Rewarding Routes

How We’re Planning Our 2026 Travel Year Using Points & Miles (So You Can Do It Too)

John Diaz Episode 20

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#20 2026 is a year of transition for us, and this episode is about how travel fits into that change. Rather than locking in a packed calendar or chasing big redemptions, this year is about slowing down, planning intentionally and letting travel evolve alongside life.

In this episode, I share a real time look at how I’m thinking about travel during a season where flexibility matters more than ever. Travel isn’t stopping it’s simply taking on a new shape. One that feels more aligned with where we are right now, and one that prioritizes sustainability, confidence and enjoyment over pressure or perfection.

This conversation isn’t about having everything figured out. It’s about learning how to move forward when things feel uncertain, how to make space for change, and how travel can still play an important role even when priorities shift. Instead of focusing on exact plans or rigid timelines, this episode focuses on mindset, decision-making and the thought process behind keeping travel possible during a year of transition.

In this episode, we talk about:

  • Why we’re keeping our 2026 travel plans loose and intentionally simple, and how removing pressure actually makes planning easier and more enjoyable
  • How points and miles become more valuable during years when priorities shift, not as a way to chase luxury, but as a tool for flexibility and peace of mind
  • The mindset change from “maximizing trips” to building confidence through manageable travel, especially during seasons where energy, time, and focus look different
  • How domestic trips help set the foundation for bigger travel later in the year, serving as learning experiences rather than checklists
  • Why planning without pressure can actually lead to better experiences, fewer regrets, and more meaningful memories
  • How this season is shaping the future direction of the podcast, with a stronger focus on learning in real time and sharing the journey honestly

This episode isn’t about exact itineraries or locked-in plans. It’s about the process behind planning travel during change, using points and miles as a flexibility tool, and allowing yourself to learn as you go instead of waiting for the “perfect” moment to start. It’s a reminder that travel doesn’t need to look the same every year to still be meaningful.

If travel feels different for you right now whether because of family, finances, career changes, or life in general this episode is meant to meet you where you are. It’s a reminder that travel doesn’t have to stop when life changes. Sometimes it just needs to adapt, slow down, and take on a new rhythm.

2026 is a learning year.
 Travel will evolve.
 And that’s still a rewarding route.

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#20

[00:00:00] Ever dream of going to Japan, not just once, but every year. Me too. I'm John. And that dream became my mission, which is why I started rewarding routes. A podcast about making Japan travel possible. Year after year, I learned how to leverage credit cards to earn points and miles turning everyday spending into flights and hotel stays across Japan.

Each episode I'll share what I've learned from booking award travel to building meaningful itineraries and deep diving into regions, traditions, and experiences that make this country so special. Let's build your rewarding route one trip at a time. 2026 is going to look a lot different for us. And if you haven't listened to the previous episode, I talk about, um, what I expect, you know, traveling this year will be with our first child .

And, you know, we, we don't want to give up travel. It's something that [00:01:00] we absolutely love. But we know it's going to change and it's going to, um, force us to find like a new rhythm and create new priorities. So in this episode, we're gonna be talking about trips that we have somewhat planned this year.

We're keeping it very loose. Uh, pretty simple. Uh, we have a few trips that are in the works, but nothing has been officially booked yet, but we're extremely excited for this year. I'm also gonna go over the points that I'm starting off with, , here in 2026. So I'll go over all the different programs and points of miles that I currently have, and I'll give a , brief idea of how I plan on using 'em.

We're also gonna go over cards that we plan on opening this year. Uh, things that line up with our goals and, and kinda work for us. And yeah, we're gonna just build on the simple trips that we have planned, build our confidence up, uh, learn how to travel with the [00:02:00] child, and it'll be really exciting,

and we're just, we're ready to meet him. He's still not here yet, um, but he should be here any, moment now, really. It could be either today or maybe another week or so, but. Yeah, he's, it's just right around the corner and we're just, uh, so excited, nervous, and ready to get the year started. So let's get into it.

Uh, what's our mindset for travel this year? What are the things that, you know, we have planned and, um, some things that I've worked towards too. So I've already explained this in a few episodes, but this year I have the companion Pass with Southwest. So that allows me to fly on points that I have quite a few rapid reward, , points, which is Southwest's currency, and I'm allowed to have my wife as my companion.

So basically I'll pay for my flight. She'll be free and all we have to worry about are the taxes for her. And then for the infant, um, we'll figure that out. Um, how [00:03:00] much the lap infant fee is I haven't looked into it 'cause I haven't booked it yet. But once I book these flights, uh, throughout the year, I'll be going over everything that I learned and then we'll be learning together because, you know, point to miles and, and traveling and stuff, there is a lot to learn and it can feel overwhelming, but.

Yeah, we're gonna go through it throughout the year and we're gonna build on this knowledge that we, uh, come across and it'll help me gain more confidence for you, for this podcast, for, for just learning overall and making sure that you get the value also out of this podcast, because, you know, I just wanna provide value first.

Like, I, I want people, I want families to travel, and I know it can be expensive and we can have bucket lists, but it could feel like it's so far away sometimes, and, you know, with this, this economy right now and how, how expensive things are if you could just save some money and, and still experience travel and maybe make it more of a consistent thing in your [00:04:00] life.

That's all I want. So we're gonna move forward and I am going to get into our current points, , going into 2026. So I'm gonna start off with our Chase Ultimate Rewards. Currently together we have 116,544 Chase Ultimate Rewards. Um, I, a big chunk of this was from a signup bonus.

My wife hit earlier last year on one of the, , chase Inc. Business cards. I believe it was the chase. Unlimited, which had like a limited time offer of 90,000 points. And then the rest were just some leftovers. Plus I had accumulated from some spend on some of my Chase cards. So yeah, we have, uh, a decent amount for, you know, those are gonna be used for Hyatts most likely throughout the year.

So yeah, decent amount. We're still gonna try to replenish some of those chase points back, um, just for the following year [00:05:00] and maybe the end of this year. So that's kind of our goal with Chase. Now we'll move on to our Capital One Venture Miles. Uh, this is actually my Venture X, so I have 207,016 venture miles.

This is just something I've had for at least a year, and I use some of it for our. Our previous trip. But yeah, I still had a lot of points left over. So for this year we're, I'm definitely using it for international flight later in the year. Um, it'll be to Japan, so we'll talk about that in a little bit.

But yeah, I'll, I'll use a good chunk of those points , so it'll be good to use 'em for international. , I also have a $300 travel credit that comes with a Venture X. So I plan on using that for some kind of accommodation this year, or rental car. We'll see what I, I need it for.

But yeah, we'll talk more about our, rough draft of trips that are coming this year. [00:06:00] Next we have American Airline Miles and I have 70,920. Now I plan on using these for Japan Airlines flight because, uh, with American Airlines you're able to book Japan Airlines since they're both part of One World Alliance.

So yeah, I plan on using these as well for international flights. I'll use this for like a one way for both of us and, uh, and our child. And then the venture miles, I'll also use for another one way, um, combining those two to create a round trip, uh, using points. So that's kind of my idea behind those two.

Next we have the world of Hyatt. Currently in my account I have 31,501. Now I plan on combining, um, the Chase Ultimate rewards over to Hyatt. So if I combine the points I have over there to my current balance, which is in Hyatt, that'll leave me with 148,045. So yeah, that's a decent [00:07:00] chunk because there are some category eights that I'm eyeing this year, and normally I could find category eight Hyatts for around 40,000 points.

Um, so if I stay two nights, that's 80,000 points. That's, I mean, that's a good chunk of, uh, 148,000. So that's kinda why I am trying , to gain more Hyatt points. And,, we'll be talking about the cards that we're aiming for this year, that, work with our goals and our plans that we have, , lined up next, we have the Southwest Rapid Rewards.

Currently I have 156,048 Rapid Rewards. My wife has 39,434 rapid rewards. I was looking into transferring her points over to my account, but with Southwest, there's a fee to transfer points over to another member. So I looked into it to see how much it would cost to send over her 39,000 rapid rewards to my account.

That way we would just have one pool. But it would cost me about [00:08:00] $390 to do that. So I'm just gonna leave her account alone for now. I'm just gonna book everything through my account since I am the one that has the companion pass and I'm basically just paying for my flights and she's flying for free.

And then we just pay the taxes on top of it, which are normally around $5 and 60 cents I believe. So, yeah, it's not too, not too bad of a deal. I mean, the companion pass with Southwest is incredible and it's probably, it is the best like companion pass out of all the airlines, um, in the industry right now.

So I'm extremely happy I have that, that way it makes. You know, 156,000 points. It, it'll last us all year, uh, for some domestic trips that we have planned, plus positioning flights getting from the East coast in Orlando over to the west coast. That way we can take a West coast flight over to Japan and I should have some leftover for the following year.

What I am planning on doing is maybe in 2027 I'll have cast. [00:09:00] Apply for another Southwest card. She did have the priority card, but we went ahead and canceled that card because she wasn't really, um, she wasn't really needing it for this year, , since I had the companion pass and they just raised the annual fee on the priority.

So I, we didn't want to pay the annual fee for this year. It didn't make sense for us. But in 2027, we will look more into the options with Southwest cards because. You know now with Southwest not being like open seating, you get to pick your seats with the credit cards. And also check in free luggage and some other benefits that we have to look into, but.

Yeah, that's kind of our plan for, uh, 2027 with Southwest. But yeah, I'm gonna cover, um, all of our flights for this year using the Companion Pass. Now moving on to Built. And currently I only have 17,028 built rewards. , Not too many. , I was using it for rent for the past couple years. , [00:10:00] We. Left our apartment, , during, I believe August of , , 2025, and we just moved into a home.

So now we have a mortgage and I'm actually really excited, , that, , built has come out with a 2.0 that, you know, covers mortgages and rent. But I'm going to make an episode all about the built 2.0, getting more into it, seeing if it makes sense for me and if it makes sense for you, because I'll be going over the details.

, It just came out yesterday, the details, and I can tell you that it's very, they came out with a very complex, , system, and it's going to take me a little bit to wrap my head around. Just so I have all my details figured out, and I understand the system myself before I explain it to you, but yeah.

, Built definitely didn't make it easy to understand some of , the new changes, especially paying mortgage and rent. It's something that was, I mean, a no brainer for, for most people. Like a no [00:11:00] annual fee that that covers rent. And you can, you know, get points off of one of your largest expenses. But it's not like that anymore.

It is like that. But there are, there are ways, there are, there are ways around it, which are the complicated part. So, yeah, we'll get into it in another episode. And now that'll take me to cards we're eyeing for this year, and the first card I'm eyeing this year is the new built cards that, you know, was, was just announced yesterday and.

The one that sticks out to me is De Palladium. De Palladium is the highest tier for Bill. It's a 4 95 annual fee, but it does come with a priority pass, which would be nice to have this year. Um, the only reason I say that because my Venture X has priority Pass, but as of February 1st, the priority pass and the lounge access for Capital One lounges.

Is only for the card holder, which would be just for me [00:12:00] and my wife, and my child wouldn't be able to go into the lounge unless I pay a fee, which I don't want to pay a fee. So that's why this built card on the built Palladium is, I'm interested in it. The thing is there's wording with this card that I'll get into in the, in the next episode, but it, it just throws me off and.

I don't know if this card is for me. I'm not sure if it lines up with our goals, so we'll see because there's some credits with it that kind of pay off the annual fee in some way. But you had the wording that comes with it. Just, I don't know. I have to think more about it and I have to see how the um, bill.

Cash Works because built Cash is now separate from Built Rewards. So you basically earn points with built, but you also get cash back with built cash, and that's used in a different system within like the built ecosystem. And yeah, I'll get more into it. It's a little bit complicated. But it's an interesting card.

[00:13:00] And Built has some of the, or if not the best transfer partners in the market right now. Some examples are Hyatt, Alaska, and Japan. Airlines, like these are main targets for myself. Um, hi. It's going to cover the accommodation. Alaskan can get me over to, uh, Asia, either on Star Luck, over to Taipei, or I could take Japan Airlines with, um, Alaska, since they're both one world partners.

But Japan Airlines is also a transfer partner for Bill. Currently, you can only transfer from built. To Japan Airlines or Capital One. But Capital One doesn't have a one-to-one ratio like Bill does. So with Bill, it's like a thousand points. With a thousand bill points would equal a thousand Japan airline miles.

But with Capital One, it's only a thousand. Capital one miles would be 750. Japan Airline miles. So you're not getting the full value with the Capital One transfer, but you are getting the full value with [00:14:00] built going over to Japan Airlines. So yeah, I mean there are so many other great transfer partners for built that, I mean, make it the best in the market right now.

So that's another reason these built cards and especially the Built Palladium has my interest. I just have to do a little bit more digging to make sure it makes sense for me. And this is. A good example. Whenever you're looking at a card, always do the research and always make sure that it makes sense for you.

The signup bonus on it makes sense for you and to spend some cards can be a little bit couponing with like giving you multiple credits to use on multiple things. But the thing is the credits don't always make sense for you.

So always do your research when you're looking at new cars. Make sure that it aligns with your goals. And that's what I'm having to do here and I'm gonna go over my whole thought process in that built episode. Now another card we're looking at is another Chase Ink business card. And [00:15:00] this is to help replenish those Hyatt points that, you know, we're always seeking for.

, My wife doesn't have the ink preferred. She has the ink cash and the ink unlimited. The ink preferred has the $95 annual fee, but it normally comes with a pretty nice signup bonus, which is around 90,000 points. , The only thing is Chase has changed its rules and wording around its cards, and they've also been a little bit stricter on approval.

So this isn't a sure thing for us. , She would be okay getting the ink preferred because she's never opened the ink preferred before, but I was going to try and get the ink cash. The only problem is I have a Ink unlimited and now that they changed their rules. Their rules kind of state that if you already have a no annual fee ink card, then you wouldn't get the signup bonus if you applied for another no annual fee ink card

so technically by the [00:16:00] wording, they don't have to give me to sign a bonus for the, the cash ink card since I already have the unlimited. Sorry if that was a little confusing, but. Yeah, that's, the situation I'm in. I'm still going to try to get the ink cash, but normally there's a popup that comes up saying you're not eligible for the signup bonus.

I'm kind of expecting it, but we'll see how it goes. 'cause I know some people are still able to get through even though they have like another ink or, , limited or cash. So, yeah, I mean, I'll give it a go and I'll let you know how it goes. , I realized I haven't made an episode about business cards yet, and it's actually, , a strategy that we use.

It's really easy and it just got me thinking I should have an episode about that soon. So, , if you're a little confused by the ink, like business cards and why it's a strategy for us, I'll be making an episode about business cards, kind of going through it and, , why they're.

A really valuable asset to, , points of Miles. Now next [00:17:00] card we're looking at is the world of Hyatt cards. Once again, we're trying to build those Hyatt points up. We both don't have either of the personal Hyatt cards or the business Hyatt cards. The reason I haven't opened this up, and I was going to open it up last year, is because there are rumors of a new Hyatt card coming this year, and it's maybe earlier this year, hopefully spring.

So with a new card, and sometimes what I realize with new cards, they, they come out with like, uh, limited time offers. So it'll be like a boosted signup bonus. So I'm kind of just holding off on opening up a Hyatt card and see if the more rumors come out. And maybe Hyatt does come out with a brand new card this year or so.

The chances I think are very likely to happen, and that's a card that we'll definitely get on. Now, the last card we're gonna go for are any limited time offers that we find. So these are [00:18:00] cards that, you know, run special offers throughout the year. If we find one that we really like that fits our goals, we'll be going for it.

, So I'm just going to keep an eye out to see if anything drops throughout the year that is like, wow. Yeah, that's a great signup bonus. That card makes sense for us. Let's get it. Currently we're both at three and 24 for like, chase's, like three accounts opened in 24 months, two years. , In March we dropped a two in 24.

So we have room to open up more personal cards, and it's usually pretty good to be under, uh, five and 24 in case one of those cards are a Chase issued card. That way you'll get a, well, hopefully you'll get approved for it because if you're at five and 24 or over, you're gonna get denied by Chase most likely.

So that's our, uh, strategy going into this year with cards. What we expect to get. And hopefully there are great limited time offers that come out. And of [00:19:00] course, with every card, with every trip, I'm gonna go over it in, uh, in future episodes. Now, let's get into what our travel year looks like right now.

Right now we don't really have anything planned until the summer. . Nothing officially booked yet, but in the summer we plan on going to Chicago. , My wife has some family, , over in Illinois, but yeah, we want to use the companion pass plenty of nonstop flights with Southwest, from Orlando to Midway and O'Hare, so we have options there for the companion pass.

This will also be our child's first flight, so. You know, I think it'll be a good test. It'll give us an idea of how it goes. It'll get us more comfortable, you know, build a confidence, see what works, what doesn't. We'll also be staying at a Hyatt in Chicago. The one I'm eyeing right now is Chicago Athletic Association.

It's right next to. Millennium Park, , not far from the Art Institute of Chicago. I mean, I've been, we've been to that park already and we've [00:20:00] been to Chicago a few times, but, um, this will be her first time with a child, of course. And I don't know, I think it'll be nice to be around that area and take walks around the park and, you know, grant Park is really big and, , we'll also be going to a museum, the field Museum because, , Pokemon will be hosting from.

May of 2026 to April, 2027, like a Pokemon Fossil exhibit. So that'll be cool to, to be able to experience that and experience the field museum. I don't think either of us have been to the Field Museum, but we have been to the Art Institute that we really liked as well. So it'll be a great trip. I think it'll be a, a good learning lesson and just a fun like summer trip to take together.

Now, also in the summer, we plan on going to, . South Florida over to Fort Lauderdale. There's actually a convention going on down there, and, , pat Flynn is the host of it, and Pat Flynn is, , someone that's very inspiring to myself. And he wrote a book that I read last year called Lean [00:21:00] Learning. And, , it's a big reason that I have this podcast going right now.

It's the reason why he started. , So I would like to, , meet Pat Flynn, but also have like a nice beach downtime kind of trip just to, to relax and hang out by the beach. So I'll be using some high points for a stay over by the convention center over there in Fort Lauderdale. Um, maybe we will adjust a trip to maybe stay in Miami.

If not, I'll be driving down there since we're only a few hours away. But I think it'll be a, a really fun trip and, you know, we get some beach time with the baby, so yeah, it'll be good. Next we have the Japan trip for fall that I'm trying to plan, , sometime in November. This is the big one for the year.

I think we only have one international trip this year and it's gonna be Japan. Uh, location's gonna be to be determined. At the moment, we wanted to do QU and kinda stay in Fukuoka and make our way around Qsu, but. We will see [00:22:00] what we'd end up doing. Um, I do wanna reach out to some people who've traveled with, uh, like a one yearold or, or just under a one yearold and, and see what kind of itinerary they built out and what worked for them, what didn't.

, Just so it can help us base on what kind of trip we wanna try to do. , We know we wanna keep it simple and we're gonna go slow and keep it, you know, slow paced overall, but. Yeah, I don't, I don't completely know where we're gonna go for this trip to Japan. Um one thing I would really like to do is to check out the , Nintendo Museum over in uji, which is right, like right next to Kyoto.

Really not too far of a train ride from, Kyoto. But yeah, we'll see. We'll see what kind of trip we take. Maybe we will just enjoy the Mount Fuji area as well as something I was thinking about. Getting like a Rio Con over there with a private onsen and just relaxing, just taking our time, just driving around, um, mountain Fuji [00:23:00] and, and just soaking in that area.

So that's another idea. Um, we'll see, we'll see what we end up doing and we, we end up planning, of course, once these plans become more concrete, I'll share those on this podcast and, and give you guys the full itinerary and, and what I've come up with from there. But yeah. With this Japan trip, we'll be using, uh, the Southwest companion Pass to position ourselves from the East Coast to the West Coast.

Of course, I'll be using Hyatt points. I'll be using the venture miles for the flights from the west coast of Japan, and then I'll use those, uh, American airline miles for Japan Airlines flight. . Probably coming back or going there, whatever works best. I'll play around with it, but it's going to be really exciting planning this trip, and I hope I get to reach out to a few people that have done this kind of trip, especially with, , under 1-year-old and see what.

Their itinerary and their experiences was like, so, you know, I'm, I'm hoping to reach out to them. Either I just chat through [00:24:00] Messenger or something, or I could hopefully bring them on the podcast and we can have a chat and uh, talk about it here and have a conversation. That way you guys can hear as well.

It's something that I really want to bring to this podcast, bring interviews over and, and have conversations that way. We can hear from other perspectives and people that have either used points of miles or have traveled with a child or, you know, maybe who even live in Japan and, and what's their experience out there and like, how are the different prefectures and the different things to do that aren't just the golden route of Tokyo, Kyoto, Osaka.

And we can expand, we can expand a podcast and we can enjoy these conversations and learn from them. So that's something I, I would love to build here in 2026. And that's a goal of mine is to bring some interviews over, , to really bring those conversations to life. And, and it's really exciting and I can't wait to bring that to this podcast.

[00:25:00] So let's go to over to the next trip. And that next trip will, I would like to do a cabin trip. . Most likely, it'll probably be somewhere in Georgia. This will be closer to the end of the year. I'm planning on using the venture travel credit that I'm giving of the $300. On a cabin somewhere in Georgia, or maybe it's somewhere a little bit up north.

We'll see, but , we do want to be out more in nature and it's something we haven't done the past year or maybe like two years. So maybe visit a national park and stay at a cabin at National Park or just find like a. A really nice area that have cabins. Uh, a place that comes to mind is maybe Blue Ridge.

The last time I was in Blue Ridge was for a bachelor party of, uh, one of my best friends and I really enjoyed Blue Ridge, Georgia, and it was beautiful and we stayed at a beautiful cabin out there. So I would love to have that trip for us. And to be out in nature and, and [00:26:00] just soak that in and yeah, I think that'll be a great way to end 2026.

So overall, that's kind of where we are right now with our trips and what we have planned. Of course, we can add maybe a few more in there, smaller trips or. Or maybe just keep it like that and keep it simple. , Yeah, we have the big international and then some others, but with the companion pass, I would like to use it a little bit more than that since I have it for this year.

So maybe we'll do some, we'll maybe we'll do some more domestic trips throughout the year and we'll just sprinkle those in. , Maybe like one nighters or two nighters, so like very short. , To cities maybe we haven't been to or maybe cities that we want to explore again, that we have been to. So we'll see.

We will, we'll go over it as that time comes, but. I think, , the big takeaway from this episode is, you know, you don't need to stop traveling when life changes, you know, with a child on the way. , Yes, it's a, a nervous feeling and it's scary, [00:27:00] but, , I know these changes will just have to make adjustments to them to make it happen.

And points and miles really make this all possible for us. Like we wouldn't be able to travel. Maybe do one trip this year instead of multiple trips, but because of points of Miles, it allows us to do multiple trips , and they're simple trips, but we're able to still get out and travel , and explore new cities , and experience new things together.

So, , this is the real value of points and Miles being able to let us consistently travel throughout the year and experience, , travel with a child of ours and. I hope you can do the same. You can travel and you can experience so many different places and not just do one trip, but do multiple trips throughout the year.

So I'm really excited to hear what your trips are like or are planned for 2026. Like if you have any great trips coming up. If you're using points Miles, definitely reach out because [00:28:00] I've actually had a message about somebody that just hit a signup bonus on a Chase Sapphire preferred. And they're excited to go out to Europe.

So I'm stoked to see that kind of message, , come in. And even though I just cover Japan and using points and miles, you can take this concept and go anywhere in the world that you know is on your bucket list. And this is what excites me. This is what it's all about for me. You know, to travel more, to travel more affordably and more consistently.

I, I hope you enjoyed this episode. Let me know what trips you have planned in 2026. Let me know what cards you may be targeting. If you have any questions, always feel free to reach out. I'd love to answer any questions you have. And yeah, that'll wrap it up now and I'll see you on the next episode. See you.

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