Homestay Hopping on Cuba

Article by Patti Morrow & Photos by Kary Kern

It’s been one of the most controversial destinations for American’s since the 1960’s. 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 dreamed of going, and last summer (2017), 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 twelve categoies, we opted to go on our own and rent a car to drive around the entire eastern half of the island.

We also opted to stay in casa particulars – private residences that have been tailored and licensed to operate as homestays – rather than the hotels which were 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, 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 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 blares 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.

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 birdseye- view of the Atlantic Ocean, The Malecón and multi-colored city buildings.

If Havana is your destination, The Malecón is the place to stay. Let Jeannine host your unforgettable stay in Cuba Click here for more information and book your stay.

After getting settled, we walked a couple blocks to a restaurant Jeannine recommended, right on The Malecón We chose seats on the second-floor openair terrace and treated ourselves to Piña collada’s, guacamole, and paella. From the terrace we had 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, El Floridita where the daiquiri was supposedly invented, Plaza de Armas. It’s a cacophony of sight and sound.

Vedado or the “new (still old) Havana” has a different set of charms. The Plaza de Revolution has 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.

Leaving Havana

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

Tip: Wi-Fi is scarce in Cuba, and road signs almost non-existent. Before leaving home, we downloaded an off-line app called that 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. The well-preserved central square is 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 2nd floor in the home of a local businessman and his wife. After our day of exploration, we relaxed on the 3rd floor terrace, and shared cocktails with the other guests as we watched the brilliant sun drop into the bay. . We opted to have breakfast provided, and received a feast that could 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.

Gaviota de Jagua with hosts Luis and Maria is a wonderful place to stay in Cienfuegos Click here for more information and room availability

The Streets of Trinidad

I had been looking forward to our next stop, the pastel buildings and cobblestone streets of Trinidad. Most of the city’s activities 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 bath water 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 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.

For the budget minded, Chef Rene and his Hostal El Capitan are a good choice. Click here for more information and to book your stay.

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 handcarved 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 (above).

A delightful place, The Blue Sky will welcome you to Varadero Click here for availability and to book your room.

On to Viñales

Heading to Viñales, our next destination was an adventure onto itself! First stop was Jibacoa Beach. The beach was a bit of a let-down – nowhere near as pretty as Varadero and, there was the added nuisance of sand fleas. But we salvaged the morning when we noticed the oddlooking trees on part of the beach. We retrieved some props from the car and proceeded to have our own little photo shoot.

We had a lot of laughs as I struggled to get into a mermaid tail, shuffled several yards, and then hoisted 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 took 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, traditional Cuban culture, and, a central street of colorful colonial buildings. Beyond 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.


This magical mountain foothill homestay awaits you! Click here for more information and to book your stay.

Luxurious 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.

This pristine mansion is in a residential area of Havana which is run- down and crumbling, is 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.

The La Villa Teresa is a terrific place to stay when visiting Havana Click here for more information and to book your stay.

This is the way to see Cuba

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.

Cuba’s Time Warp

After the end of the revolution of 1959, 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, oldfashioned 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 1950’s 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!

Legal Travel to Cuba
Travel to Cuba for Americans was banned in 1960 when the United States imposed a trade embargo against Cuba. From the U.S. Deprtment of State website: Travel to Cuba is regulated by the Office of Foreign Assets Control (OFAC) of the U.S. Department of the Treasury. Anyone located in the United States, regardless of citizenship and nationality, must comply with these regulations. Individuals seeking to travel to Cuba are not required to obtain licenses from OFAC if their travel is covered by a general license. If travel is not covered by a general license, you must seek OFAC authorization in the form of a specific license. The lines for legal travel to Cuba are subject to rapid change. Before planning a trip to Cuba we highly recommend you consult with the US Embassy, the US Embassy in Havana , and the Embassy of the Republic of Cuba in Washington DC for details and requirements.

Patti Morrow is a freelance travel writer and founder of Luggage and Lipstick – a travel blog for baby boomer adventurers. She was recently named by TripAdvisor as one of “20 Baby Boomer Travel Bloggers Having More Fun Than Millennials), and is the author of the book “Girls Go Solo: Tips for Women Traveling Alone.” Patti has over 100 bylines in 35 publications, including The Huffington Post and The Washington Post. She has traveled throughout most of the USA and more than 50 countries and islands abroad.




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