For almost 50 years Butterfield & Robinson has been leading adventures that “amble where others stride, bike where others motor and sip where others quaff.”  As a Canadian company, members of the B&R family have been traveling to Cuba for years. With restrictions loosening and the doors finally opening to Americans, they sent B & R Trip Designer Tyler Dillon, an American, to Cuba to research a country 90 miles off the coast of Florida that feels to most Americans like a world away. Here are Tyler’s travel diaries that he was kind enough to share with Daytripper365, chronicling his impressions of the place—both before and after his arrival.

Before the Trip: I am an American, and I am going to Cuba. I should have gone years ago to flex my right as a human to explore our home planet; now I’m seemingly only going because I have permission. But I am going and I am excited about it, and I don’t know why, but I am glad I am going now. It could be voyeuristic, it could be to see the old cars and moldy buildings, the same way I fell in love with Yangon all those years ago. It could be to brag, to travel selfishly, to establish some barometer for when I inevitably go back years from now and can say, “I remember when…” like seeing a band before they get big. But I hope I can run that through my system in the airport before I land, and land selflessly and open, to witness, to breathe in and embrace the unknown. I am heading down in a week and I am nervous, and excited, and will walk and make judgments as travelers do. I will also be changed; I’m not sure how at this point, but that not knowing is the part that interests me. I don’t know if I will like it, I might hate it, I might love it, I might be indifferent to it, it is pure potential at this point. That’s true of any future event I suppose, but travel has a way of shocking us into this realization, and Havana will certainly be shocking.

Canada’s Florida: I am an American and I am going to Cuba. Getting to the party at 2 a.m. after everyone else has been there all night—seeing, dancing, experiencing. My Canadian wife lived there and will be going back to Cuba, and many of her family have been going for years, alternating between Florida and Cuba depending on the mood. It is Canada’s Florida. Dwell on that for a moment. Can you imagine if it was illegal for Canadians to go to Florida, and all of a sudden it opened up and everyone was going on and on about how excited they were to go to Tampa, or Naples, or Orlando? We in the States may not fully understand the impulse, as we’ve never been locked out of that particular room in the house. But we have been locked out of the shed in the backyard, and alas the key has been found. The lights are still off, but we’re all peering in, ready to turn the lights on and see what we find. Will I find Orlando? God I hope not.

Initial Impressions: This is a whole country so close, and yet so very different. It is large, and varied, and if I was born here, I would be proud. It’s a pride similar to that seen in the Irish culture—they made it through to the other side. Whether or not the tide of capitalism slammed them, they proudly stood on principle, saying “No, this is ours and we don’t want you here.” But they do. It is the classic struggle between progress and preservation, one I am still unsure of. I keep wondering why I don’t have jetlag, because it reminds me so much of Myanmar, minus the temples, and Buddhist softness. Havana is a living poem of a place, filled with thin walls, music, smells, community, poverty and the educated. As in Buddhist Yangon, an educated population makes do with limited material things—a unique combination. Not to say it isn’t soft here—the people have been so kind to me and my family, asking about our baby, asking about our lives, not out of jealousy or some perverse interest in how the other side lives, but simply out of earnest kindness. It is refreshing. The people have been so kind to my family asking about our baby, asking about our lives.

The Dream Exists: There is a city in my mind that I had been looking for every time I went to New Orleans or Cartagena. These two cities have a past so rich you can feel it dripping off the walls, and see it in the airbrushed shirts for sale on the streets. Havana does not have this-- it still is this. Yes, it is looking back at its glory days in happy remembrance, but even its present feels like another era. I had no idea. I had spent years flying hours over oceans to get to something I thought only existed a world away. Yangon stole my heart, and still has it, its Buddhism, its strange British feel, it patina. But Havana is its equal in the Americas. If I leave in the morning I can be here by lunch, a lifetime away from where I live. Had I known, had I been able, I would have been coming here since college, I would have moved here after school, or perhaps in the middle of school, and never returned.

The Cars: Everyone talks about the cars. The cars are in plenitude and it ain’t no joke. There are Buick Eights, and Cadillacs, and Ladas, circa West Germany. It blew me away that there were so many. I expected a few cars lined up in the main plaza, parked right in front of some graffiti of Che in the background, ready for a tourist to take a photo and then walk on. But they are all over, used not only as taxis to shuttle around bewildered tourists like myself, but by locals. It will likely be one of the first things to go, and probably soon, but for now it is amazing to see.

Experience: Then there are the streets and run down buildings and sense of rot and life. Lots to explore, lots of small alleys and roads, winding this way and that, creating that sense of wonder, like a rough-hewn Paris. The five-story building just high enough to give a sense of sublime goes straight only for a few hundred yards, then veers in one direction or another, and you see trees high above, sometimes growing out of the roofs of buildings. It feels like a play land and it is scary and inviting all at the same time. I think I am going to enjoy spending some serious time in this place.

Precarious Potential: They need to be very careful here not to miss the mark. There are seldom cities like this, in this part of the world; I can’t think of one in the Western hemisphere. It reminds me of Yangon, Beirut, Tangiers, and it has a huge potential to be something amazing, if it isn’t all ready. When the hipsters from Brooklyn get here something will be lost—though what that is, exactly, I can’t quite say. It is fortunate that Cuba is not a place that is full of crops, or in the middle of two oceans, like Panama, or Burma, with oil on the other side of the border. The smallness of this place and the feeling that it is inconsequential is to its advantage. It can set itself up like Singapore, or Hong Kong, a country that stands a center for ideas rather than products. That really is the dividing line between countries and regions these days—it is either a resource or a collection of ideas, China or Silicon Valley.

Local Thoughts: I talked with a woman named Pamela, an American living in Cuba for the past 18 years, and an artist in a family of artists. We talked about how things are going to change and how they are going to change fast. She was excited but very worried, as well--that all the things she loved about this place will be washed away in the motion. She hosts dinners for folks who are thinkers, movers and shakers, and introduces them to their Cuban counterparts, but she is scared that this will turn into a stale event, each evening opening her house to a crowd of people who are not interested in the thoughts, the interactions, the sharing, but more concerned with the prestige and the bragging rights.

Last Thoughts: My job is to bring this change, in a way. I am the one introducing the changers to the movers, I am helping the small leak in the dam to get larger, but I still believe this can be done in a good way. My job is a bit of theater yes, but if you let it, it can also be directing spontaneity, allowing for space, the cracks are where the light gets in, as Mr. Cohen sang. But I must not act without thought of consequence. When we decide to visit a place or hire a guide, it can change a place or a person, and thus change us as well. It must not be forgotten, this motion.