What one American traveler discovered on a cultural walking tour of Cuba—and why this is the moment to experience it thoughtfully, legally, and meaningfully.
For many Americans, Cuba exists as a headline, a question mark, or a long-held curiosity. For Elizabeth—who recently returned from a six-day cultural walking tour of Cuba with Classic Journeys—it became something far more enduring.
Some trips are enjoyable, some are memorable—but a rare few stay with you, gently rearranging how you see the world. This was one of those trips.
Cuba is not a destination you simply visit. It is a place you encounter—historically, politically, culturally, and deeply humanly. And for travelers willing to engage with it thoughtfully, Cuba offers something increasingly rare: perspective.
For more than two decades, Classic Journeys has helped American travelers experience Cuba legally and responsibly—through direct engagement with local people, independent businesses, and expert Cuban guides.
Why Travel to Cuba Now?
Elizabeth’s answer was simple—and one we hear often from our guests:
I wanted to learn, gain perspective, and support the Cuban people in a direct, meaningful way.
Cuba today is shaped by decades of history, economic hardship, and political complexity. But it is also shaped—most powerfully—by its people.
Traveling under the Support for the Cuban People license allows U.S. travelers to:
- Engage directly with local entrepreneurs, artists, chefs, and historians
- Support independent Cuban families and businesses
- Learn Cuba’s story beyond the headlines
This is not mass tourism. It is purposeful travel, designed to foster understanding, connection, and cultural exchange.
What Is It Really Like to Travel to Cuba Today?
Cuba is not a pampered destination—and that is precisely what makes it meaningful. Elizabeth is candid about the realities:
If you’re seeking comfort without disruption—constant connectivity or curated experiences—this is not the place.
Travelers should expect:
- Limited internet access outside hotels
- No U.S. cell service for most phones
- Occasional power outages
- Infrastructure shaped by decades of strain
And yet:
In the absence of convenience, something richer emerged: presence.
Without constant digital distraction, travelers find themselves more engaged—with their surroundings, their fellow travelers, and the people they meet along the way. For many, Cuba becomes a rare opportunity to slow down and be fully present.
The People of Cuba: Heart, Resilience, and Joy
Amid visible hardship, Elizabeth found what she describes as the true soul of Cuba.
And yet—amid all of this—the people are extraordinary.
Cubans are:
- Warm, expressive, and deeply social
- Creative, resourceful, and entrepreneurial
- Proud of their culture—even while frustrated by circumstance
Music, dance, and conversation are not performances here—they are daily life. In Havana and Trinidad, Elizabeth witnessed spontaneous joy that transcended age, race, and background.
In those moments, it felt like nothing else mattered.
Traveling this way—through personal encounters rather than staged experiences—creates moments of genuine connection that stay with you long after you return home.
A Deeper Understanding of Cuba’s History and Reality
This journey is as educational as it is moving.
Elizabeth reflects on Cuba’s past as a once-thriving nation, followed by decades of centralized control, scarcity, and limited opportunity. Learning this history—while standing inside it—offers perspective that books and headlines alone cannot provide.
Living inside that uncertainty—even briefly—forced me to confront how fortunate I am.
Through guided discussions, personal encounters, and expert local voices, travelers gain insight into:
- Daily life under communism
- The impact of sanctions on ordinary citizens
- Why meaningful change, if it comes, must come from within
This context transforms the way travelers understand Cuba—and often, the world beyond it.
Where We Went—and Who We Met
Elizabeth’s journey spanned some of Cuba’s most culturally and historically significant regions:
- Havana – private homes, classic car workshops, Hemingway’s house, salsa and jazz, and a moving visit to Havana’s cemetery
- Trinidad – colonial streets, a local chef’s kitchen, live music, and exploration with a local naturalist
- Bay of Pigs – snorkeling paired with historical context
- Cienfuegos – architecture, waterfront life, and local culture
Experiences included:
- A private salsa lesson
- A guided rum and cigar tasting
- Market visits and cooking experiences
- Conversations with artists, historians, and naturalists
This is Cuba experienced from the inside.
Is It Safe to Travel to Cuba?
Elizabeth addresses a question many Americans quietly ask.
Despite the hardship, crime is remarkably low… I felt safe at all times—arguably safer than I often do in the United States.
Cuba has:
- Extremely low violent crime
- No civilian gun ownership
- A strong sense of community and public safety
With expert local guides and thoughtful planning, Cuba is a destination where mature, experienced travelers often feel surprisingly at ease.
Traveling to Cuba from the United States: Common Questions
Is it legal for Americans to travel to Cuba?
Yes. Americans may travel to Cuba under specific licenses, including the Support for the Cuban People category. Classic Journeys ensures all travel is fully compliant.
Can I use credit cards or my phone in Cuba?
U.S. credit cards generally do not work in Cuba, and cell service is limited. Travelers are fully briefed in advance so there are no surprises.
Who is this trip best suited for?
This journey is ideal for thoughtful, curious travelers who value cultural depth, historical context, and meaningful human connection over luxury alone.
A Journey That Stays With You
Elizabeth’s reflection ends where many Cuba journeys begin—after you return home.
This trip did not end when I boarded the plane. It continues to live within me.
Cuba challenges assumptions, deepens gratitude, and reminds us of both the cost of ideology and the resilience of the human spirit.
Some journeys entertain.
Others transform.
Experience Cuba Thoughtfully with Classic Journeys
Ready to explore Cuba in a meaningful, responsible way?
Our small-group, fully guided walking tour is designed for travelers who value:
- Context over clichés
- Connection over consumption
- Learning over leisure alone
Travel legally. Travel responsibly. Travel deeply.
Planning travel to Cuba from the U.S.?
Traveling to Cuba as an American comes with important questions—about legality, safety, logistics, and what to expect on the ground. Our team is here to provide clear, up-to-date guidance, based on decades of experience operating legally under the Support for the Cuban People license.
Whether you’re curious about daily life in Cuba, how travel works from the U.S., or whether this journey is right for you, we’re always happy to have an honest, thoughtful conversation.
Explore Cuba
Cuba Travel Update: Classic Journeys Tours Remain Fully Compliant and Uniquely Authentic
By Classic Journeys
