Rich Girl Roundup: Our Best Travel Tips, Maximizing Points, & Early Bookings

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There are so many benefits to booking travel in advance: psychologically, logistically, and financially. What's the best way to do so, and how can we book our travel to get the best bang for our buck?

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Transcript

Transcript

Katie:

Welcome back Rich Girls and Boys to the Rich Girl Roundup weekly discussion of The Money with Katie Show where we get the opportunity to more casually dig in to some interesting money questions from our community. Here's a quick message from our sponsors

Before we get into it. This week's upcoming main episode is about defining what is enough for you. So it's not just an exploration of money and what income limit or financial independence number feels good, but it's also about redefining how we tend to move the goalpost once we unlock new achievements or milestones, the way that things usually continue to creep upward. And we often have kind of a hard time experiencing true contentment. So I think it's going to be a nice mix. Alright, Henah, onto the roundup. How are we doing? What is this week's question?

Henah:

I'm good. I have a question for you. Do you have any travel plans soon?

Katie:

I just got back from Colorado, which is a family tradition for Thanksgiving. But no, I actually don't have any travel plans right now.

Henah:

Well, you and this listener can get all the tips at once. So this week's question came from deep. How far in advance should I plan my travel in order to optimize it the most? And I would assume that you're talking about those one to two per year type trips. Katie, what is your best practice on booking your travel for in advance?

Katie:

Oh, well I used to work for an airline, so I feel like I'm kind of in the know a little bit on some of those tips, but I did some digging just to confirm that my intel was still accurate. And generally speaking, for domestic flights, I think they say recommended to book one to four months in advance. They say that the sweet spot typically is between 30 to 90 days before departure. Some sources were like 76 days. I don't know if I really buy that. I think it depends on the airline and how their revenue strategy teams are doing the pricing. But that was what I found. So I thought that was kind of interesting.

And then for international flights it was saying that six to 10 months before the travel date is often best, which I thought was kind of interesting. It sounds like people are kind of suggesting you give yourself that really long window so you can use those flexible rate calendars and see what times are looking good and off peak, but that there is some flexibility with the booking itself. So I don't know. I think generally I'd say begin monitoring prices as early as possible. If you know you want to go somewhere and you can set the price alerts on Google flights and whatnot, but I don't know, this is something that I have not usually been, I would say as optimized as I could be.

Henah:

This is my bread and butter, Katie, so get ready for my sermon.

Katie:

I’m ready. Okay, go ahead.

Henah:

So if you're paying cash, I think Google Flights function is fantastic. I think they also introduced a new price match option, which is really exciting. So you can subscribe to fair alerts and drops if they happen, but I do think kind of a year out can be a sweet spot if you know also because that's usually when the flights you can or do with points will book up. So that's something to keep in mind.

Google Flights also has that little bar at the bottom that shows you what an ideal price is or a good price. So you can kind of use that as your measure of this would be the ideal price. And this is where I feel okay and comfortable paying. But something I learned from my friend who is a travel agent, which I'll talk about a little later, is she actually said, most US airlines now allow you to get a residual voucher if when you book a flight the price leader goes down so there's less risk in booking, which is really comforting.

I think the only caveat she said is that it's not applicable to basic economy, so it's just something to keep in mind. But I know for example, my husband and I want to go to Italy next spring, so I've been checking out the cash rates on those. But I also like the extended timeline because it lets me leverage points a little bit more strategically. So I've been checking out transfer deals on the Amex card and Bilt and Chase for airlines that go to Rome and seeing if any of those are worthwhile. So a very niche tip for people who like going to Europe a lot, KLM has a Flying Blue promo every single month where they'll drop these incredible round trip flights on points deals. And so we've booked that in the past before to go to Europe for 20,000 points, a person round trip, which is a really nice use to stretch out your points. Do you have any other tips on redeeming via points or kind of molding how you build your trip that way?

Katie:

I think generally the process that I like to follow is to always start with Google Flights because it shows me what carriers I should even be looking at. So if I know I'm trying to go from Denver to Denmark, I know that really the only option I'm really going to have is United, but that I can use United Partners to book that flight. So what I would probably do is use the Google flights to identify which flight in the flight schedule and which carrier am I actually trying to get on. And then which partners based on those, I think it's like Star Alliance or you mentioned Flying Blue I think…

Henah:

Like One World.

Katie:

Yeah, yeah, yeah. I can't remember the exact name of what those partnerships are called, but where you can book these flights are marketed on different airlines based on the connections and partnerships that they have. I would probably then go, okay, what is the most efficient way to get that specific type of point? So maybe if it's United, then you're looking at both the United Card, you're also potentially looking at Chase cards because those can be transferred to United. How can you cobble together, especially if it's going to be many thousands of dollars and you're in the market for a new credit card anyway. If you have that much runway, pun intended, like six to 12 months of time that you're planning, you could easily basically just stack a signup bonus or two and probably cover most if not all of that expense. So that's something that I would probably do if I had a big trip planned where I knew in advance I want to pay for this with points, so I'm going to go out and structure my credit card strategy around it.

Henah:

There's a little tool sometimes I'll use, it's called Point Me, point.me is their website and it will read through all of the different credit card options that you can use for points like 35 different programs or something like that. And you can get a free trial where you can look at three different trips in one day or three different redemptions in one day. And then I think you can pay $5 for one day of use where if you know what you're planning for, it's a very easy way to be like, okay, it'll show me that I need 45,000 points to book this. Here are the three programs that'll get me that, but Amex has a one to three redemption rate for this, so maybe use that one.

And then as far as hotels and accommodations, I use a similar approach with chains like Marriott or Hilton or Hyatt. But I think one thing that I approach a little bit differently for hotels is how will I save the money for the hotels themselves if I know I want to stay at a nicer place and points are not an option. So for example, my husband and I are going to the Philippines next month and we were like, oh, we can stay at the Shangri La in Manila, and then they had the fine hotel and resorts credit and then we could use some points and I was like, cool.

Katie:

Which is an Amex benefit, for anyone that's like, what is that?

Henah:

Which gives you I think $200 of credit a year to use towards that. So we ended up getting It's

Katie:

Per trip.

Henah:

Per trip?

Katie:

It's $200 per trip.

Henah:

Oh, I thought it was annually for the whole year.

Katie:

Oh, well there's the hotel credit, which is $200 off once.

Henah:

Yes, that's what I was referring to.

Katie:

But then if you use the fine hotels and resorts, you also get $75 per day breakfast allowance and a $100 resort credit. So sorry, that's what I thought you were referencing was because it was in that category.

Henah:

So we ended up booking three nights at the Shangri La for 400 bucks for two of us. So I was like, cool. That's a great redemption for me.

And then sometimes I'll also ask, are there other deals and promos I can leverage for extra points when I book in advance? So if you have that long runway, you might see, so for example, with Expedia last week they were doing a promo for 11% cash back. So I was like, cool, I have a lot of time, but I know where I want to go. And then Amex obviously has this and Chase as well has those cashback offers. So that's another thing that I try to think about that could impact where and how I book. And then the last thing I try to ask myself is the layout of my trip. Will I want to splurge after traveling for 30 hours? Probably so. And so that kind of big picture approach for me lets me look at the availability of everything and be like, well, I have six months to decide what I'm going to book, but now I can keep an eye out for, I know that on this date I'm going to want the nicer hotel and on this date I don't really care. Do you have any hotel hacks that you use?

Katie:

Typically we do the Bonvoy thing because we just have been able to rack up a lot of Bonvoy points, and I think they do the fifth night free if you're a member. I can't remember what the exact, it's like if you're booking a five night trip, your fifth night will be free, which then kind of lowers the cost per night average. So I like Bonvoy for that reason. I also think that the Hyatt properties are often really solid redemption values. I know when we had, was it Benet Wilson that came on the show, she had talked to us about, I think she really likes Hyatt Properties and I agree, I think you can get a really good redemption value with Hyatt. And so that's another one where Chase points being used converted to Hyatt points. It's pretty much the only hotel program that makes sense to transfer Chase points to. But depending on the redemption value, you can get some really good redemptions there.

Henah:

I think I've only ever redeemed Hilton. I have to start a new Hyatt strategy. And then in terms of intercountry or intercity transportation, I tend to book that out one to two months in advance.

Katie:

Oh wow. Which

Henah:

Might seem like overkill, but I do find that a lot of times it's either sold out or there's strikes happening, especially for a lot of European visits. I try to just be mindful. So

Katie:

Are you talking trains,

Henah:

Trains, buses, ferries? You

Katie:

Can book buses two months in advance?

Henah:

Yeah.

Katie:

Oh. Wow.

Henah:

I did that for the trip that I'm on right now and this goes live. Yeah, so we interesting usually do that and sometimes it's just a month out, but just knowing that I have the ticket in my hand and I'm not worried about something being sold out gives me a lot of peace of mind. But I do have a little hack that I mentioned before, which is the value of a good travel agent. So my very good friend is a travel agent. She was able to do our honeymoon and they work for free for you, but they get their commissions from the actual vendors that you book. So you give them your budget, your timeline, they have your best interest in mind of what you want to be doing. And I just got so many incredible opportunities from her that I could not have DIYed myself. We got that Overwater bungalow in Bora Bora that I could not have gotten had. We just booked it on our own and we didn't pay for it, which was incredible. So

Katie:

Do you have any recommendations for it? This is your close friend, but if someone doesn't have a friend who's a travel agent, do you have any recommendations for how to find one?

Henah:

I would say honestly, you can go by word of mouth. I mean, I'm happy to recommend mine. She's incredible. I think having a really knowledgeable person who knows the deals worldwide is very important. There are some who are very specific to Disney resorts or some who are like, I'm a European travel agent. So it really depends on what you're looking for in that sense. But word of mouth I would say is the biggest one. There's some groups on Facebook, like Travel Community or I believe Scott's Cheap Flights or the Points Guy, they have their own travel community on Facebook. There's some people on there who are always asking, do you have a recommendation? I'm sorry, I don't have a better answer there.

Katie:

No, that's great. I was just curious if there was any, because I know you're in some of those Facebook groups, so I was curious if you're like, oh yeah, there's this whatever resource that people can use, but that makes sense. I

Henah:

Have seen in Conde Nast Traveler Magazine and stuff, sometimes they'll have some really incredible travel agents, but those are luxury. Like you're paying for a $15,000, $20,000 trip. So wow. Can't say I relate to those people.

Katie:

That’s a lot.

Henah:

I wanted to add, when you're planning a trip in advance and you see a really good flight deal is you have to ask yourself, is there a flight deal on purpose at this time? Is there a reason why it's so cheap? Sometimes you can look it up and then be like, the weather that time of year is horrible. That's why this is so cheap. Or it's an unusually expensive time to go because there's a festival. So they're giving flight deals to people who want to go, but then you're going to eat up all of the other cost savings that you saved on the trip by booking a hotel that's three times the price. So I do think that you want to consider that as well if it's too good to be true. It probably is.

Katie:

When I worked at Southwest, there was this thing, it was like the Easter egg of the airline industry. It's called an error fare. Oh yeah. Error as an E-R-R-O-R, error fare, FARE, where sometimes airlines will accidentally publish the wrong number for a cost. And so I had friends that, I think they went to Tahiti for like $15.

Henah:

I did a mistake fair in 2014, $179 from New York to Milan, Prague, and Amsterdam, $180.

Katie:

Wait, how did you go to all three places?

Henah:

You could book all of the fights in one go. So I had to just, was it

Katie:

Like a skip lag thing?

Henah:

No, it was literally just a mistake. Fair that they ended up honoring, I don't even know. There was no way to come back. You had to book the way back on your own, but it was like 300 bucks or something. So I was like, sure, I'll do $180. That was my best mistake fare ever.

Katie:

I don't think there's really a strategy for finding them. It's just kind of a fun thing to know that they exist and they're out there and usually I think if memory serves the domestic airlines release their fares on Tuesdays. I think that's when new fares get filed on the backend.

Henah:

The one thing to be mindful of with mistake fares is definitely making sure that they honor the fare and don't start booking things right away once you find one, because they might cancel it on because I've had that happen to my friends. But remember too that when you're booking a flight, at least in the US, you do have the first 24 hours to cancel and get a full refund, which is sometimes nice. If you see something, you do see a deal and then you're like, okay, I have nothing to lose. Okay. Me booking things and then going to Katie and saying, can I have this time off? I've already booked it. And she goes, alright, well

Katie:

Yeah, we'll talk about that offline. No, I'm just kidding. I'm

Henah:

Kidding. That doesn't happen.

Katie:

That actually has happened

Henah:

Before. Okay. Rarely it happened. One time that

Katie:

Is actually a frequent Henah is a, Hey, I booked this trip. Is it cool if I take PTO?

Henah:

That is go, well, that is not true. You've already booked one time,

Katie:

Booked it. So I guess the answer is yes.

Henah:

The only time I ever did that was to Bora Bora. Every other time I've been like, Katie please, may I please go. I'm thinking

Katie:

We're going to do a Henah roast at the end of the year where we just air out her PTO schedule all of her time.

Henah:

Hey, I'm happy to defend it. Okay. You've literally talked and told people she takes her PTO. She uses it, but she also plans in advance.

Katie:

It's true. You're a good PTO user. Thank you. You use a lot of it, but you are very good about not leaving people in a lurch when you leave. So it's cool. But I guess that's a good endorsement of he's tips because she'd be traveling, Henah be traveling.

Henah:

She be traveling. But also you make it sound like I'm gone for 12 weeks of the year, which girl I wish. But

Katie:

I'd say closer to eight or 10,

Henah:

Not 10, maybe eight in total with

Katie:

We'll check the backend and report

Henah:

With company holidays.

Katie:

Like two and a half months a year. She's got a good thing going here. No one feel too bad for Henah.

Henah:

Who’s feeling bad for me? I'm thriving.

Katie:

Oh man. All right. I'm just kidding. Okay. Well, the good thing I think about, even though planning a lot in advance can feel maybe, I always feel a little bit like, oh my gosh, it's just another thing that I have to do. But I think there is good research that backs up the fact that the anticipation of a trip is oftentimes the best part, and it is really fun to feel a lot of anticipation leading up to something. So if you are planning really far in advance, you get to benefit from that awesome feeling of anticipation for even longer. That is all for this week's Rich Girl Roundup, and we will see you on Wednesday to talk about redefining what is enough.