Some days, everything just goes right—even when you don’t have any right to think that it will. That Tuesday in Cuba certainly didn’t get off to a great start. The official agency steered our five-person scouting party to the all-inclusive Soviet-era mega-hotel with the mondo-buffet on the not-so-perfect north shore. We wanted the Caribbean coast. “Can’t be done.” We wanted boutique hotels in Cienfuegos. “They are all full forever.” We wanted to go where the motorcoaching hordes don’t. “But the industrial-size travel companies know what is best! Just look how many people they bring! They all are so happy!”

So our intrepid little band did what you never used to be able to do in Cuba: we ditched the pre-planned plan. And we headed south to make our own luck. Our local guide Manuel suggested we drop in on his friends Tony and Mailin at their finca in the Escambray Mountains because, as all good travelers know, when all else fails have lunch. No warning? No problem. Out comes Mailin with platters of olives and sausages and fresh bread. Somehow a bottle of red wine opened itself. Tony, it turns out, is a natural travel therapist.

Lunch in Cuba

We bemoaned the crowds in some places. “No tourists come here,” he said. “Bring your friends to our home.” Are there any paths we could walk to get there? “No,” he said, grabbing his machete. “But I can make one.” And he took us to a vantage point overlooking the river that cuts through his property, where he used his machete to trace a trail-to-be that will start at the waterfalls, pass the neighbors’ coffee plantations, and wend back to this very table for lunch. Did I tell you how much we love Tony, Mailin and Fendi, their onesie-wearing chihuahua?

But still there were no hotel rooms in Cienfuegos. Tony again: “Did I mention my friend who is in charge of all hotels in this part of Cuba?” Fast forward to our impassioned pitch to officialdom over breakfast the next day, and suffice it to say that Classic Journeys has priority access to the best boutique hotels in town. Our luck lingered in Trinidad. A beautiful colonial town, it is. Pastel buildings, golden sunlight, cobbled streets. We happened on to a run of steps (like the Spanish Steps in Rome) just as the musicians started to play. None of us had to say “what if.” We knew it was a Classic Journeys moment that we could and would come back to again and again.

Cuban hotel

At the Bay of Pigs, most people do the museum and move on. Hungry (are you sensing a theme?), we drove an extra 20 minutes to Playa Perdiz—which, as it turns out, has a pristine coral reef perfect for snorkeling. Add one splashy activity to the itinerary, please.

Even in Havana, which we have visited too many times to count, we made a fantastic new discovery on this scouting trip. You know about the cult of classic cars in Cuba, I’m sure. In search of a tail-finned ride one day on short notice, a friend directed us to the Nostalgic Cars workshop. It’s an only-in-Havana collective of car fanatics, kind of a clubhouse/garage. Long story short, they’ve invited us back with our guests to talk cars and then hop in for a top-down cruise to Revolution Square and other sites in the city.

Car workshop

I’m super-excited about our new trip to Cienfuegos, Trinidad and Havana. We took some chances, made some connections that we already treasure, and created one of the most unique Cuban itineraries anywhere. If you come with us, I promise that you’ll experience Cuba the way we did…and nobody else does.