After perusing Costco Travel for price drops on our four upcoming Azamara cruises in 2027, he was thrilled to see that each had dropped substantially. Not a few dollars here or there, but the kind of price drops that make your eyebrows lift and your heart beat just a little faster. The same cabins. The same itineraries. The same sailings we’d already committed to, penciled into our future like promises. Only now, suddenly, there were hundreds, possibly thousands, of dollars less expensive. Please keep in mind that such price drops may only be available to US citizens.

Without hesitation, he picked up the phone and called Costco Travel.

Normally, this is where the ritual begins. You put the phone on speaker, brace yourself, and go about your day while waiting the expected 30 to 60 minutes to connect with a live human being. It’s almost a game for us at this point: How much can you get done while on hold? Laundry folded, dishes washed, emails answered, maybe even a meal cooked. The hold music becomes the soundtrack to productivity.

But this time was different.

They answered after the second ring.

We both froze, exchanging the kind of look that says, Well, that’s never happened before. Surely a fluke. A cosmic travel anomaly. Maybe someone accidentally picked up the phone too quickly. Whatever the reason, he was connected instantly, and optimism filled the room. This was going to be easy, we thought. A quick conversation, a few clicks on their end, and voilà—money saved.

Fast-forward to the present moment as I write this: he has been on the phone for over 2 hours, 34 minutes. Luckily, he’s using WiFi calling and will not be charged for the very long-distance call using T-Mobile at $.25 per minute. But even if he were paying for the call, it would still be worthwhile.

Scroll to the end of this post for the total savings.

Over two hours of polite explanations, long holds, keyboard clacking in the background, and the occasional reassuring, “I’m still here.” Over two hours of navigating the complex inner workings of cruise pricing, fare codes, guarantees, and systems that don’t always speak to one another as smoothly as one would hope. Over two hours that might sound excessive to some, but to us feels oddly familiar, part of the unglamorous side of long-term travel planning that rarely makes it into glossy brochures or Instagram reels.

Here’s the thing many people don’t realize: when you book a cruise with a lowest-price guarantee, it’s not a simple matter of pressing a button when prices drop. There is real work involved on the part of Costco or any other booking service. Each booking has to be re-priced manually. after back and forth calls with the cruise line. Each fare has to be checked against the original contract. Each change must be approved, processed, documented, and, if necessary, escalated. Multiply that by four cruises, all scheduled for 2027, and suddenly you understand why this isn’t a five-minute task.

And yet, it’s almost always worth it.

Because this is the quiet art of travel math, the behind-the-scenes effort that can mean the difference between “just making it work” and “breathing a little easier.” Saving a few hundred dollars on one cruise might cover a pre-cruise hotel or a memorable shore excursion. Saving thousands across multiple cruises can stretch a travel budget in ways that ripple outward: better flights, longer stays, more experiences, fewer compromises.

This is especially true for those of us who travel slowly and deliberately, who plan far ahead, not out of rigidity but out of intention. Booking early gives us peace of mind, but it also opens the door to these moments when patience and persistence pay off. Prices fluctuate. Markets shift. Cruise lines adjust. And when you’re paying attention…when you take the time to check, to call, to wait, you sometimes get rewarded.

Of course, there’s also a human element to all of this. On the other end of the line is someone doing their best within a system that is anything but simple. We never forget that. Gratitude goes a long way during long phone calls. So does kindness. So does remembering that this person didn’t create the complexity; they’re navigating it alongside you.

As he continues to wait, listening to waiting-time music through his hearing aids, I can’t help but smile. This is part of our lives. The research. The follow-up. The occasional frustration, balanced by those small victories that feel disproportionately satisfying. The knowledge that, even if it takes two hours or three, this effort might quietly fund another sunset, another port, another memory yet to be made.

Travel isn’t just about where you go. It’s also about how you manage the in-between moments, the spreadsheets, the phone calls, the hold music, and the patience. And sometimes, it’s about celebrating the simple fact that the same cabin, on the same ship, sailing to the same beautiful places, will now cost a little less than it did yesterday.

Here are the savings we incurred today on each of the four cruises:

1. US $3,080

2. US $1,560

3. US $1,280

4. US $  400

Total Savings: US $6,320

That, to us, feels like winning.

Be well.