him and his family-run tour company called Since Cubans can’t have bank accounts, credit cards, etc. (they pay everything in cash), he has to use a work around where he ties in a PayPal account with his sister’s UK bank account. Of course Airbnb, Paypal, and the government take out their share of the pie before Tomas and his family can keep the earnings. I advised him to raise his rate since American tourism is about to burst the scene in Cuba.

A blurry Tomas and I at NAO
Hemingway’s bar
Plaza de Armes

We say goodnight and I write down the events of the day before heading to bed. Tomorrow I wake up early at 9am to head to the airport for my flight back to Cancun.

Day 5: Havana to Cancun

I wake up to take a shower with three buckets Tomas provided the night before. It wasn’t too bad pouring cool water over my head in the tub — I remember doing something similar about 20 years ago in Korea… The maid (who doesn’t speak a lick of English) shows up soon after and asks to use the phone. After talking with Melvis (Tomas’ mother), she offers to make me coffee. We sit down and chat for a bit in Spanish before Tomas shows up. Somehow we communicated just fine and talked about families (she had her first son at age 17), relationships, and work. She’s 57 but looks 40. She compliments me and says I look 25 after I tell her my age. She also feels compelled to tell me that there are good men out there in the world after I tell her I’ve never been married and have no children. She was super sweet.

My morning shower
The interior of my Airbnb
Local street artist drawing Che
Plaza de Armes
Last day in Havana Vieja

The day before, a different maid stopped by to leave a vacuum cleaner. The family must do well if they have two maids. Tomas arrives and shows me the cigars his friend got from the factory (Cohibas and Monte Cristos) and sells me a dozen of each for $65 CUC. I have a feeling I just bought a bunch of banana leaves, but if they end up being fakes, I’m ok parting with my money as a donation to Cuba.

His friends come pick me up and take me to the airport. The line to check in at Cubana Airlines takes another hour to get through. Other than buying a couple of souvenirs, I didn’t end up spending the rest of my CUC’s because there was nothing else to spend it on. I didn’t exchange it either— just kept the remaining $60 CUC’s for a future trip. I find the legit Cuban Cohiba and Monte Cristo cigars selling at $130 CUC a box of 25 or more at the airport. What a rip off. My flight is delayed an hour, and we finally depart around 3pm. I arrive at the Cancun airport two hours later and find my Airbnb host.


5 days is not enough time to experience Cuba, even for a first time visit. I recommend staying at least a week and spend your time in other cities besides Havana and Varadero. I heard Trinidad, Santiago de Cuba, and the Cayo islands were not to be missed and I plan to check them out on my next trip in the near future. Learn and practice a little Spanish before you come and book everything you want to see / do / try / stay in advance because they fill up quick! Once you get through customs in Cuba they will ask if you want your passport stamped. I declined since technically Americans are still under the embargo as I write this and I didn’t want to get in potential trouble, but by the time you read this things may be different.

You’re going to have to be patient with the airlines that fly in and out of Cuba. Leave your American expectations in the U.S. — your flight will probably be delayed and the whole check-in / boarding / status / process can be disorganized, time consuming, and frustrating. Just remember you’re working with an undeveloped country and their systems are not refined and efficient compared to first world standards. Also, be happy that you’re going to freaking CUBA! Relax and enjoy all the aspects of the journey.

Speaking of undeveloped, don’t expect to have wifi or cellular service handy unless you’re willing to shell out some cash. Cuba’s internet speeds are no where nearly as fast as the U.S., but if you need to send an email or text it will get the job done. Most hotels will have wifi access, but most casa particulars and Airbnb homes will have none. I highly recommend staying off the grid though — it was really interesting and freeing to not be so connected with the world back home. I enjoyed using physical maps, asking people directions and having conversations, and not being distracted by the need to look at my device constantly. It also adds to the appeal of being in Cuba — you’re in a different time capsule. Take it slow and just be “present.”

Other things I wanted to experience but couldn’t because of time constrictions were the Tropicana, the cigar factory / plantation tours, salsa dance lessons, and renting a classic Cadillac to drive around. Cuba is spread out so keep in mind transportation, travel time, and the self proclaimed local motto “5 minutes is 30 in Cuban time”. Cuba is safe, energetic and wonderfully rich in history and culture. Explore and enjoy it now before it loses its original charm and authenticity to commercialization and the tourism boom of the 21st century. I’ll definitely be back sooner than later!



Marketing Director, photographer, world travel enthusiast. Eat, think, and travel plenty.

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Penny Kim

Penny Kim


Marketing Director, photographer, world travel enthusiast. Eat, think, and travel plenty.