Once upon a time, I judged almost every travel decision by one thing: the price.
Traveling with four or five kids will teach you to count every penny pretty quickly. A hotel room wasn’t somewhere we were going to lounge around all day. It was somewhere everybody could sleep, shower, and pile their stuff before we headed back out again.
If one hotel was $30 cheaper than another one, there had better be a very good reason I wasn’t choosing the cheaper one.
These days, things are different.
Most of the time, it’s just my husband and me traveling. We have a little more room in the travel budget, and after years of trips, I’ve also figured out which things are actually worth paying extra for.
That doesn’t mean I suddenly enjoy wasting money.
I still want the best value I can get. I still compare prices. I still use points, military discounts, annual-pass discounts, rewards programs, and whatever other legitimate deal I can find.
But I’ve stopped assuming cheapest automatically means best value.
There are a few things I will happily pay a little more for now because they make the entire trip better.
1. A Better Hotel Location
This may be the biggest one.
Years ago, I would absolutely drive another 20 or 30 minutes if it meant saving money on the hotel.
Now?
It depends.
If spending a little more puts me close to what we actually came to do, I’m probably paying it.
That might mean staying closer to the theme parks, choosing a hotel where restaurants are within walking distance, or staying right in the area we want to explore instead of saving $25 a night somewhere off the beaten path.
Because the cheaper hotel isn’t always cheaper once you add extra driving, parking, gas, rideshares, and — something I value a lot more now — my time.
A good example is why we LOVE the Yacht Club and Beach Club. Not only are they nice resorts, but I can walk right into Epcot. Or, if I’m feeling energetic, I can walk the mile to Hollywood Studios. I’m not spending a lot of time waiting on transportation. There are also boats, buses, and the Skyliner nearby if I need them.
We may spend more money on these resorts, but what we save in time and convenience is something I’m absolutely willing to pay for.
At this stage of my life, convenience has value.
2. The Room Location I Actually Want
I used to think paying extra for a preferred room was ridiculous.
The room has a bed. That room over there has a bed. Why am I giving you more money?
And sometimes I still feel that way.
But at a big resort — especially someplace like Walt Disney World — room location can make a noticeable difference.
After spending all day walking around a theme park, I don’t necessarily want another hike across the resort just to get back to my room.
If a preferred room puts me closer to transportation, the lobby, restaurants, or the places we’re going to use every day, I’ll at least consider it.
I won’t automatically pay for the most expensive room category. The upgrade has to solve an actual problem.
That’s really my rule for most of these:
I’ll pay more for convenience. I won’t pay more just because something has the word “premium” attached to it.
For some resorts at WDW, like Port Orleans Riverside, preferred rooms make sense. The resort is HUGE! They will tell you at the desk when you check in it can take 15 to 20 minutes to get to the shop and restaurants from some regular rooms. Preferred rooms are next to the bridges, or better yet, right near the main building. So worth it!
Now Port Orleans French Quarter? It is the smallest Disney Moderate resort. Preferred rooms do put you near the main building, but there are only seven guest-room buildings in all. It doesn’t take long to walk from any of them to the main building or the pool. So there, I would save my money.
3. A Hotel That Makes the Stay Part of the Trip
There is a difference between needing somewhere to sleep and choosing a hotel because I actually want to stay there.
On a road trip where we’re pulling in at 9 p.m. and leaving at 7 a.m.? Give me clean, comfortable, safe, and reasonably priced.
I don’t need a resort.
But if we’re spending several days somewhere, using the pool, having breakfast or drinks at the hotel, sitting on the balcony, or taking an afternoon break?
I’ll spend more for a hotel I actually enjoy.
That’s especially true on trips where the hotel itself is part of the experience.
Sometimes the best value isn’t the lowest nightly rate. It’s getting more enjoyment out of the hours I’m already paying to be on vacation.
One of my favorite examples is when I asked one more question while pricing our Universal Orlando stay and found out Club Level at Hard Rock was only $16 more for our entire stay. That was exactly the kind of upgrade I was willing to grab because the extra value was obvious.
4. Comfort on a Long Travel Day
My tolerance for making myself miserable just to save a few dollars has gone way down.
I don’t need luxury everything.
But if I know we’re going to be in the truck for hours, walking for miles, or otherwise having a very long day, I’ll pay for the things that make that day easier.
That could mean better shoes, a more comfortable hotel at the end of the drive, reserved parking, a seat upgrade, or something as simple as buying the road-trip item that prevents us from having to deal with an avoidable headache later.
Twenty-five-year-old me might have looked at some of those things and thought, We don’t need that.
Almost-60-year-old me sometimes says, Nope. We’re buying the comfortable option.
And I’m perfectly fine with that.
Do we like staying at Embassy Suites because we know they have nice, big rooms? Yes. Will I choose Hilton Garden Inn because the lobbies give us enough space to meet family and have dinner without feeling crowded? Also yes.
Comfort matters, and I will pay a bit more for it.
5. Experiences I Know I’ll Remember
This is probably the biggest change in the way I think about travel money.
I don’t automatically ask, “What’s the cheapest way to do this?”
Sometimes I ask, “Will I be glad I did this?”
That doesn’t mean every dessert party, room upgrade, tour, special ticket, or VIP experience gets an automatic yes.
Far from it.
Some things aren’t remotely worth the price to me.
But if there’s something special that fits the trip, fits our budget, and I know we’re likely to remember it years from now, I’m much more willing to spend the money than I used to be.
I spent a lot of years planning trips around what worked financially for a big family.
I’m grateful we took those trips.
But this season of travel is different.
Now I get to occasionally choose the balcony.
Or the room that’s closer.
Or the experience I’ve always wanted to try.
And that’s pretty nice.
I Still Want a Deal
None of this means I’ve turned into a luxury traveler.
I haven’t.
You’ll still catch me comparing hotel rates, watching my Hilton points, checking military discounts, hunting for ticket deals, and asking whether an upgrade is actually worth the money.
That’s part of the fun for me.
The difference is that now I’m looking for value, not simply the lowest number on the screen.
If the cheaper option gives me everything I need, I’ll take it every time.
But when spending a little more gives us a noticeably better trip?
These days, I’m willing to do that too.
Because after years of traveling, I’ve learned something:
Saving money is great. Spending it on the right things is pretty great too.