Just during Covid...but we did get some AWESOME upgrades during that time.
Yes in I think 1999 or maybe before, it was definitely pre-Internet/email so maybe 1994? It was one of our big anniversaries. We were staying at the Boardwalk, we faxed and asked very very nicely Since it was a special trip. When we got there they had put us in one of those garden bungalows with the white picket fence, and it was wonderful. when we walked to the unit there were bunnies eating in the little garden, I mean it was like right out of a Disney movie (cue Snow). Seems like the Boardwalk was somewhat new then, sorry my memory! I’d have to go back and look at a real photo album to figure out the exact year. It was around this time we started going twice per year. But again this was years ago and it sounds like things are really different now. We go next month and won’t ask, we’re basically paying for our upgrade this time since we haven’t been in 13 years. I would add that in all the times we went every year this was the only time we ever asked for an upgrade.
Funny you should post this. Back about 20 odd years ago, before true social media when there were only message boards like the DIS, passporter, rita aero's sites, intercot, etc., i wrote an essay entitled 'how to schmooze an upgrade at disney hotels'. Many people used my points successfully at wdw and at hotels all over the world in fact, or so they told me. For me, throughout the years, we have been upgraded a bunch of times. The best was a few years back being upgraded to the Steeplechase Suite at the BWI from a deluxe CL room right after it was upgraded to Bob Igers liking since it was his favorite resort. In these later years, we usually book the deluxe cl rooms so there really isn't a room to upgrade to but for the 2 bedroom suites and since we are usually just 2, it would make no sense(our daughter was with us for the Steeplechase upgrade).
Those tree houses rocked! We did a triple split stay one year and our first part was there, really fun
On our last trip we were upgraded at Boardwalk Inn. It was a trip to celebrate our 35th anniversary and my husband's birthday. We had booked a standard view (or maybe garden view) room and requested a high floor. We didn't get to the resort until around 10;30pm. When we checked in the cast member told us she was sorry, but they didn't have any rooms on a high floor left, but she put us in a room with nice courtyard view. That was perfectly fine with us. She told us she was going to watch and see if a room like we had requested would open up in the morning, and she would call and let us know. A short while after we got to the room she called us and said the would like to offer us one of the Garden Cottages in the morning, if we would like to stay there
We didn't really know anything about the room, but were happy to try it. Turns out it was a giant upgrade, including being a club level accommodations! It was really nice, and such a big, unexpected treat. When we would see the cast member during the week she was always checking up on us and asking us if we were enjoying our stay. She was just the sweetest. It was a special stay that we will never forget!
We were upgraded to one of the cottages as well.On our last trip we were upgraded at Boardwalk Inn. It was a trip to celebrate our 35th anniversary and my husband's birthday. We had booked a standard view (or maybe garden view) room and requested a high floor. We didn't get to the resort until around 10;30pm. When we checked in the cast member told us she was sorry, but they didn't have any rooms on a high floor left, but she put us in a room with nice courtyard view. That was perfectly fine with us. She told us she was going to watch and see if a room like we had requested would open up in the morning, and she would call and let us know. A short while after we got to the room she called us and said the would like to offer us one of the Garden Cottages in the morning, if we would like to stay there
