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Part of the fun of the miles and points hobby is the planning. Whether it is planning an actual trip, or the next killer card bonus to get, I find my mind is in travel hacking planning mode a lot. It’s honestly hard to turn off.

I’ll often search flights just for fun, both revenue fares and award seats. There is no such thing as too much research. I visit Google Flights nearly every day, for at least a few minutes (SEE: 6 reasons Google Flights is the BEST flight search engine).

The side effect is that I often find myself dreaming up new trip ideas. I am sitting on quite a stash of miles and points (SEE: Mid-year inventory: we have how many miles and points?), so it isn’t hard to find *something* to do with them. Earn ’em and burn ’em, they say. And they are burning a hole in my pocket.

Speculating an around the world trip

I’m probably crazy. Actually, I know I am crazy. My wife and I just got back 2.5 months ago from Costa Rica where we finalized the adoption of our three kids. Our lives have been on major change mode lately. But is it too much to think I might be able to take 2 of my kids on an around the world adventure?

My first foray into traveling with our older two children was in December. We spent a quick weekend with my grandparents in the foothills of the Sierra Nevada mountains. The kids loved the whole experience.

SEE: Escape Lounge Oakland review – a surprising find

SEE: Boutique Air flight review: the closest I’ll ever come to flying private

a boy and girl sitting in a plane

After that we did a quick overnight for New Year’s. We just got back yesterday from a long weekend in the Sacramento area. Next week we go to Disneyland. Our kids already seem like pretty good little travelers, so I’m feeling bullish on what else I could plan.

But an around the world trip is much different than weekends away by car. The length is much different. There’ll be new cultures, new foods, and far more foreign experiences. They have adapted well to life in the U.S., but this warrants a lot more discussion before I pull the trigger. But if I did…

Working with those sweet spots

When planning a trip, I often focus in on the sweet spots of each program. Depending on how we structure things, we could cover a good number of destinations on relatively few points. I’ve considered just heading  to Europe or Asia for a week or so, but I know I could easily do much more than that. I’m specifically looking at:

  • San Francisco to Tokyo with a free stopover in Hong Kong in business class, using 50,000 Alaska miles
  • Tokyo to Helsinki via Doha (where we could hopefully spend a day sightseeing) on Qatar for 45,000 Asia Miles per person. This is a screaming good deal (SEE: 6 best uses of Asia Miles) for the amount of flying.
  • Helsinki to Stockholm with cash (like $45 per person)
  • Stockholm to Oakland nonstop on a cheap Norwegian flight, using the UR portal.

We would arrive early morning in Hong Kong and spend 2 full days. Then we’d have a mostly travel day to Tokyo where we’d spend another 3 full days. We’d then depart late in the evening on an overnight to Doha, where we’d spend a day before continuing on to Helsinki. We’d spend 2.5 days in Helsinki before hopping over to Stockholm for a 2 more full days before returning home. Total of 5 new countries (hmmm…will I get in trouble with China over my classification of Hong Kong?) over 14 days.

a city with many tall buildings

All said and done, it would be maybe $150 per person out of pocket, and the bulk of the long-haul travel would be in a premium cabin. We would be out 150,000 Alaska miles, 135,000 Asia Miles, 36,000 UR (assuming 1.5 cent redemption on a $180 one-way Norwegian ticket per person) and less than $500 cash. Pretty sweet, if you ask me. Some travel would be in business class, but not all of it has to be in a premium cabin (SEE: My first class trip around the world).

What is holding me back?

At this point, the biggest thing holding me back are how I think the kids would do being away from mom for 12-14 days. They have done fairly well the past few trips. Disneyland next week will be another good test. But this would be 3-4 times longer than our longest trip so far. There is also the issue of them being away from their younger brother for that length of time.

The other issue is how comfortable the kids are with new cultures. They have expressed that they enjoy plane travel over car travel, so I am not too worried about that part. What I am worried about is how they’ll do in so many different foreign places over so short a time. Being in the United States has definitely been an adjustment for them, but they have done very well overall. This would be quite a bit different, though.

Finally, the speed of the trip could be an issue. The faster we move, the more likely they will become exhausted, grouchy, and be ready to go home. I know there are steps I can take to mitigate this, but it is a concern.


We’ll see if I decide to follow through on my crazy idea. Spending a month in Europe seemed like a far-fetched idea when I booked it. Looking back, it doesn’t seem so crazy anymore. There is so much of this world left to see, and I want to seize each opportunity to see more.

What do you think of spending two weeks traveling with two kids? Am I honestly crazy to think this is on the table?

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