Here the Pan-American Highway is interrupted so classical hitchhiking by car does not work. The region is mainly dense rainforest, and partly marshland. It is a nature reserve, and is protected both under Colombian, Panamanian and international Law. Nevertheless a lot of logging goes on there as the parks lack staff to keep the huge inaccessible space under tabs. It is said that from the air you can see the loggin tracks coming within just a few miles of each other on each side of the border, so in all fairness a road could exist if the political will did exist to create one. The gap is also one of the homes of the FARC, and that is the main reason that it is a very bright idea for white-skinned blue-eyed hitch-hikers to stay as far away from it as they possibly can... This should not discourage anyone from getting around it though!
There are several stories of Hitchhikers passing around this region on the Pacific Ocean from Panama to Colombia or Ecuador. On the Caribbean side a high exchange of goods exists between the Kuna Yala territory and Colombia so you might be lucky and hop on a commercial boat, travelling in either direction, if you are in no hurry.
From Colombia to Panama
In Cartagena there are heaps of charter sailing boats and private sailors heading to Colon who will charge anything beween 100 and 1000 US$ to take you there, often with atractive little stop offs in the San Blas.
An alternative way of crossing in this direction is to head to the port city of Turbo, where a 50 US$ (in 2011) boat can take you to Capurgana, like with all the other payboats if the boat owner like you enough and you can talk your way in good, you might get a lift. After that, the same applies for travelling from Capurgana to Puerto Obaldia, a small village that works as a border between Colombia and Panama. Once you're in Obaldia, you might either pay about 90 US$ (in 2011) to fly to Panama in a small plane, or find one last boat into Panama, for example by catching a boat to the island of Caledonia, and then another to Carti, from where there are roads connecting with Panama. From Puerto Obaldia you can also catch a boat a little way down the coast to where a trail links to the road. The trail is said to last about 2 or 3 days walk, and it is not advisable to do it without a guide. The Kuna do walk it often though, that is what it's there for. The whole think is a feasible and enjoyable adventure whichever combination of methods you chose, especially if you do pass through the Kuna Yala (aka San Blas) islands which are simply breathtaking.
For anyone attempting to hitchhike a ride on a boat, the second method is probably the easiest. Cartagena is not a great place to hitchhike free boat rides: it's big, full of tourists (who will probably pay for their trip, unlike you), and it's not easy to meet some of the captains in order to ask them for the free ride. Not to mention that most of the boats departing Cartagena are either cruise boats or medium sail boats offering expensive tours through the San Blas Islands. These tours usually cost something between 250 to 500 USD, and not many captains are willing to forfeit such amounts of money. The Turbo>Capurgana>Puerto Obaldia>Colon route, on the other hand, consists of a series of short rides where you can most certainly take your time to talk to payboat driver. The rides cost 20 to 50 USD, and that's a much more reasonable price for attempting to talk the driver into letting you in for free. It has been done and proved possible by several hitchhikers, so you should get a better chance of success taking this route.
From Panama to Colombia
To hitch a boat get to the San Cristobal Marina in Colon, boat hitching is never easy so be prepared to wait days or weeks. There are 2 marinas (including balboa marina) in Panama City but chances for Colombia are lower. On both sides many boats go to the South Pacific and you also may get a ride through the canal as linehandler.
Another option that worked smoothly for Dargeron on 2012 is to travel to the small town of Portobello, not too far from Colon, where most of the sail boats heading for Colombia stop at some point. The main advantage of taking this route instead of hitchhiking in Colon is a sailor hostel and bar called Captain's Jack, where you can easily find and talk to almost every captain who stops in Portobello (mostly at the evening/night). That offers an invaluable help to anyone attempting to hitch a boat ride, as instead of a tense, two-sentence request at the port, you can actually meet the captains, talk to them, perhaps invite them to a drink, and slowly gain their acceptance.
The same is true for the small village of Puerto Lindo, where quite a few of the "backpacker boats" are anchoring and you might get to know Captains in need of crew once you're sitting in the café frequented by yachties and gringos. You reach this village (which Cha found to have two hostels in 2013) from Colón via Portobelo, from where you can hitchhike easily or take the bus going to Guaira and get off in Puerto Lindo (ask driver).
Of course, the reverse of the method discussed above also works. To catch a plane to Obaldia go to the aiport in Panama city. To get to Carti ask for the road to the Kuna Yala national park. From there boats into the San Blas are eratic but existant, although I'm not sure they would take anyone for free as they do come there specifically to pick people up. To find the trail you would have to follow the Panamerican as far south as it goes, and then head north to the coast in the comarca Kuna Yala. Then you will still need a boat to reach Obaldia (there is no walking there unless you fancy being kidnapped by FARC...)
User lukeyboy95 tried to cover the gap in March 2014 and had considerable difficulty leaving from Carti Island, and as such, would recommend against going here. Tourism has also caused the native people to develop a slightly ugly side. They wouldn´t allow me to camp, or even take photos. Much more preferable El Porvenir for larger cargo boats. Having sadly given up, lukeyboy95 took the paid speed boat which was priced $115.00 all the way to the Capurgana. This was non negotiable despite numerous attempts. Took 9 hours. Please note that you can go almost the whole distance towards Caledonia, which the locals paid $50.00, and from there it may be easier to pick up passing boats. Another update was from Capurgana to Turbo is now priced at $30.00 and the pier area has restricted access and immigration check passports, making it difficult to find rides from here too. Perhaps head towards Acandi, as it is less touristic.
- I Hitchhiked from Portobelo to Capurgana. The best bar to meet captains is called "Casa Vela", just ask the locals and you will find it. It might takes days/weeks but is doable. You can read the whole story on my blog https://searching4sal.wordpress.com/2016/05/22/an-island-called-south-america/ - Diastema81
Crossing by dinghy
There is several stories of people crossing by dinghy on the Argentinian hitchhikers forum.
There are some stories, from people who circumvented the Darien Gap:
-  crossed from Panama to Colombia by boat hitching
- themodernnomad crossed for free from north to south by boat hitching. Great story. (read it here on his website)
- Isa and Natasha did it with payboats and planes.
- Chael777 spent a few days on Carti Sugdub after arriving there with some Kuna natives, eventually meeting a Colombian boat captain who took him across.
- Keith crossed via the San Blas into Colombia in 2014, and wrote about it on his blog.
- Darién Gap in Wikipedia