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Updated June 6, 2015: 3/5 accomplished, a fourth I’ve booked for this month. North Korea is still tantalizing.

I’ve passed the 55 country mark this year, but there’s still so much more of the world I want to see. I gave some thought to the top five countries I haven’t visited yet that I most want to see, and how and when I’ll fit them in, and I’ll share that here.

Sometimes my trip planning happens for reasons other than the country being at the top of my list:

• There’s a mistake fare or cheap award.
• There’s an incredible First Class product I want to fly.
• I want to check a new region off my list.
• I want to meet up with a traveling friend.

Those are all valid reasons for a trip or two, but I want to refocus and visit the countries where I think I’ll have the most fun and learn the most.

Beyond just thinking about going there, I’m coming up with a time and type of miles to use. Just the act of making a plan makes it more likely I’ll follow through and finally get to these places.

1. Colombia: October 2014

Update: I went in October 2014, November 2014, and April 2015 to Bogota and Medellin. I want to return to Parque Tayrona and to do the Ciudad Perdida hike.

I remember the rumblings when I was on the gringo backpackers trail through Peru in the summer of 2007. Most of the backpackers had not been to Colombia as the country had had a terrible reputation for killings, kidnappings, and terrorism for years, but the few who had been were unanimous: Colombia was their favorite country of the trip.

Everyone had a different reason–Cartagena and the Caribbean, the mountains, the nightlife–but everyone agreed. The seeds were planted then, but somehow I never got around to seeing Colombia even as I visited farther afield countries like Paraguay and Bolivia.

Colombia has been at the top of my wish list since 2011 when I had a big map of South America on my wall and sketched a possible trip where I’d land in Maracaibo, Venezuela, cross the border to Colombia and do a trek to the Ciudad Perdida, visit Cartagena, Bogota, Cali, and Medellin, then head home.

Back then, a great deal came up on a cash ticket to see East Africa and Turkey, so I scrapped the Colombia plan.

When I found out I’d have a perfect 2.5 week travel window this October, I knew where I wanted to go. I plan to travel to Bogota for the entire time to embrace slow travel and getting to really know one place instead of rushing through three (though I like rapid travel too.) I am expecting to love Colombia and to visit the rest of the places on my lost 2011 itinerary on future trips.

I’ll book my trip with American Airlines miles because of what commenters said in this thread.

2. Cuba: First week we lift the embargo, possibly before

Update: I went in April 2014 and am writing a six part trip report.

I’ve mentioned it to friends, but let me put out publicly, so that I am shamed if I don’t follow through: I am going to Cuba the first week the embargo is lifted.

Cuba calls me for a lot of reasons. I love all Spanish-speaking countries. I’m intrigued by its legacies of communism and autarky and how they’ve shaped the country. The beaches and cigars and food and music and legends of the glamor of the 1950s don’t hurt either.

I figure that going the first week the embargo is lifted will have the effect of beating the wave of American tourists that are sure to follow and change the country’s character.

I do know that there are ways to travel to Cuba now, both illegal and legal, and I may look into traveling to the island before the embargo is lifted. But, if I don’t make it before, I will make it in the first week after the embargo is lifted.

Who knows what the best type of miles will be? I would guess Avios from Miami to Havana for 4,500 Avios each way on American Airlines flights.

3. Latvia: June 2015

Update: Latvia is booked for late this month with Finland, Estonia, and Lithuania on the same trip.

If you slice up Europe into the British Isles, Iberia, Western Europe, Eastern Europe, the Balkans, and the Baltics, I’ve been to every region except the Baltics. Since I love all the other parts of Europe, I know I’ll love the Baltics.

Lithuania, Estonia, and Latvia have been almost-destinations for too long. I can remember a few times when I had a ticket ready to be booked, but went with another option instead.

That ends next summer. I want to spend late Spring in the warmer parts of southern Europe, and then head to Latvia, Lithuania, and Estonia in June.

The best miles to get to Europe are United miles because the Star Alliance has the best award availability to and from Europe.

4. Chile: January 2015

Update: Hiking in Torres del Paine National Park from December 30 – January 2 is the highlight of my year so far.

There’s a scene in The Motorcycle Diaries where the characters cross a lake from Argentina to Chile. I want to cross that lake.

[Further research indicates they might have crossed Lago Nahuel Huapi, which I actually have visited already! Oops! I still want to see more of Patagonia, though.]

It’s the most beautiful backdrop I’ve ever seen in a movie.

Last year, I got to sample the Lake District of Argentine Patagonia. This upcoming South American summer, I want to spend longer and go farther south in Patagonia.

I expect to get into Chile over land. But at some point I’ll use miles to move on to another South American destination. The best miles within South America are Singapore miles because any one way within the continent is 12,500 miles in economy and 20,000 in business. I get my Singapore miles from ThankYou Points.

5. North Korea: 2016

One of my favorite things about traveling is seeing places different than I’m used to–the novelty of the food, culture, language, and way of life.

No country is as unlike where I’m from and the rest of the world as North Korea.

I know that the tour I’d take would be very tightly controlled, so I won’t get anything like the “authentic North Korea experience,” but it’s still a tour I really want to take.

I wanted to go to North Korea in September 2014, but my brother nixed the idea, so we stuck to China and South Korea on that trip. I think I’ll have another chance in 2016.

For now, I can read this trip report to get me excited.

The tours start in Beijing, so I’d love to get there on Cathay Pacific with American Airlines or US Airways miles.

Where do you want to go? When will you go? With which type of miles?

If you don’t know the best type of miles, get a Free Credit Card Consultation in which I tell you the best type of miles.