What happens when you get blissfully lost in Trinidad, Cuba

written by Jen Welch April 1, 2017
Trinidad Cuba

It’s always a risk setting down the guidebook and venturing out alone, but when I did so in Trinidad, it became one of the most memorable days of my Cuban adventure. I discovered local food, met a local man on a mountain who showed me where to go for an even more authentic local experience, and so much more…

When you meet seasoned travelers on the road you often hear them disregarding Lonely Planet recommendations and Tripadvisor’s top-rated restaurants, claiming that these are “too touristy”. It sounds smarmy, but they’re right – the top-rated restaurant is always more expensive and overcrowded, because you weren’t the only person reading those reviews. The best way to have a real adventure is to rid yourself of expectations and figure it out for yourself (hint: local Cubans i.e. Intrepid guides make that easy…). And that’s what I did in the perfectly-preserved town of Trinidad.

Cuba Trinidad colonial


Myself and a friend were a little hungover, and in 80+ degrees Fahrenheit, a milkshake was all we wanted – a refreshing, hydrating beverage. Bruce Lee once said: “A goal is not always something to be reached, it often serves simply as something to aim for”. I don’t know if he went backpacking much but that line is so relevant to life on the road. You can aim to achieve something with your day – like find a milkshake, for example – but in a developing country like Cuba some factors are out of your control.

Cuba road

We did pretty much a full circuit of the town to find one, being sent in a million different directions each time we asked someone new. This was no hardship since this town is a maze of picturesque cobbled streets, dotted with colorful Cadillacs and horses hiding in the shade – being lost here is an absolute pleasure. We concluded that everyone was either lying about where the milkshakes were and/or didn’t understand us. It didn’t really matter…

On our travels we also found a little hole in the wall serving food, a queue of locals forming. There was only one thing on the menu. Well, there wasn’t actually a menu at all, you just told them how many you wanted, and what you received was a bowl of pork, rice and spinach. It was delicious.

Hoping to burn off these newly acquired calories, we walked up what the locals call ‘the mountain’. This was a vast overstatement – no way would it qualify as a mountain – but we certainly broke a sweat. Taking the path straight up from Plaza Mayor, cobblestones turned into a dusty track, and at the top of a 30-minute incline sat a Radio Tower. From here you can see 360-degree views of the surrounding countryside, and it is well worth the sweaty walk (I’d recommend going in the morning before the sun gets too fierce).

Cuba Radio Tower

The view from Radio Tower

Even better than the view is the Cuban dude who sits up there with his dog, waiting eagerly for people to arrive thirsty and tired. He sells cold, refreshing beverages (“Finally!” we thought, still sad about the milkshake). Our new friend took us up a rickety ladder to a higher vantage point, where with a shabby yet functional pair of binoculars he pointed out sugar plantations in the nearby Valle de los Ingenios, as well as the ceramic plants that supply the town with its trademark rustic roof tiles.


Through the binoculars he also pointed out a river where locals were swimming. Being pretty damn hot in this sun we thought that taking a dip sounded like a great idea, so once he’d told us which road to take, off we went! Near Trinidad there are some lovely beaches if you fancy a swim, but this seemed like a great alternative.

We walked down a dusty track out of town for two or three miles, passing locals splish-splashing in various little streams, cooling down their horses and themselves. They say that time has stood still in Cuba for decades, and nothing conveyed this better than seeing locals using horses as a mode of transport like we would a car.

Cuba Trinidad horses

We made it to a river running underneath a bridge that has once been used for a train track. We assumed it was disused as there were a number of children sitting casually on the tracks, dangling their legs above the water below. We clambered down to the water’s edge and swam in the pool.

Let me tell you, nothing cures a hangover like being submerged in cool water. A truck drove down to the water at one point and stopped, and we thought he was figuring out how to cross the river, but it turned out he was there to wash it, just like the horses we passed earlier.

We were surrounded exclusively by locals – we hadn’t seen one other gringo along the path since we left town. It was a wonderfully authentic view of Cuban life, cooling down in a river rather than a white sand beach where the cocktails come hand-in-hand with the sun loungers. Eventually we came up from the water and crossed back over the rickety bridge to head back into town, satisfied with our discovery of so much more than a milkshake.

Tempted to see all of Cuba’s highlights (including Trinidad) for yourself? Check out Intrepid’s 15-day ‘Best of Cuba’ tour.

US citizen? This 9-day ‘Hola Cuba’ trip is designed just for you!

Image Credits (top to bottom): colorful Trinidad c/o Intrepid Travel, all the rest c/o Jen Welch

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