The Mystery Behind Free Room Upgrades

If you’ve even skimmed through TripAdvisor or Facebook travel forums you’ll see messages from people wondering about the mystery behind free room upgrades.

I would say it’s one of the most frequently talked about subjects.

And I would say it’s a question that has no real answer.

I’ve been given a few free room upgrades over the years, and every scenario was different. Let me detail a few different scenarios.

My Free Room Upgrades

Scenario 1

On our first trip, we booked the lowest-level room category that didn’t include a patio or balcony, faced a garden, and featured the lovely sounds of highway traffic. But when we got to the resort, we were escorted to a room that couldn’t have gotten any closer to the beach. We had our own set of stairs that led to our private balcony. My first morning I woke up to the sounds of waves crashing against the shore. I thought I was dreaming. Seriously.

The scenario in this case: we were there to get married.

Scenario 2

On another trip, we were handed an index card at check-in that told us the name of the room we were booked in and the name of the room we were upgraded to. Again, we had booked the lowest-level room category that had no balcony or patio and was located on the 2nd floor of the main lobby. Instead,  We were escorted to a villa that came equipped with a private walk-out patio area and a beautiful oversized room with a corner Jacuzzi tub, and we had a shared private pool. Friends who accompanied us on the trip were given an even nicer complimentary upgrade – theirs included a beautiful ocean view.

The formula? We were return guests to the same chain, Sandals, but that doesn’t totally explain it. Our friends were not, and they were given an even nicer upgrade. So was the resort trying to lure the newcomers in by offering them a nicer room upgrade than what they offered the returning guests? One can only wonder.

Scenario 3

A few years ago we returned to the resort where we were given my first upgrade, and I was surprised that despite being a slower time of year (mid-December), we were not given a free upgrade. I’ll admit that I was disappointed, so I asked if there was a chance I could be upgraded. They informed me that they would do their best to accommodate my request. Two to three days later, we were in a beautiful room steps away from the beach, in the same category upgrade as our first visit.

The formula? Returning guest, I asked for it.

Scenario 4

I researched room locations for the resort we were going to, and, after deciding which building I was interested in, I discovered that the room categories in that building would require an upgrade (again, I booked the lowest room category), but I put in the request anyway. When we arrived to the resort, they escorted me to the exact building I requested, with a room upgrade three levels above what we paid for.

The formula? Returning guest, I asked for it.

The Speculation

So while it’s easy to guess that my luck has been a result of being a loyal and return guest in a few of these scenarios, there have been many trips where being a return guest definitely did not get me an upgrade.

So what about new guests? I’ve been upgraded on my first visit to some resorts but not to others.

What about special occasions? I was upgraded on my destination wedding trip and so were other fellow-destination couples that I know, and at various resorts/chains. But I have friends who married on the same resort as me who didn’t get a room upgrade. As for wedding anniversaries, I have been upgraded at some but not at others.

The Key to Getting Free Room Upgrades?

Considering all of this, I can’t seem to figure out a formula that gets you a free upgrade every time. It just doesn’t seem to exist.

I would say the majority of times it’s simply based on availability and luck of the draw and not on who you are or what your circumstances are, although I’m sure there are times those things come into play. I think they go through their list of check-ins one by one and look at what rooms could be assigned to that person. That may result in an upgrade or it may not. There doesn’t seem to be any magic formula.

And when these upgrades do happen, they’re usually not substantial upgrades. For instance, if you’ve booked the lowest-level room, it’s doubtful (maybe not impossible) that you’ll be upgraded to the top-tier suite with butler service and all the amenities you could ever ask for. My upgrades were always to a room about $500/week more expensive than what I was booked in. That’s huge, I know, but I wasn’t being bumped up to a penthouse suite by any means. Those are reserved for either the people who booked them or the people who booked a grade or two below that level and are lucky enough to receive the upgrade.

My advice is this: you should always book the room category you’ll be happy with and never go there expecting a free upgrade, because if you don’t get it, you’ll be stuck in a room that makes you miserable. Book the category you know you’ll be happy with and if you get a free upgrade, see it as a bonus!

By all means, if you really want a complimentary upgrade, put in a special request to the hotel upon booking or a few days before you arrive. You never know.


If you have figured out a method of securing a free room upgrade, by all means, let me know in the comments below! It’s a mystery we’d all love to solve :)

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One Love.
Jody, The Tropical Tourist


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