Traveling With Kids on Points & Miles: Our Top Family Travel Tips

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What's the kind of framework that you go through when, when planning travel? You know, walk us through how you typically start planning a trip, deciding on options, the flexibility, must-haves, nice-to-haves.

Just like what's that thought process like for you?

Yeah, sure.

So, uh, typically I'm usually working within the confines of a timeframe.

Um, you know, my kids do traditional school, so we're not homeschooling or anything like that.

Uh, I've got, you know, kids in travel baseball, which if anybody else out there knows, like it's incredibly time-consuming.

So I work...

You know, I kinda have to look at the time periods, periods I have available and then work backwards from there.

So a lot of times I don't have a specific destination in mind.

I'm like, you know, okay, so, you know, I know a couple of the things we're gonna talk about are over spring break.

I'm like, "Okay, I have this week to work with." Um, it's very hard for me to say, "I'm just gonna go here." I usually just look at that timeframe and then kinda do some searches and see what's available.

[laughs] Like what, what-

Yeah

... can I do with my points, you know, for the least amount of points, but also, you know, the most convenient route too.

Because if I've only got a week, it's not like I can, you know, go to Southeast Asia, for instance.

I need more time.

So being in Florida, I'm kinda lucky in that respect.

We're so close to the Caribbean and Central America and some different places.

That way I, you know, I can say, "Okay, let me look at this whole general area and see where I can find the best flight." And then usually once I find the flight, then I kinda work backwards and say, "Okay, now what am I gonna do in this place?" And work-

Yeah [laughs]

And [laughs] that all comes together.

Yeah.

Yeah.

S- s- so it sounds like it's less of kinda getting your heart set on a destination, trying to make that place happen, and just being open-