Highlight of lunch with a Cuban family: “The powerful connection we felt around their table and their efforts to improve their community.”

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. The experience surpassed what we could have imagined.

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. She made a point to see us several times during our stay. Their level of commitment went far beyond professionalism—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. They delivered far more than that. Some of the most memorable experiences included a private concert at the home of a celebrated Cuban guitarist (Molina), 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 to take home.

The food and drinks were exceptional, including the cooking class and rum tasting/mixology lesson we had. As good as those were, 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 Vinales, 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. His commitment was remarkable in ensuring our comfort and making sure our journey was smooth (when things we take for granted, like availability of gasoline, cannot be assumed in Cuba).

The trip could not have been more thoughtfully and beautifully curated. 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.

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. The experience surpassed what we could have imagined.

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. She made a point to see us several times during our stay. Their level of commitment went far beyond professionalism—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. They delivered far more than that. Some of the most memorable experiences included a private concert at the home of a celebrated Cuban guitarist (Molina), 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 to take home.

The food and drinks were exceptional, including the cooking class and rum tasting/mixology lesson we had. As good as those were, 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 Vinales, 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. His commitment was remarkable in ensuring our comfort and making sure our journey was smooth (when things we take for granted, like availability of gasoline, cannot be assumed in Cuba).

The trip could not have been more thoughtfully and beautifully curated. 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.

Bill Melamed and his husband Jamey Lundblad visiting Fusterland, the Havana home of artist Jose 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.

We were thrilled with our guide Diana and the driver, Pedro in Havana. She is smart, well informed, and fun. We loved our hotel, most restaurants. We especially liked the private musical performance, the artist Maisel Lopez. A perfect trip.