The Caribbean island nation of Cuba has been on our bucket list for a while, and we’ve been eager to explore this fascinating country before any more US travel restrictions set in. For Shelly’s birthday we decided to embark on a family trip to Cuba for a unique and memorable blend of history and culture in this melting pot of Latin, African and Caribbean influences. This was not our typical family trip though – it took a substantial amount of planning beforehand. We first had to navigate the strict US travel restrictions (select the Support for Cuban people visa category), plan for monetary challenges (carry lots of USD, American issued credit cards don’t work there), and deal with transportation & logistical headaches (use viahero.com to pick a dedicated local Cuban guide as a travel concierge).

From immersing ourselves in the historic heritage of Havana’s vibrant streets, sampling the finest cigars in the world in Vinales, to soaking in the sun on the pristine beaches of Playa del Este – here is a glimpse into the 10 ways that we enjoyed our unforgettable journey through Cuba with our children.

1. Soaking in the sights of old town Havana Vieja

The best way to journey through the rich history and unique charm of Cuba is to start with a tour of Havana Vieja. The old town area is a fascinating treasure trove of historical and architectural wonders that have survived the test of time for over five centuries. The entire area and its fortifications are a UNESCO world heritage site, with numerous plazas and churches bearing testament to the Spanish colonial heritage of Havana since its founding in 1519.

We wandered among Havana Vieja’s dilapidated yet enchanting buildings, their once vibrant pastel colors peeling to reveal layers of history and years of disrepair. As we explored the alleyways we saw barely stocked grocery stores and shops, with strikingly empty shelves and the shortage of basic necessities reminding us of the stuttering Cuban economy and the effects of the persisting American trade embargo. It was sobering an surreal to experience the disparity in wealth and infrastructure on this island that is just a short 45min flight away from Miami – truly worlds and years apart.

Despite the reminders of daily hardship and squalor, the warmth and friendliness of the locals shone through – a testament to Cuba’s enduring spirit even amidst economic challenges. Their infectious energy was evident in all the sights, sounds and aromas we experienced while meandering through the cobble stoned streets of Havana Vieja.

2. Discovering Havana’s colonial & revolutionary icons on a city tour

Cuba’s is a history that is intertwined with revolutionary uprisings and conflicts against both colonial powers and oppressive regimes over the past few centuries. The history of Cuba has always fascinated us, so we decided to book ourselves a private city tour to get a glimpse into the Cuban people’s tumultuous past.

Our exploration started at the iconic Castillo del Morro, where the kids were enthralled by the centuries-old fortifications and the distinctive lighthouse that have guarded Havana’s harbor for centuries. Climbing over remnants of the fort walls and peering into rusted cannons transported us back in time to Havana’s tortured history of pirate attacks and naval battles.

Wandering through plazas adorned with statues of heroes from the communist uprising and passing by ever present propaganda posters, we were also immersed in Cuba’s 20th century revolutionary legacy. Reminders of the Fidel Castro led Cuban revolution abound everywhere in Havana – the most important of which are the Granma Memorial and the Museo de la Revolución. The Plaza de la Independencia immortalizes Cuba’s other revolutionary heroes – with memorials to Che Guevara and Camilo Cienfuegos flanking the giant paved square.

3. Walking along the Malecón waterfront

One of the highlights of our visit was a leisurely sunset stroll along the Malecón, which is Havana’s iconic seaside promenade. As massive waves crashed against the seawall, locals and tourists alike gathered to enjoy the cool sea breeze and get some respite from the stifling tropical heat. The kids had a blast running back and forth across the Malecon chasing the drenching spray from the waves.

4. Feasting our eyes on colorful classic cars

No visit to Cuba is complete without admiring the colorful array of classic cars that line the streets. These vintage beauties, meticulously maintained and gleaming under the Caribbean sun, capture the essence of Havana’s nostalgic charm. We also indulged in the classic car experience for ourselves, when we rented a blue and white 1957 Oldsmobile for a few of our excursions in Havana. And throughout our trip the kids really enjoyed spotting all the different colors and models of cars during our explorations in and around the city.

5. Tracking down Ernest Hemingway’s Cuban legacy

Ernest Hemingway found solace and inspiration in the vibrant landscapes and culture of Cuba, and his legacy in this Caribbean island nation is deeply intertwined with its history.

For literature enthusiasts a pilgrimage to Finca Vigia, Hemingway’s beloved home in Cuba is a must. Dubbed ‘Finca Vigia’, the home is surrounded by lush gardens and overlooks the hills of Havana. This was his beloved home in Cuba for almost two decades, and is where he penned some of his most famous works such as ‘For whom the bell tolls’, and his Nobel prize winning ‘The old man and the sea’. The house remains as he left it, with the preserved interiors providing a poignant insight into Hemingway’s creative abode. We saw Hemingway’s writing desk, his numerous hunting trophies from Africa, and even some original Picasso paintings that adorn the walls. In Cojimar, a quaint fishing village that inspired ‘The Old Man and the Sea’, we explored the sleepy fishing village sights that fueled his imagination.

Hemingway also left his mark on the lively streets of Havana, with multiple bars bearing witness to his preferred Cuban Rum libations. El Floridita was Hemingway’s go-to spot for his favorite Daiquiri cocktail, while La Bodeguita del Medio was his preferred bar for refreshing Mojitos. Today these are both tourist magnets, still serving up Hemingway’s favorite tipples, albeit at astronomically marked up prices that would have shocked him.

6. Cooling down at the beach

To escape the city heat on one of the days, we headed out from the city to Playa del Este for a relaxing afternoon at Mar Azul beach. The views were stunning – with turquoise colored waters and inviting soft sands framing the picture postcard views. While the waves were too strong for swimming, the kids still enjoyed building sandcastles and darting into the water throughout the afternoon. Meanwhile Shelly and I lazed under the shade of a beach umbrella with our chilled drinks – the perfect way to unwind and soak in Cuba’s natural beauty.

7. Taking a trip to Viñales

Venturing beyond Havana, we embarked on a scenic trip to the Viñales Valley, a UNESCO World Heritage site renowned for its stunning landscapes and tobacco plantations. As we left Havana the scenery quickly morphed from dense cityscape to verdant countryside, and we were soon surrounded by views of farmland and grazing livestock. After about 3 hours drive, we arrived at the Mirador viewpoint, and were rewarded with breathtaking panoramic views of Viñales valley.

As we continued on towards the town, it was akin to stepping back in time – with more horse & bullock driven carts than cars making their way around bumpy pot holed roads. Viñales is a quaint little town mainly catering to tourists, dotted with family-run guesthouses and hostels. Staying there was a great way for us to experience the rural tranquility and simplicity of life in the Cuban countryside. We even got our first taste of the famed Cuban electricity blackout that night, and probably spent more time fanning ourselves and swatting mosquitos away than sleeping.

8. Sampling the finest Cuban cigars straight from the farm

A visit to Cuba wouldn’t be complete without sampling its world-famous cigars. At El Arado Ranch in Vinales, we learned first hand from a local farmer about the labor intensive cigar production process. We saw the plantations where the best tobacco in the world is cultivated, visited the multi-storey sheds where the leaves are dried and cured, and eventually witnessed the meticulous process of how each cigar is rolled by hand. Our guide shared that they are required to sell about 90% of their annual tobacco crop to the government, but they are able to produce cigars from the rest and sell it directly at the ranch. Shelly and I were then able to sample some fine Montecristo and Cohiba style cigars straight from the source, dipping them first in honey similar to how Che Guevara apparently enjoyed his favorite smokes.

9. Drinking all the Rum!

It would be remiss of course to visit Cuba without savoring the island’s iconic rum cocktails. The iconic Mojito was invented in Havana, while the Daiquiri takes its name from the town in southeastern Cuba where it was first concocted. We lost count of how many of these yummy and refreshing cocktails we sipped on and enjoyed throughout our visit, Salud!

10. Savoring the eclectic cuisine

Throughout our journey, we indulged in Cuba’s diverse culinary offerings in the local Paladares, which are privately run family restaurants. From sampling traditional dishes like Ropa Vieja (shredded beef stew) to indulging in fresh seafood (lobster is popular and surprisingly affordable), every meal was delectable. The kids particularly enjoyed trying new flavors and dishes, from crispy tostones (fried plantains) to the freshest pineapple and mango juices. In our Cuban culinary explorations, these restaurants were particular standouts:

 

La Guarida

Probably the most famous paladares in Havana, made famous through the Oscar nominated film “Fresa y Chocolate” (Strawberry and Chocolate).

 

Ajiaco Cafe

Farm to table cuisine with fresh ingredients from their own urban garden.

 

Havana 5

Fresh seafood at a rooftop restaurant overlooking views of Havana Harbor and Castillo del Morro

 

Doña Eutimia

Probably the best Langostino lobster that we had on our trip, in a nondescript paladares in old town