Cuba, shrouded in an air of mystery, often prompts a flurry of questions for many Americans eager to explore its vibrant streets and rich culture. “Can we travel there?” “Is it safe?” “How does one even get there?” Rest assured, the answer is a resounding yes, albeit with a few caveats.
The adventure to Cuba starts via daily flights offered by Southwest and American Airlines. There is a bit of paperwork to navigate before you go. A travel visa is essential, and may be acquired either in advance, or during the check-in process at the airport, before your flight. Cuba also mandates an Entrance Fee, a procedure that requires attention 48 hours prior to travel. Once approved, you’ll be armed with a QR code, your golden ticket upon arrival in the country.
Moreover, health insurance is required, and can be easily purchased with your airline ticket. With these formalities squared away, you’re almost ready to be on your way.
However, it’s crucial to note the unique conditions of American travel to Cuba. The days of breezy tourism are replaced by a list of 12 US government-approved categories, with “support for the Cuban people” being a popular choice for travelers. This isn’t just a phrase—it’s a commitment to immerse oneself in the local economy, by engaging with the Cubans in a manner that enriches their lives directly.
Embracing the essence of ‘Support for the Cuban people’ means forgoing the government-owned hotels and instead choosing to stay in ‘casa particulares’—private homes where your dollars contribute directly to Cuban families. It’s about savoring the flavors of family-owned ‘paladares’, restaurants that serve up authenticity on a plate, and seeking out private guides to unravel the island’s stories, ensuring that every peso spent fosters the community.
Capitalizing on everything I read in preparation for the trip, I also packed a duffel bag brimming with over-the-counter medications for both children and adults—a precious commodity in a country where such items are scarce.
Another complication of an American traveler bound for Cuba is the absence of financial banking relationships between the United States and Cuba. ATMs will not recognize your bank cards, your credit cards are useless, and cash becomes your sole monetary companion. This peculiarity requires a new level of trip planning. It’s essential to calculate your expenses for the entire duration of your stay from accommodation and meals to transportation and souvenirs. Bring crisp $1, $5, $10. Money can easily be exchanged for Cuban Pesos once you are there, but we didn’t need to. USD and Euros are widely accepted and preferred as methods of payment. I recommend advance booking as much as possible. Airbnb works as a convenient intermediary.
Embarking on this cash-only adventure certainly added an extra layer of anticipation for me. Admittedly, the thought of carrying all my spending money in my pocket was daunting. Despite these initial jitters, the moment we walked out of the airport and were greeted by a taxi waiting for us, anxiety melted away, replaced by excitement. We spent an incredible five days immersed in the culture and beauty of Cuba.
So, if you’re contemplating a journey to Cuba, let this be a nudge to embrace the challenge. Prepare well, pack your cash, and get ready to experience the island’s timeless charm in the most authentic way possible.
Day 1: Varadero: A Time Capsule by the Sea
Touching down in Varadero, I found myself stepping into what felt like a living postcard on the northern shore of Cuba. This resort town, often likened to Cancun, unfurls a 20-kilometer ribbon of beachfront adorned with a spectrum of all-inclusive hotels catering to every budget, and a quaint downtown with bars and restaurants.
As we were driving, I was immediately struck by the sense of time standing still. The vintage Pontiacs and Chevrolets, relics of the 1950s and ’60s, cruised the roads, as if they had been plucked from a classic film and set loose in the modern day, and I couldn’t help but wonder at the ingenuity that kept them running.
Our destination was the Royalton Hicacos, a luxury resort chain in Mexico and the Caribbean. My sister and her husband, having journeyed from Russia, were already waiting for us. Greeted with a refreshing welcome drink upon arrival, the tone was set for what was to become a nice stay.
Admittedly, this was my maiden voyage into the world of all-inclusive resorts. We have paid for the upgrades, and our rooms were spacious, comfortable, and we even had an exclusive use of the beach—a pristine stretch of white sand with water sports, relaxation, a bar with a small snack shack.
The evening unfolded leisurely, lounging by the pool and familiarizing ourselves with the amenities. We had a decent dinner at a resort restaurant. More adventurous spirits in our group ventured downtown to immerse themselves in the local vibe, while I was happy to catch up with my sister.
Transportation was easy enough with a bus service making regular pickups from the hotels to the downtown. Taxis, too, were readily available.
Day 2: Beach, Saturn’s Caves, and Matanzas
Sun, sand, and tropical cocktails! We soaked up the sun and had a lunch of grilled catch of the day at a beachside shack. With sandy feet and a change of clothes, we hopped in a cab to visit the Saturn Caves, which in essence is a cenote (a natural hole in the ground filled with a pool of crystalline waters). Named for the stalactites and stalagmites that evoke the imagery of Saturn’s rings, the cave was a cool respite from the sun. After a dip and a few photo opps, we relaxed with a beer and coffee at on site cafe before continuing to Matanzas, a capital of Matanzas province.
Our journey to Matanzas, however, was an unexpected adventure. A torrential downpour was no match for aging windshield wipers, and I found myself silently praying for safe arrival, a prayer that was thankfully answered.
Matanzas is a vibrant city, renowned for its Afro-Cuban roots and a strong influence on music, dance and religious traditions. There was an authentic, unfiltered vibrancy to the city, and yet, a poignant undercurrent of poverty was impossible to ignore. Store shelves stood starkly bare, save for the offerings of cleaning products, rice and canned beans.
As we roamed the streets, the spontaneity of Cuba manifested when a local woman seized the moment to pull my son into an impromptu dance, the rhythm of the streets guiding their steps. As the day wound down, our driver, ever patient, returned us to our home base in Varadero, and dropped us off at Terraza Cuba, a restaurant recommended by the hotel staff. The menu offered a medley of Cuban specialties, with good service and live music. But as the saying goes, all good things come with a price. Terraza Cuba was no exception.
The night was young, so we headed to downtown Varadero for some live music at the Beatles Bar before calling it a night.
Day 3: Beach and Music Galore!
Our last day in Varadero called for a day of relaxing on the beach. While we lounged in the sun, the boys decided to embark on an adventurous trip to Ambrosio cave, where they encountered bats and other creepy crawlies. After their expedition, they returned hungry, and we enjoyed a casual beachside lunch. We were debating about taking another day trip, but it was late in a day, and we settled on blissfully spending the rest of the day savoring every beachy moment. As the sun began to set, we followed another local recommendation, La Fiesta del Carbon, for an early dinner. This BBQ joint was pure tourist heaven, complete with a lively band serenading us at our table.
After dinner, we went back downtown, strolled along 1st Avenue taking in the local vibes and ending our night on a high note with a traditional Cuban music at Calle 62.
Day 4: Havana
Havana is a city that defies simple description; it demands to be lived, breathed, and felt firsthand. Some seasoned travelers insist that you need weeks, if not months, to truly grasp the essence of Havana. Yet, with just a 48-hour window, we aimed to skim the surface, to capture a snapshot of a city steeped in history and alive with energy.
We hired a guide with a driver for a 2 hour journey from Varadero and a city tour. We began at the Castillo del Morro, a bastion of Havana’s storied past, perched at the mouth of the harbor. Adjacent to this historical monument, we stumbled upon a treasure trove for cigar aficionados—the Cabana Cigar shop. Here, we had the privilege of observing a master at work: Jose (Cueto) Castelar, a name etched in the annals of the Guinness Book of Records for crafting the world’s longest cigar, an astounding feat stretching 81.80 meters (268 feet 4 inches). While the allure of Cuban cigars is undeniable, U.S. regulations do not allow the import of Cuban cigars or rum, and we had no desire to risk it.
Our exploration continued with a drive through the city’s heart, where the architecture tells a story of the past grandeur and grace. We wandered the cobblestone streets of Old Havana, pausing briefly at Floridita—a bar immortalized by Ernest Hemingway.
Yet, beneath the romantic veneer of this tourist haven, the realities of time’s toll are inescapable. Despite the vibrant façades and the lively atmosphere of refurbished restaurants, the signs of decay and hardship are palpable just beyond the tourist’s usual trail.
We stumbled upon Fonda al Pirata, a quaint spot to grab a drink, coffee and a well deserved break. We said goodbye to our guide and driver, and continued on our own with a leisurely stroll to ChaChaCha, a restaurant that had come highly recommended on my list of must-visit dining spots in Havana. The food lived up to its reputation—everything was delicious.
The next destination was an absolute highlight: Fabrica de Arte Cubano. The venue was an eclectic blend of modern art spread over two levels, pulsating with the rhythms of music that transitions into live performances later into the night . We arrived at around 9 pm, which seemed early, but it allowed us to witness the transformation of the space as it buzzed with energy and filled with an array of people. By the time we left just after 11 pm, a queue had formed outside—a testament to its popularity. We tried a few other spots on the way home, but eventually ended up at a restaurant not far from the airbnb, with live music and some rum for a nightcap.
Day 5: A Morning in Old Havana
The day dawned with a quick breakfast before we hailed a cab to Plaza Vieja, one of the oldest squares in another section of Old Havana. The morning was spent meandering through the streets, each turn revealing more of the city’s charm. Lunch was another memorable affair, culminating in a classic Havana moment—coffee and a cigar at Mojito Mojito. Our exploration continued at San Jose Artisan Market, a place filled with stalls for the last minute cheap souvenir shopping.
Our journey through Havana brought us again and again face to face with a stark reality that lingers just beneath the surface of this vibrant city. As we ventured off the main streets on our way to the San Jose Artisan Market, the scene shifted dramatically. The poverty was unmistakable; children reached out for spare change, and the streets were littered with uncollected trash and stench. This abrupt juxtaposition was jarring. On one hand, there was the Havana that catered to visitors with its manicured streets and culinary abundance, and on the other, just a few blocks away, was a Havana that struggled, where the daily fight for survival was an unavoidable truth. It was a humbling reminder of the complexities of this city, where beauty and hardship coexist so closely.
But our time in Havana was drawing to a close. My sister was set to return to Varadero to carry on with her vacation, while for us, it was time to pack our bags and head to the airport, our minds filled with the memories of a city of stark contrasts, a place of indelible beauty and undeniable challenges. As we took off, Havana remained below us—a city that gave us a glimpse of its soul, one that we would carry with us long after our departure.
