Disclaimer: This guide to “Can Americans travel to Cuba” was first published in Vacation Rental Travels Magazine Winter 2018 Issue reflecting regulations of 2017.  Click here for updates on legal travel to Cuba.

It’s been one of the most controversial destinations for Americans since the 1960s.  But love it or hate it, no one can deny that Cuba is intriguing.

Starting in January 2015, President Obama opened legal entry to Cuba for twelve new categories of American travelers. That’s when I started dreaming of going, and this year, that dream became a reality.

Some of the hype about Cuba is false; there are no old women smoking cigars on every street corner.  In fact, I never saw a single one.  Some of the hype is true; American classic cars are everywhere.

We wanted to see the “real Cuba,” now, before it changes.  The licensed “people-to-people” tours are expensive and adhere to a tightly-controlled, government-approved itinerary.  Since we qualified under one of the allowed categories, we opted to go on our own and rent a car to drive around the entire eastern half of the island.

Road Trip & Homestay Hopping

We also opted to stay in casa particulars – private residences that have been tailored and licensed to operate as bed and breakfasts – rather than the hotels which were widely reported to be run down.

There are different ways to experience a casa particular:

1. Entire house, owner not present.
2. Private room with private entrance.
3. Private room in the owner’s house with a shared entrance.

We tried all three, six homestays in all, in five different cities, with a range of hosts from those that spoke fluent English to no English at all.

What we lovingly call “The Mother of All Road Trips” started in Havana.  The capital city is almost indescribable.  It simultaneously assaults all your senses – the exquisite architecture now crumbling under your touch; the smells of cooking food wafting out from shops and homes mixed with the scent of garbage and dog excrement on the street; festive Latin music blaring from open windows compelling me to dance in the streets; the frozen daiquiri that slides all-too-quickly down your throat.

You can’t help but imagine how dazzling it must have been in its heyday…and yet, there’s something intoxicating about the glorious disrepair.

Old Havana

Our first casa particular was just a 10-minute walk from Old Havana, on the malecón, arguably the best place to stay in Havana.  The malecón is the boardwalk that runs along the ocean.  Our host, Jeannine, met us outside the building and escorted us into the rickety, noisy ancient elevator.  As the creaking iron grate doors slammed shut and we sluggishly ascended, I wondered what we’d gotten ourselves into.

Arriving at the top floor, we climbed a few more steps onto the rooftop terrace with one lone door at the end, which was our “penthouse.”  Entering the premises, I could not hide my glee. The apartment was spacious, modern, and bright.  The décor was cheerful, and I loved the contemporary furnishings and artwork.  Best of all was the spectacular birds-eye-view of the Atlantic Ocean, malecón, and multi-colored city buildings.

After getting settled, we walked a couple of blocks to a restaurant Jeannine had recommended, right on the malecón.  We chose seats on the second floor open-air terrace and treated ourselves to piña coladas, guacamole, and paella with views of the ocean in front of us and the ancient forts on the horizon. What a way to begin our Cuban adventure!

Old Havana mesmerized and fascinated me.  I could not get enough of it.  It’s a great walking city, with myriads stops.  The cafes in Plaza Vieja, the children feeding pigeons in Plaza San Francisco, drinking a mojito at La Bodeguita del Medio – Hemmingway’s old stomping ground, art, and souvenirs at Almacenes San Jose Market, Plaza de Armas, and El Floridita where the daiquiri was supposedly invented.  It’s a cacophony of sight and sound.

Vedado, or the “new (still old)” Havana has a different set of charms, including the Plaza de Revolution with the face of Cuba’s national folk hero, Ernesto Guevara, aka “Che” on the Ministry of the Interior building.  Che was a Marxist idealist and revolutionary, physician, author, and guerrilla leader and the Cubans adore him.  There’s the renowned Hotel Presidente overlooking the malecón, the open-air shops on La Rampa and John Lennon Park.

Cienfuegos

After a few days in Havana, we packed up our rental car and headed off to Cienfuegos, stopping briefly to check out the Bay of Pigs, the site of the failed military invasion to overthrow Fidel Castro’s communist government, and curiosity to most Americans.

Tip: WiFi is scarce in Cuba, and road signs are almost non-existent.  Before leaving home, we downloaded an offline app called Maps.me that really saved our bacon.

Cienfuegos is a port city on Cuba’s south coast and UNESCO World Heritage Site.  It’s known for its stunning colonial-era and neoclassic buildings and the well-preserved central square called Parque José Martí in the Plaza de Armas.  Here, in the central plaza, we ascended the windy spiral staircase in the cupula of the Palacio Ferrer building for incredible 360° views over the square and beyond.

Another highlight was visiting the Palacio de Valle, a neo-gothic mansion on the malecón, built in 1913.  The interior is intricately designed and decorated, and the rooftop bar has a turret and views across the city and bay.

Our homestay in Cienfuegos was on the 2^nd floor in the home of a local businessman and his wife.  After our day of exploration, we relaxed on the 3rd-floor terrace and watched the brilliant sun drop down into the bay while sharing cocktails with other guests.  We opted to have breakfast provided, and what we received was a feast that could easily have fed four people – eggs, ham, cheese, plates of locally-grown tropical fruit, coffee, fresh-squeezed mango juice, a basket of rolls, and a plate of fresh-baked Cuban cookies.  Our English-speaking host, Luis, and his wife could not have been nicer, recommending restaurants, road directions, and even giving us a complimentary Cuban music CD when we left.

Trinidad

I had been looking forward to our next stop, the pastel buildings and cobblestone streets of Trinidad.  Most of the city’s activities on our first day revolved around Plaza Mayor.  We sought out the iconic view of Trinidad – the La Iglesia y Convento de San Francisco and surrounding landscape. Climbing to the roof of the Palacio Cantero in Plaza Mayor, we were not disappointed.  The views were just as jaw-dropping as I’d seen in photos.

The morning of the second day was spent dealing with the remnants of my tummy trouble from the night before, but I’d recovered sufficiently enough to spend a delightful afternoon at nearby Ancon Beach.  The ocean at Ancon is variegated with crystal seafoam green near the shore and deeper turquoise blue further out. The water is as calm and as warm as bathwater and equally inviting.

Our casa particular in Trinidad was a whole house which we shared with another guest.  We had a small private room and bath on the second floor, and access to a rooftop terrace dining area, and a kitchen on the first floor which was shared by other guests and the host. The building was across the street from our host, Rene, who is a retired chef.  To be honest, this was my least favorite casa particular. It was too low-end for me, plus it took us longer to walk to the main square than advertised and the food prepared by the chef was good but not outstanding. We had a better and less-expensive meal in town. However, the room was really inexpensive, so for someone with a tight budget, I’d recommend it.

Varadero Beach

Off to Varadero Beach! I was very excited to visit Cuba’s only beach resort community.  Everything is relative; while certainly not upscale by American standards, Varadero caters more to the upscale tourists, and I really wished we had scheduled more time here.

The shimmering aqua ocean had white sugar sand and was fringed with swaying palm trees and palapas with beach chairs.  The effect was nothing short of dreamy.  It was just the place to chill out after a week of being on the road. Besides the beach and the shops lining the ocean boulevard, there’s not much to do as far as authentic Cuban experiences.  But we’d already had a lion’s share of history and culture, so I can’t emphasize enough how much I loved it here.

Since the accommodations in Varadero Beach are limited to hotels and all-inclusive resorts, we chose a casa particular about 10 minutes from the beach.  We had the whole first floor in the Blue Sky house – two bedrooms, kitchen, and living room with hand-carved furniture, as well as access to the third-floor terrace overlooking the ocean. We were also just a few minutes walk to a small bay where we enjoyed a pretty beach sunset.

Viñales

Heading to Viñales from Varadero, our next destination was an adventure in itself!  The first stop was Jibacoa Beach.  I’d read in one travel blog that it is the most beautiful beach in Cuba. I will tell you honestly, it was not. The color of the water did NOT look like the shimmering aqua depicted in that blog and was nowhere near as pretty as Varadero, plus there was the added nuisance of sand fleas.  But we salvaged the morning when we noticed the odd-looking trees on part of the beach.  We retrieved some props from the car and proceeded to have our own little photoshoot. We did have a lot of laughs as I struggled to get into a mermaid tail, shuffle several yards, and then hoist myself into one of those overhanging trees.

Back in the car to continue our trek, we chose an off-the-beaten-path along the coast, instead of the main route to Viñales.  It did take us a few hours longer, but the sights along the way were incomparable.  The narrow road, sometimes littered with potholes, sometimes nothing more than dirt ascended with the mountains and gorge on the left side and an endless ocean vista on the right side.  We shared the road with oxcarts, trucks, farm equipment, motorcycles, hitchhikers, and bicycles – sometimes all at the same time.  We passed one colorful tiny house and/or hut after another, all with lush tropical landscapes and flowers.  We would never have seen such sights had we stuck to the main thoroughfare.

The Valle de Viñales in Western Cuba is a lush, shamrock green basin of tobacco plantations. It’s the country’s second most-visited area after Havana, but you’d never guess it.  Viñales has a distinctly rural, laid-back vibe, authentic traditional Cuban culture, and a central street of colorful colonial buildings. Beyond the downtown, visitors can tour the tobacco plantations on foot or horseback, and visit the tobacco factories to see first-hand how the world-class cigars are grown and produced.

Our homestay was a one-story wooden structure with a terrace, typical of the area. The owners lived in the front of the house, but we had a separate entrance to our spacious room and bath in the back.  The house itself was absolutely adorable and beautifully landscaped.  But the most amazing feature was on the horizon – we were literally just steps from a tobacco farm and a backdrop of the mountains. Magical!

New Havana

Think you can’t find luxury in Cuba? Think again! Circling back to Havana, we wanted out last night in Cuba to be special. La Villa Teresa has to be the most gorgeous homestay in all of Havana! It’s a veritable palace with expensive period furnishings and highly detailed paint and décor. We had the entire suite on the third floor which included FOUR terraces. From the uppermost terrace, you have an incredible 360° view of all of Havana. If you want to feel like royalty, here’s where you stay.

The mansion is in a residential area of Havana, which is run down and crumbling, characteristic of Havana. The host, Jenny, and her Italian husband purchased the mansion floor by floor and renovated it to its former glory. They are hoping other Cubans will follow suit and begin the tedious process of reclaiming the neighborhood and restoring the rest of the mansions. La Villa Teresa is an amazing value for the money. I’d stay here again in a heartbeat.

What to Eat in Cuba

A big part of absorbing the Cuban culture is through its food and beverages.  Cuban cuisine is a blend of Spanish, Caribbean, African, and Native American recipes. Most of the meals we ate came with called “congri” black beans and rice cooked together, and roasted pork and chicken were the main meats offered.

You can’t go wrong with paella, a tasty entree made with Bomba rice, garlic, onion, peppers, saffron, paprika, white wine, adorned with either meat or seafood.  In fact, we liked the seafood paella so much we had it three times during our stay in Cuba.

The restaurants in Cuba do not have a reputation for having the best selection or freshest food, so many people opt to eat at paladares, restaurants in private homes.  Sometimes the casa particulars (private B&B’s) offer their guests home-cooked meals for an additional charge.  We did take advantage of the huge spread of breakfast foods and fruits not often found in the U.S., and an occasional evening meal if we happened to be back from exploring at dinnertime.

Guacamole is readily available as an appetizer or snack.  The Cuban guacamole we had was made from the Florida-type avocado rather than the Hass avocado; the Cuban guacamole is looser than traditional Hass guacamole and sometimes served with seafood on top.

Coppelia sells delicious ice cream in Vedado.  It’s where the locals go, and it’s really cheap, but be prepared to stand in a long line.   Perhaps a better way to obtain some of the creamy goodness is from one of the street vendors, sometimes driving a bicycle stand and usually extraordinarily friendly.

If you like to try street food, Cuba is a safe place to indulge because you can see it being roasted on a spit right in front of you, often the whole animal such as pork.

One funny experience was at Ache, a festive and friendly restaurant in Trinidad. Not seeing any kind of vegetable side dishes on the menu, we asked if they could make us a salad.  We did a salad….but it was cooked!

Our favorite dining experience was one we stumbled on by accident.  On the backroad drive from Havana to Viñales, we spotted a small but attractive, jungle-looking, palapa restaurant and decided to stop for a mid-afternoon bite.  No one spoke English and the menu was only available in Spanish, but somehow we managed to order a feast of breaded chicken, fresh-baked tortillas, beans and rice, fried plantains, and…. French fries.

What to Drink in Cuba

Old Havana

Rum plays a major role in Cuban cocktails. Here are some drinks you should not miss, and where to find them:

• Mojito – rum, mint, sugar, lime, and club soda. Go to La Bodeguita del Medio in Old Havana, Hemmingway’s old stomping ground.
• Daiquiri – rum, citrus juice, and sugar or other sweeteners. Go to El Floridita where it was allegedly created. Even if not true, if they were good enough for Hemmingway, they’ll be good enough for you!
• Cuba Libre – rum, Coca-Cola, sugar, and lime. Go to the Hotel Presidente on the malecón.
• Piña Colada – rum, coconut cream, and pineapple juice, blended. Go to Castropol on the malecón.
• Cristal – cerveza (beer). Go to La Vitrola at Plaza Vieja in Old Havana. It’s colorful and festive, and people-watching opportunities abound.

La Bodeguita del Medio

And naturally, there is one ultimate Cuban experience.  Though not technically categorized as either food or drink, it is nonetheless something that goes in your mouth.  The pièce de résistance…

The Cuban Cigar.  Boom.   

Cuba’s Time Warp

After the end of the revolution of 1959, the time has seemed to stand still in Cuba.  Once grand buildings now stand in a crumbling state of disrepair.  Home décor is scarce, so the homestays are decorated with outdated, shiny bedspreads, old-fashioned religious statues and wall art, and linoleum flooring. WiFi is difficult to find and only available in a few public spots, not in individual homes.

Perhaps the most obvious blast from the past is in transportation.  It’s not unusual to share a major road with ox carts, scooters, and farm tractors – anything goes, including more hitchhikers than vehicles in some areas.

Naturally, I’d heard about the 1950s American classic cars, and was looking forward to seeing them.  I was not prepared for just how many there are.  They are everywhere, in every city and town, on every highway and dirt mountain road!

Since trade with the United States ceased after the revolution, ending the supply of American auto parts, car owners have to be creative to keep the cars going.  It’s a visually stimulating site – colors, the styles, the wide range of disrepair from cars barely able to rumble along, to autos so pristine they look like they’ve just left a car show.

Roberto, the driver of our spiffy magenta convertible said, “I have to keep my car running myself.  I’m not just a mechanic; I have to be a make-shift engineer. When something in my car breaks down, I can’t just buy a new part and install it.  Parts are not available.  I have to create a new part from scratch, by cobbling together materials I can find.”

Hats off to the ingenuity and tenacity of the Cuban people!

Conclusion

Our Cuban road trip was so much more than we’d imagined. At times it made us frenzied with excitement. At times it left us speechless.  This is the way to see Cuba.  This is the way to experience authentic Cuban culture and the Cuban people.

NOTE: Since this article was originally published in 2018, the US Government has prohibited travel to Cuba, at least for now. Please check the government website for updated information on legal travel to Cuba.

All photos ©Kary Kern.

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About the Author

Patti Morrow is a freelance travel writer and founder of the award-winning international blog Luggage and Lipstick and southern travel blog Gone to Carolinas. TripAdvisor called her one of “20 Baby Boomer Travel Bloggers Having More Fun Than Millennials” and she was named one of the “Top 35 Travel Blogs” in the world.

Patti is the author of the book “Girls Go Solo: Tips for Women Traveling Alone,” and has over 150 bylines in 40 print and online publications, including The Huffington Post, International Living Magazine, Washington Post Sunday Travel, Travel Girl, Travel Play Live Magazine, and Ladies Home Journal.  She has traveled extensively through six continents looking for fabulous destinations, exotic beaches, and adventure activities for her Baby Boomer tribe.