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My trip through the Caribbean sounds like one paradise after another, but all the flights were mounting up so I eventually decided that I couldn’t literally see EVERY island in the region, I’d have to stick to the United Nations list of countries there – that meant no Puerto Rico, which technically speaking is part of the US, although that debate is for another day.

The Tres Palmas Inn
The Tres Palmas Inn

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However, navigating around the Caribbean isn’t quite as simple as I had thought, there are 13 countries in the Caribbean, but they aren’t all interconnected and there are almost no passenger boats running between them. Ouch. With a lot of time, and even more money, I managed to plan my route and the way it worked meant I would HAVE to go to Puerto Rico afterall, which meant getting my US visa online, organising hotels etc,  quite a hassle without feeling like I’m making progress towards my goal. Ok, I thought, let’s see what Puerto Rico has to offer me for one day and one night, I’ll spend it in the Capital, San Juan. And with low expectations, I flew from Saint Kitts (country 135/193) to Domincan Republic (country 136/193) Via San Juan….


Posters in the hotel proving it's my kinda place :P
Posters in the hotel proving it’s my kinda place 😛

I booked a gorgeous hotel, right on the coast, called the Tres Palmas Inn figuring that at least I’ll be sleeping in comfort and be ready for my next challenge. I had spoken to Edwin the amazing owner, via email and he when he heard about my goal he offered to pick me up from the airport personally. Wow, I thought, Puerto Rico is looking up.

Edwin and Me chowing down on some local food
Edwin and Me chowing down on some local food

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I had been on the road solo for the best part of a year by this point, and jetting through the Caribbean was giving me pangs of lonlieness, watching all the families, couples, friends enjoying paradise together while I was often sitting alone. One of those things that all travelers feel, but hopefully soon shake off so when Edwin picked me up at the airport with a HUGE smile and a welcome vibe I couldn’t be happier.

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Straight to the hotel I thought, I’ll chill, maybe swim, have dinner,  sleep, wake-up and fly to the Domincan Republic. Edwin had other ideas.

He was so pumped to show me San Juan in my little time that we didn’t even go to the hotel! We chatted the whole time in the car about my goal, and Puerto Rico, the beauty of its culture and he immediately made me wish I had actually planned to stay and explore. That was it, I would be tired for flight the next morning, Edwin took me straight to the old town in San Juan, explaining the history, telling me about his life, his business, it was like being with an old friend.

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Before long we were at an evening food market, where Edwin was showing me all the local food on offer, and not letting me pay a penny. Amazing. A few cocktails, some more beers – all local of course, more stories. My loneliness from the road had gone, I had discovered an awesome guy, a beautiful ‘country’ and a place I now want to get back and explore as soon as possible.

San Juan was much more beautiful than I had ever expected too, it’s a gorgeous mix of Cuba and Dominican Republic, with amazing old archecticture mixed with the vibrant Caribbean bright colours – amazing. And so different from a normal US style city that I had expected, so I owe an apology to all the Puerto Ricans out there – sorry guys, you come from an amazing place and I’ll be back as soon as I can.



Oh, and just for a little bit of extra excitement, a car drove into us on the way home, aaaah the life of a traveler. Finally getting back to the hotel I was really buzzing about my experience, especially considering my expecations. All my energy though quickly switched off when I got back to enjoy Edwin’s gorgeous hotel – the sound of the waves, the huge double bed, the hottub on the balcony overlooking the ocean, perfection.


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And only a super short drive to the airport in the morning, which in true Puerto Rican style,  was given to me by the security guard who was finishing his shift and ‘going kinda that way anyway’, and he wouldn’t accept a penny. Well played Puerto Rico – in twenty four hours, you won me over and then some.


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2 thoughts on “Transit in Puerto Rico, and Why I’m Rushing Back

  1. Had a great time in Puerto Rico, especially around Old San Juan and Condado. Rest of the island is really difficult to get around without a car rental, however. I’ll be back with the wife one of these days, there are often direct flights from NYC.

  2. Hi Johnny, I’ve just got back from Puerto Rico as well. That was my honeymoon. Really enjoyed Caribbean. Usually I travel independent on budget. This time I took a cruise. It was amazing experience. Have you ever tried it?

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