As I traveled down the so-called Gringo Trail through through Latin America, following roughly the Pan-American Highway that runs all along the entire Pacific coast, I hit upon an unexpected obstacle.

While all had gone well so far, Panama threw me a bit of a curveball. You see, as much as I’d like to continue my way from Panama to Colombia, it isn’t possible overland… at all.

The problem, you see, is this:

It’s called the Darién Gap: a dense jungle expanse with not a single road for over 160 kilometers.

There is no development or infrastructure here whatsoever. In this No Man’s Land, even the Pan-American Highway just stops, making any overland journey impossible. It’s a pity, because I had set my mind on avoiding flights during my journey.

Aside from the lack of roads, another issue is that the Darién Gap is brimming with smugglers and guerillas (not to mention hungry jaguars, reportedly). It’s one of the world’s major narcotrafficking routes and as such it’s very much no bueno.

Over the years, a few expeditioners have attempted to hike across, but the one consistent message you get is that you’d have to be crazy to do this.

How to cross the Darién Gap

So, as a backpacker just trying to get from Panama to Colombia, I had to find another way.

Flying is the most obvious answer. There are plenty of direct flights from Panama City to about half a dozen cities in Colombia. One-way tickets are typically in the $100 to $150 USD range.

However, as an overland traveller I preferred to avoid this. Fortunately, there is another way, and it’s much much better than flying…

Sailing boats regularly go back and forth between Panama and Colombia. These private boats pick up passengers — mostly backpackers and independent travellers — while also providing a kind of cruise experience while the sailing route passes the beautiful and remote San Blas Islands. The cost varies per boat/captain but is usually around $500 to $600 USD.

This is the only option without flying, as there are no public ferries or other transportation methods.

Booking my boat to Cartagena

I wasn’t sure how to find a sailing boat at first… I imagined having to go to a marina and asking random captains if they wanted a stowaway, but things are fortunately a bit more organized than that.

Blue Sailing is the main agency that helps the captains advertise their services. The boats and sailing schedules are all there, but this is not the type of thing you can just book online, so you’ll have to contact them directly through Whatsapp or e-mail.

I had left things quite late so several boats were already full. It meant staying in Panama City a few days longer than I had intended in order to catch the next available boat, so I recommend planning ahead for at least a week or so.

San Blas Adventures is an alternative option. This commercial tour company offers a somewhat different experience. The route doesn’t go straight to Cartagena after the San Blas Islands but docks at the remote and car-free village of Capurgana on Colombia’s Caribbean coast. In some ways it’s a less convenient entry point to Colombia, but I’ve also heard some wonderful things about Capurgana.

I personally opted for a private sailing boat direct to Cartagena, which is the most commonly taken route. A minivan took me to a harbor on Panama’s north coast, where my boat was ready to board.

This here is Gisbert, captain of a catamaran called the Santana, and the man who was going to bring me to Colombia:

Tip: as of 2023 the Santana is still sailing this route. If you want to reach the captain directly, you can do so at By booking direct he can offer you a discounted price compared to using the agencies.

Sailing through paradise

After meeting the dozen or so fellow passengers, 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… a fairly claustrophobic but still comfortable enough arrangement.

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.

We swam ashore to have a little look around. Strolling around the concrete landing strip lined with palm trees, I felt like it could have totally been a movie scene — perhaps a drop-off zone in some spy thriller. I was hoping for maybe a small propellor plane to land to complete the picture, but alas we had no such luck.

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

The departure point where we passed through immigration.

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…

John, the first mate on the Santana

Sun, rum and fun

The first 3 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, sea turtles, and an impressive two meter wide stingray that was just hovering over the seabed for at least an hour. Others 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 very 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! It may not sound like much, but I was loving these simple but filling meals.

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 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 to sell us crabs, lobster, and 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. Boat journeys have this way of creating a wonderful sense of camaraderie. I later ended up continuing my journey in Colombia with several of the other passengers.

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 faces 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.

I must confess though that the two days in the open sea were a bit challenging on my stomach at times! The waves can be a non-stop assault on your sense of balance.

We were luckily provided with anti-seasickness pills, which do make you very drowsy, so the last day was pretty quiet on the boat as most of us stayed horizontal. A few of us still got sick though.

That said, this was just part of the journey, and the days spent at the San Blas Islands — far beyond the range of any day-trippers from Panama City — made it utterly worth it.

The price of the trip may seem significant if you’re a budget traveller, though discounting $150 for the flight that you’d otherwise take, and counting about $30 a day for 5 days in expenses (food, lodging) that you don’t need to pay for, you’re looking at only about $200 more for the opportunity to do this magical trip.

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, with its Miami-like seafront, I felt that wave of excitement knowing a brand new chapter of my journey was about to begin.

Trip originally taken in 2014. Article updated based on current information.

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