Several years back when I decided I was going to go to every country, I had a rough idea which ones would be tough. That list has since, however, been totally turned upside down. Generally, I find that the “tough” countries are so for one of four reasons: safety, location/access, visas, legality.
Legality: There’s one big one here for US citizens: Cuba. I still haven’t done it, but I know that exemptions exist. I’ll likely buy into one of the cultural tours that are offered so I don’t have to do it another way, unless of course laws change which is always possible. Lots of folks seem to think it’s illegal to visit places the US doesn’t get along with, but that’s not true. Other than Cuba, I don’t know of any other countries the US government has a problem with me visiting.
Visas: Some countries just don’t like issuing visas to tourists. Belarus comes to mind, but that was pretty easy for me. I paid an agency to find someone to write a letter of invitation, paid them to get a visa, and piece of cake. I know it’s become a bit harder since then. Nauru can also fall into this category,because there just aren’t too many places to get the visa. I know Sudan also takes a long time to issue visas, and I plan to try later this year. Technically I’ve already crossed Sudan off when my Lufthansa flight made a stop there, but I want to see it as well. Guinea-Bissau has a pretty tough visa to get since there aren’t many embassies, but I had no trouble getting one same-day in Senegal last year. Unfortunately, however, I couldn’t make the trip. Libya is also really hard because they don’t issue tourist visas. I had no trouble, however, getting a business visa issued last year.
Location/Access: Then there are the places that are hard to get to. Tuvalu and Niue come to mind. Small pacific islands with just a couple of flights each week. There just aren’t too many options. Bhutan is also a bit difficult, but there are flights from Nepal, India, Bangkok, and as long as you buy into the government’s tourist requirements it’s not so hard. North Korea also isn’t easy, but again, go on a sponsored trip and you’re fine. This used to be much harder, but in the time since I went it’s become much easier. South Sudan also isn’t that easy, but once you’re there it’s an easy visa on arrival.
…and, the biggest group
Safety: I admit, when I started, this is the group I thought would be hardest. Iraq, Afghanistan, and especially Somalia came to mind. However, I’ve done all three of these now and never felt unsafe in any of them. I guess my definition of safety has changed a bit since realizing that even “unsafe” countries usually have a safer region you can visit. The one I still think I am going to have a really hard time with is Syria. No idea how I’m going to make that happen. I’ve also heard Guinea is pretty bad, so I doubt I’ll stay too long. Likewise on both of the Congos, but you never know. I’ve become a bit of a sucker for adventure.
That said, of the 60 remaining, I think the tough ones will be:
Algeria: notorious for long waits on visas, hopefully this shouldn’t be too bad.
Angola: hard to get a visa, and insanely expensive once you’re there
Cuba: with the US embargo, getting there legally will take some work
Eritrea: not real keen on issuing tourist visas, but supposedly it’s easy if you book with a local agent
Kiribati: few flights and remote, but doable
Nauru: see Kiribati
Nigeria: some security concerns, but with a friend working there I should be in good local hands. Visa shouldn’t be TOO hard.
Papua New Guinea: not exactly safe, but supposedly not too bad. Also, not super easy to get to.
Saudi Arabia: they don’t like tourists, but I’ve heard a transit visa is pretty easy now. Will try later this year.
Syria: this is going to be tricky. Active war zone, and difficult visas.
Turkmenistan: not real easy to get a visa as a tourist, but with a package tour it’s doable. Also, might have an opportunity with work.
Tuvalu: two flights a week – just hard to get to, and once there you’re there a few days!
Yemen: tourist visas seem to come and go, and it’s not always predictable. Mix in a bit of a security situation, and it won’t be easy.