Cuba: An Opportunity For This Spring
6 min readOver the years, policies around U.S. travelers visiting Cuba have swung back and forth; with a new administration in Washington, we may soon see that pendulum return to the side of greater restrictions—potentially outright bans. If Cuba has been on your list, this spring is a smart time to go. The next few months offer ...
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Over the years, policies around U.S. travelers visiting Cuba have swung back and forth; with a new administration in Washington, we may soon see that pendulum return to the side of greater restrictions—potentially outright bans. If Cuba has been on your list, this spring is a smart time to go.
The next few months offer excellent weather on the island, before the summer heat sets in. And since tourism to Cuba never really rebounded post-Covid, there is still good availability through April, even at the small, privately owned casas particulares with the highest levels of comfort and service available (plus backup generators to keep you powered through any blackouts).
Cuba is not a destination for travelers who expect everything to run like clockwork, and U.S. visitors can’t spend a day lazing at the beach. But curious travelers with a spirit of flexibility have raved to us about the richness of Cuban culture and the openness of Cuban people. And with Cuba’s economy struggling mightily, the money that travelers put directly into local pockets is more impactful than ever.
If you can’t get away until the fall, we know Cuba specialists who are guaranteeing refunds should new U.S. restrictions make travel impossible. It’s also reassuring to know that, during past policy shifts, already-booked trips that met the old rules were still allowed to operate.
Guided by the right Cuba trip-planning expert, you can meet internationally renowned artists in their home studios, enjoy private concerts by award-winning musicians, and cook beside a chef using the highest-quality homegrown and imported ingredients. (Of course, these are exactly the kinds of local experiences that the folks on our WOW List of Trusted Travel Experts arrange around the world.)
Read on to learn about the experiences your fellow travelers have had in Cuba. Ready to plan your own trip? Click the button below and we’ll connect you with the Cuba fixer who best suits your needs.
“Personal touches allowed us to experience Cuba through the eyes and hearts of the local people…”
The Cuban people are perhaps the country’s greatest asset. Photo: Shutterstock
“Our trip to Cuba in March 2025 was nothing short of extraordinary. What made it so special wasn’t just what we saw and the richness of the experience (though both were good), but the exceptional care and expertise with which every detail was planned.
From the very beginning, Rob and Ana Maria took the time to truly understand what we hoped to gain from our time in Cuba. Their thoughtfulness, in partnership with their phenomenal on-the-ground team, Raquel and Diana, made all the difference. Raquel met us at the airport and became our amazing guide and companion throughout our stay. Diana, our 24/7 concierge, partnered with Raquel to work magic behind the scenes to make sure every moment was seamless. By the end of the trip, we had met their families and were invited to attend Diana’s daughter’s birthday party. These personal touches allowed us to experience Cuba through the eyes and hearts of the local people.
We asked for a trip that would help us connect with the culture and learn about the people. Some of the most memorable experiences included a private concert at the home of a celebrated Cuban guitarist and a mural tour that was originally planned with the artist himself—who was unexpectedly out of the country. In his place, his wife welcomed us, hosted us for coffee, and shared stories of his work. In a thoughtful gesture, the artist left two original portraits for us to take home.
The food and drinks were exceptional, including the cooking class and rum tasting/mixology lesson we had. One of our favorite experiences was sharing lunch in the home of a Cuban family. The meal rivaled the top restaurants we visited, but what stayed with us was the intimate conversation and powerful connection we felt around their table and their efforts to improve their community. Another surprise…attending a local baseball game, which was unplanned and coordinated by the family we shared lunch with. It was another glimpse into the everyday Cuban spirit.
There was also a day trip to Viñales, where we explored tobacco and coffee farms and gained a deeper appreciation for the traditions and resilience of Cuba’s farming communities. Our driver during the trip, Tony, safely transported us around Havana and to the countryside (when things we take for granted, like availability of gasoline, cannot be assumed in Cuba).
The warmth, resourcefulness, and hospitality of the Cuban people was front-and-center in every interaction. We are grateful to Rob and Ana, Raquel, and Diana—not only for planning a perfect trip, but for welcoming us into their everyday lives. It was an experience we will carry with us forever.” —Anne Marie Bell
To get your own WOW trip, start with our trip questionnaire, reached via the black button below.
“Cuba is a country of contrast—beautiful but challenging, difficult but hopeful…”
Traveler Bill Melamed and his husband Jamey Lundblad at Fusterlandia, the Havana home of artist José Fuster.
“Rob, Ana and their team provided a memorable and wonderful week in Cuba. From the first outreach through the planning process, they worked with this group of four culture hounds (me, my husband, and two friends) to craft a unique and custom itinerary that allowed for so many memorable moments. Cuba is a country of contrast—beautiful but challenging, difficult but hopeful—and our week there allowed us to see, learn, and experience it all.
We had countless private moments with Cubans in their homes that built memories that we will carry with us. If Cuba is not on your travel list, adjust your list NOW and talk to Rob’s team about how to see this special country. We were there for a week (February 16-23) and loved it from beginning to end. We were especially happy to be out of Havana and see more of the country, including Santa Clara, Trinidad and Cienfuegos. Go if you can, you won’t regret a minute.” —Bill Melamed
To get your own WOW trip, start with our trip questionnaire, reached via the black button below.
“A fascinating country whose people manage to deal with numerous issues resulting from their political structure…”
The Cathedral of Santiago de Cuba. Photo: Shutterstock
“Recently returned from a 12-night stay in Cuba. Cuba is a fascinating country whose people manage to deal with numerous issues resulting from their political structure. Our visit enabled us to meet with and speak freely to a cross section of the population. This enabled us to learn a great deal about the culture, history and current state of affairs in Cuba. We visited three different cities; saw many of the traditional tourist sites; enjoyed several excellent restaurants; hiked the numerous nature pathways; experienced the power outages; observed the gas shortages; and traveled many roadways along with the horse and wagons. But the lasting memory is that of the Cuban people struggling with the decision: Do we stay or leave Cuba.
Our thanks to Jose Miguel who traveled with us; ate dinner with us nightly, introduced us to his family and the many Cubans who are his friends. He enabled us to learn a great deal about Cuba, for which we are grateful. Highly recommended, but don’t expect ‘creature comforts.’” —Joe Rothman
This trip was arranged by a WOW List candidate. Here’s what that means.
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