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Theorycrafting miles and points travel with three kids

I have a colleague who cites travel as one of the reasons for not having a second child. I totally get it, the more kids you have, the more difficult travel becomes. So, truth be told, travel was one of the major considerations on my mind before we went for three. What will travel with three kids look like? 

So, this post contains the travel complications I considered that a third child might create. I won’t say that these concerns would ever have prevented us from going for it, but I definitely paused to think. Ultimately, we decided that we’d having a third child was more important to us than keeping our travel lives at status quo – the last two weeks have only made me feel more confident about that! 

After each complication, I’ve also theorycrafted a bit about how to deal with these complications. Obviously experience trumps theory, so if you travel with three kids (or more!) and want to share tips, I’m all ears in the comments. Thanks!

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Concern 1: Cost of air travel with three kids

Cost of air travel (and travel in general) tops the list of most family’s concerns. And obviously we’re a travel hacking family that doesn’t really pay for flights with cash. I’ve learned I don’t even need to pay for Disney World with cash!). Still, since we eventually need to procure tickets for five people, even I’m beginning to worry about budget. 

We happily have met our goal of taking 2-3 domestic vacations and one big international vacation ever year even since we had our first child. I basically earn enough points through credit card sign up bonuses and some light MS to cover the cost of all these flights.

However, our last trip to Hong Kong DID cost 420,000 miles – that was only three tickets in Cathay Pacific business class. That same trip, without devalutions (no guarantee), in two years will cost 700,000 miles!

Are you a large family preparing to travel with three kids? There's a lot to worry about, from cost to logics. Here are ideas to deal with the added stress!
I am seeing a lot more Jetblue in our futures
Theorycrafting solutions for cost of air travel

My goal remains unchanged – two or three domestic trips and one big international trip per year. Since I want the kids to get to Hong Kong or Taiwan (preferably both) every couple of years, here are my plans for how to make it happen.

1 – Hoard more: it’s going to be impossible to fly in business class if I don’t hoard more miles

2 – Fly one way in coach for European vacations if necessary: I really want that business class when we go to Asia and will save miles to Europe if need be. Those flights are pretty short, like flying to California, anyway.

3 – Take more road trips. This should save me some miles in the long run.

4 – MS a little more. Honestly, with 3 kids, I barely have the time, but if I need to, I can do this in a pinch to top off accounts.

5 – Lean on cash equivalents like US Bank Flexperks for domestic travel. This should save my transferable miles for the big redemptions!

Concern 2: Hotel room occupancy for travel with three kids

If you follow me on Twitter, you know I got slightly involved in the Deal Mommy and Pizza in Motion’s “spat” about hotel status. In their discussions they hit on one of my major travel concerns about a third child, hotel room occupancy. I used to maintain Hyatt Diamond (now Globalist status) for the confirmed suite upgrades.

I found, however, that both the Hyatt Regency Tsim Sha Tsui in Hong Kong and the Hyatt Regency the Churchill base level suites have a room occupancy limit of 3. So I had to lie/talk my way into those suites when we were a family of four, I imagine things will just get worse now. 

Are you a large family preparing to travel with three kids? There's a lot to worry about, from cost to logics. Here are ideas to deal with the added stress!
Believe it or not, this Hyatt Regency suite at The Churchill in London has an occupancy of 3. We had to ask the manager special permission for four of us to stay there
Theorycrafting solutions for hotel room occupancy

1 – Look to apartment rentals/AirBnB more. We already have moved in this direction since having a kitchen is indispensable for young kids, I expect us to move further in this direction

2 – Earn more cash back. (To pay for #1)

3 – Book adjoining rooms more often. This will especially work at low category hotels with cheap redemption costs

4 – Bring the grandparents and “assign” one of the kids to their room

5 – Contact hotels in advance to explain our situation and try to get a room that works for us (or leniency on occupancy). The worst they can say is no!

Concern 3: Uncontrollable chaos 

“You get to play zone defense now.” I’m not sure how many times I’ve heard that since we started telling people we were expecting our third child. Even more people say it now post birth. Well, in my limited understanding of sports, zone defense usually means you just leave one person wide open.

Travel with kids can be chaotic, travel with three kids could very well be a nightmare. When they’re young, you’ve got conflicting nap times/schedules/interests. When they’re teenagers, you probably just have conflict!

Theorycrafting solutions for uncontrollable chaos

1 – Bring grandparents.

2 – Survive.

Honestly, I’m not sure what you can do about this. Chaos is chaos, and personally I don’t mind it. I know travel will be chaotic (it already is!), but despite the chaos we still find family travel incredibly rewarding. So I’m not gonna sweat this one TOO much.

Are you a large family preparing to travel with three kids? There's a lot to worry about, from cost to logics. Here are ideas to deal with the added stress!
It happens.

Concern 4: Length of travel and locations for travel with three kids

One of the very few things I miss about not having children is the ability to get away for long, or even short, weekends. With miles and points plus the litany of fare sales, we used to be able to get away to Europe for a long weekend. Three kids and a dog has made that near impossible. And while it’s possible to take a child for a solo trip, we probably can’t take long weekend trips until the kids are older.

We also need to be picky about locations now. If we want to use miles and points to book hotels, Hyatt usually is easiest but they have the smallest footprint. Apartments often allow us to stay put in one place for one week, which helps with travel stress and also gives us the chance to really get to know a location.

Are you a large family preparing to travel with three kids? There's a lot to worry about, from cost to logics. Here are ideas to deal with the added stress!
We loved our long weekend in Lyon, but that won’t happen again for the foreseeable future
Theorycrafting solutions for length of travel and locations

1 – Focus short weekend trips on domestic road trips or destinations less than three hours away, preferably avoiding time changes of greater than one hour.

2 – Even overseas, look for apartments where we can stay for a good amount of time

3 – To pay for 2, invest more in cash back

4 – When switching time zones for international travel, stay in that time zone as long as possible to make the most out of the up front jet lag pain

Concern 5: Health 

One thing we thought of before going for our third and one thing we think about all the time is health on the road. Obviously, the fear of something medically happening on the road never deters us but with three kids the odds of a sick child increase exponentially. 

Then, of course, after we conceived there was a point where I was worried we might not get to travel at all. Until she was born, I wasn’t 100% sure what needs CC might have and whether they might preclude us from almost all travel. Going into the third child, I definitely already accepted that our family travel would never be the same again. But with the health curveball, I spent a good couple weeks wrestling with the possibility that we might not have any family travel at all anymore. 

Are you a large family preparing to travel with three kids? There's a lot to worry about, from cost to logics. Here are ideas to deal with the added stress!
Sleeping off a fever in London

During that time, I came to two conclusions, one sort of trivial, one kind of deep.

My trivial conclusion, I kid you not, was that no matter what we were dealing with, I knew we could still take the family to Disney World. I know that probably sounds crazy to people who could not care less about Disney, such as my wife. But Disney World remains one of my favorite places to visit, and I’ve seen first hand how well Disney deals with kids with special needs. Yes, Disney at the end of the day is a corporation, but the ground level cast members dealing with kids with special needs are simply spectacular. I found comfort in the fact that my family could still take that particular trip no matter what.

My deeper conclusion was more of a reminder. I love traveling and I love traveling with my family. The prospect of possibly losing that hurt. Of course, my family itself is more important than travel, but it took the possible loss to remind me how much I love travel itself. (For the record, it was a risk I was willing to take to have a third child). 

Thankfully, everything worked out well enough that our travel shouldn’t be greatly affected (if at all). But I appreciate our chance to travel more than ever now. 

Theorycrafting solutions for health issues while traveling

1 – Make sure we pack all necessary medications including children’s tylenol, benadryl, bandaids, etc.

2 – Have a general idea of where to go for medical help if necessary wherever we go

Final Thoughts

Sorry to get a bit deep at the end there, guess I’m still processing. Overall, I feel like we’ve mentally prepared as much as we can for travel with three kids. Now, it’s time to do it! Since we’ve mostly got all the medical stuff squared away, I’m looking forward to planning my trips as these miles and points burn a hole through my pocket.

Like I said up top, if you are a family of five or more, I’d love to hear your tips for traveling in a four person family tailored world. Miles and points tips, general travel tips, I’m all ears, hit me up in the comments!

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Are you a large family preparing to travel with three kids? There's a lot to worry about, from cost to logics. Here are ideas to deal with the added stress!


Just an average joe trying to fly his family for less

8 thoughts on “Theorycrafting miles and points travel with three kids

  1. Love this. And yes, you are right: more air tickets and running into occupancy problems for sure. My solutions have been the same, making sure an annual road trip happens and having flexible points options to find a hotel that will fit us without advance negotiation. Chains that work for us are Hyatt Place, Springhill Suites, Residence Inn, Staybridge Suites, and some independents in travel portals.

    And, I’m shifting from wanting points-paid air and hotel, to just wanting to offset it all as much as possible and keep our daily average expenses below a certain threshold.

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