My current journey started in Mexico many months ago with the goal of eventually reaching Argentina. I’m taking the so-called Gringo Trail all the way through Latin America, roughly following the Pan-American Highway that runs all along the entire pacific coast of Central and South America.

It’s all gone well so far, but in Panama I was faced with an interesting challenge. As much as I’d like to continue my way from Panama to Colombia, it actually isn’t possible.

The problem, you see, is this:

Image: Dan Perry

It’s called the Darién Gap: a dense jungle expanse with not a single road for over 160 kilometers. Even the Pan-American Highway just stops, making any overland journey impossible. Aside from the lack of roads, another issue is that the Darién Gap is brimming with smugglers and guerillas (not to mention hungry pumas, apparently). While over the years a few adventurers have attempted to hike across, the one consistent message you get is that you’d have to be crazy to do this.

So, as a backpacker just trying to do this journey overland as much as possible, I had to find another way. I could fly, of course, though I wanted to avoid this if possible. Fortunately, there is another way, and it’s much much better than flying. 

The answer is to find a sailing boat that will take you aboard. This is Gisbert, captain of a catamaran called the Santana, and the guy who was going to bring me to Colombia:

The best way to get around the Darien Gap is to take a boat around the Darien Gulf. There are no ferries or regular line services doing this, but a few enterprising sailing boat captains like Gisbert have set up in this region taking travellers from Panama to Colombia or vice versa. This stunning journey takes five days and is only a little more expensive than flying.

In Panama City I researched which boats would be arriving soon, and decided the Santana was my best bet. Just a few e-mails later I was all signed up to join the next trip out from a small island north of Panama City.

John, the first mate on the Santana.

Sailing through paradise

After meeting the dozen or so other travellers who I’d be sharing this trip with, we all got on board and found our designated sleeping areas. Mine was in the very front tip of one of the two hulls of the catamaran.

The Santana was anchored near a tiny island with just a few huts, an immigration office (or more like an immigration shack) and a tiny landing strip. Me and my new boat buddies decided to swim ashore to have a little look around. We strolled around the concrete landing strip lined with palm trees, which felt like it could have totally been a movie scene. I was hoping for maybe a small propellor plane to land as to complete the scene, but alas we had no such luck.

After our passports were stamped in the immigration shack, we were all ready to go.

Our departure point. This island only had a few huts and an immigration office, where we had to get our passports stamped.

If you make the journey with Panama as your starting point, the first three days of sailing are spent around some of the San Blas Islands. They’re incredible tropical islands, many of them completely deserted. As we sailed past the first of some of these little Castaway islands amid beautiful azure waters, I started to become pretty envious of our amicable German captain. While I’m sure running a sailing charter can be hard work, this place sure didn’t seem like another day at the office to me…

Sun, rum and fun

Our days were mostly spent sunbathing, swimming and snorkelling around the islands. The waters around San Blas are teeming with marine life: while snorkelling I saw loads of fishes, a sea turtle, and an impressive two meter wide stingray that was just hovering over the seabed for at least an hour. Some of my fellow passengers also spotted a nurse shark sleeping under some rocks.

It was great to be away from the internet for a few days, just having the whole day to relax, and not seeing another person in sight.

I was also incredibly happy with the meals on board the Santana. After months of living off Central America’s rice-and-beans staples, it was a joy just to have some home-cooked spaghetti bolognese or grilled sausages with salad and potatoes. Perhaps that sounds like nothing special, but these meals put a real smile on my face as I hadn’t had anything like it for such a long time.

On day two we were anchored next to an island that was actually inhabited. A family of local Kuna people lived here in straw huts, spending part of the year here mainly to harvest coconuts. They were wonderfully friendly people and we purchased some of their coconuts to make Coco Locos. Later we also bought some crabs and lobsters from some Kuna fishermen to cook for dinner. Two German travellers on our boat were also keen fishermen and we could thank them for some late-night tuna sashimi snacks.

Local Kuna people docking with our boat to sell us crabs and lobster. They also caught a hogfish.

One of the great things about being more or less trapped on a boat for a few days is that you quickly get to know your fellow travellers. I was back to travelling solo at this point of my journey, so it was cool to make some new friends again. The experience reminded me of taking the slow boat along the mekong through Laos a year earlier — boat journeys have this way of creating a sense of camaraderie, if you’re with the right kind of people.

We spent our evenings mostly playing games around the dinner table. We also sat outside on the deck, chatting with each other whilst enjoying the wind in our face and the sounds of the sea. I often looked up and watched the mast and sails seemingly fixed while the galaxy swayed back and forth in the night sky. I stared at the waves, mesmerized by the bright green bioluminescent plankton sparkling in the dark.

Someone gets targeted for a hit in a game of ‘Mafia’

Sailing with the Santana was wonderful, and a great way to bookend my journey through Central America. As we sailed towards the harbor of Cartagena, our destination in Colombia, I got that wave of excitement knowing a brand new chapter of my journey was about to start.

At first I was surprised to see Cartagena looked more like Miami than the pictureque colonial town that the travel guides had described. But when later the old forts and town came into view, I knew we had arrived in South America.

More about the San Blas Islands

To learn more about the San Blas Islands, including info on the different beaches, marine life, weather/climate, accommodation, and more background on the Kuna people and their culture, I recommend checking out

How to cross the Darién Gap

There are basically 3 ways to cross the Darien Gap:

  • Sailing. I can definitely recommend this option. You can ask around about departing boats at hostels or harbors in Panama City or Cartagena, or check out or for online booking options. The cost is usually around $550. Check the descriptions to make sure the atmosphere will be what you expect. I avoided going on a sailing boat known to be an extreme party boat and opted for a chilled out vibe instead.
  • Speed boat. There’s a San Blas Adventure tour which takes you by speedboat, during which you’ll be mostly sleeping on hammocks on the islands themselves. This costs $375, which seems like a bargain in comparison, but know this is a very different experience (based on what people told me, you’ll be roughing it a lot more). You will also end up only just beyond the border in Colombia and not in Cartagena where most people want to be. The connection ferries and buses to Cartagena can take a lot of time and money, so this option may not be so cheap in reality.
  • Flying. The cheapest ticket I could find was $350 between Panama City an Cartagena. However this may have just been a lucky find; flights on most routes between these countries typically cost around $500 (one way).

There is currently no reliable or permanent ferry, nor would this be a good option as you would miss the San Blas islands entirely!

Some links may be affiliate links, meaning I may earn commission from products or services I recommend. For more, see site policies.