A tour through Havana offers a behind-the-scenes look at Cuba’s thriving art and jazz scene.

Written by Michelle Lyn
Photography Michelle Lyn

Walking through the streets of Old Havana, every multi-hued crumbling wall, every woman hanging laundry on her balcony and every barefooted child playing baseball has a story to tell. An island in a sea of controversy, Cuba is more than just a conversation starter for right now; it’s at the top of everyone’s travel list. And if it isn’t, it should be.

The real Cuba, essentially forbidden to Americans for the last 50 years, is a vibrant, proud nation welcoming travelers with open arms. Now that travel restrictions are easing, people-to-people travel agencies offering guided tours throughout Cuba are emerging from the woodwork. Jazz tours, food tours, photography tours, even niche interest tours, like those centering around baseball, appeal to a wide variety of groups looking to experience Cuba before it all changes.

The outfitter Insight Cuba has been running tours for 15 years, and has found a delicate balance between a guided tour and an authentic immersive experience. Take their 6-day “Jazz in Havana” expedition, which is the perfect introduction to the country’s thriving art and jazz scene, with a substantive amount of Cuban history woven into the experience. Although shepherded by an American, the group benefits immensely from a local Cuban guide who leads them from start to finish.   

The trip begins in Miami, where those bound for Cuba board an American Airlines charter flight. Less than an hour later, they’re greeted by tropical warmth and blue skies at the José Martí International Airport, amid a number of Miami-based Cubans arriving to visit relatives, with gifts from the States in hand.

Arriving in Cuba is like going back in time. Iconic American cars—including Chevys in abundance—dating back to past eras serve as a constant reminder of how long it’s been since American products have been freely available. The lack of cell service and nearly non-existent Wi-Fi may unsettle some at first, but truly allows travelers to go off-the-grid and be present in their surroundings. 

A brief bus ride through lush countryside delivers tour-goers to their first stop in the small town of Jaimanitas, which has been transformed by the vision of Jose Fuster, a local artist who has a way with tile. It is Fuster who creatively lifted the spirits of the entire community by turning sidewalks, porches and homes into vivid mosaics, brightening what has long been considered bleak times.

Inspired by this first encounter with a Cuban artist, you will then proceed to central Havana to check in to the seaside hotel, Meliá Cohiba, which sits opposite the Malecón, an esplanade that runs along the coast of Havana. This is where you’ll first glimpse the Cuba of tomorrow, with hotel lobbies full of tour groups jockeying for reservations at the Tropicana.

Heavily scheduled days might provide an insider’s look at the Abdala recording studio, where some of the great Cuban musical acts like Buena Vista Social Club used to record, as well as a front row seat to a private jam session with young musicians at the famous underground jazz club La Zorra y El Cuervo, and a lesson on the roots of Latin jazz—all with Cuba Libres in hand, of course.

Then there are the many opportunities to experience the richness of Cuban culture—lunch at a paladar (a private restaurant run from someone’s home) while being serenaded by the sultry sounds of live Spanish guitar; the chance to see a coveted Cuban cigar rolled in a shop teeming with tobacco leaves overhead; and a leisurely stroll through colonial Old Havana, where you can stop and have conversations with curious locals eager to make new friends.

Although tour days are full, there are still moments to head out and explore on your own. One experience not to be missed is an afternoon cocktail at Hotel Nacional de Cuba. The grandest hotel in Havana, Hotel Nacional is considered a symbol of history, culture and Cuban identity. Constructed in 1930, the hotel exudes refined elegance and, in its heyday, attracted illustrious guests like Winston Churchill, Frank Sinatra and Ava Gardner. Take some time to sit out on the property grounds overlooking the Havana Harbor and lose yourself in the live music and the scent of muddled mint wafting through the air while sipping mojito after mojito.

Finally, in what is perhaps the most memorable experience of the tour, venture outside of central Havana to visit what is described as a cultural center, but is really one room on the ground floor of a home that has been converted into the neighborhood dance hall. It’s called Santa Amalia’s Dance Club, and after arriving around 9 a.m., you’re immediately handed a stiff Cuba Libre, then pulled onto the dance floor. You’ll spend the next hour swirling around the room, believing you can salsa. Most impressive is that this particular group of local dancers has been dancing together in this same room for the last 60 or 70 years. They created a haven where they could cultivate and maintain the essence of Cuban culture through song and dance, a place where time has stood still through good and bad, offering a respite from any hardships.

This same resilient spirit welcomes us, wholeheartedly, to embrace the beauty and warmth that is Cuba—sooner, rather than later.

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