We did this morning. She looked at our booking, said 'Oh yeah, 5C. Maybe we didn't have a better room available.' They don't care here. Typical Caribbean in fact. The GM here, Will Oakley, is the invisible man.

High-end properties have kept files about their HVC's for generations. Used to be paper folders, now it's a simple database. Likes & dislikes. Things the guest really appreciated or did not want.

That is why they remember that you ordered sparkling water the last three times and there are bottles of that brand in your room, a specific bottle of wine and so on. I have been assigned to the same room multiple times simply because, at checkout, I commented that I really liked it.

The flip side is that some properties consider it crass to ask. They do things large and small and consider them nice touches. Ask for it and you can expect to pay.

At the mid-level, by all means ask at check-in. Be direct. It is a business transaction. If the FD tells you that it has a 2-BR suite for $10K, just say no thanks. If you are offered an upgrade, make sure to ask if there is a charge.

If this is a leisure trip, use a TA which specializes in the destination. Forget about program agents and stick to people who focus on the area. If there are 10 luxury properties, one is better than the other, all depending on your preferences and it is the little things that matter. The TA's who handle that business will also make a call (note a call, not an email) for you and see what they can get done. It also helps to have a TA who deals with the property a lot. You may not be particularly special, but the TA sends a lot of business and if something goes wrong, making you happy becomes important.

If this is business, most corporate TA's have a few tricks up their sleeve. They may save those for the C-levels, but if you treat them well, they may treat you well.

The best advice is to be honest with yourself and book the minimum room category that you will be happy with during your stay. That way if an upgrade is not possible, it will not sour your trip.

I agree that awareness of occupancy levels will go a long way. If there is a wedding on property, or if there is some huge event in town, or if it is a school holiday then chances of an upgrade will be significantly less.

Keep in mind that some hotels have such huge differences between room categories that they may assume you would like to keep the room that you booked, unless they are made aware otherwise.

Some destinations or hotel types play by different upgrade rules - for example Las Vegas.

You can find all of my upgrade tips here.

This is important. If you convey a specific requirement (e.g. adjoining/connecting rooms) they will often assign you a room in the category paid for and not upgrade. If you'd prefer an upgrade have them note that. Works for me.

Same with king vs 2 queen/double beds. Usually when I ask for an upgrade when I reserved a room with two beds, they'll happily do it, but just tell me that the next category up either is only a king or a king and a pull out sofa.

We went to Indonesia in May 2009--very low season there. Amanusa gave us free day room in transit due to low occupancy. Amankila upgraded us from pool suite to Indrakila suite due to low occupancy (and my request in advance). Amanjiwo gave us free use of Amanjiwo suite for one full day due to no occupancy. Amanwana let us leave early due to poor diving conditions and air con issues at no extra charge and then upgraded us to the Amanusa suite at Amanusa for the remaining nights, all possible due to low occupancy.

We went to Azura Benguerra in May 2010 for part of our honeymoon. I negotiated in advance to get their Presidential Villa at substantial discount (about 60% off) since it was low season and that villa was unlikely to be booked. We paid only about 20% more than a regular villa would have cost.

We went to the Halekulani in September 2008 and booked Diamondhead Room but made sure to advise we needed good air con reaching 68 F or lower. Air con didn't work well...so they upgraded us to th Diamondhead Suite at no extra charge for failing to deliver on promise. Wouldn't have been possible except it was low occupancy.

We went to Vatulele Island in May 2005. We stayed 10 nights and got a "book 4 get 5th night free" deal on their two top accommodations at the time: the Pink House and the Point. I negotiated a further 25% off those rates since we were staying so long and since they had such low occupancy expected at that time. (They were only 1/2 to 2/3 full, including some of the owner's relatives, during our stay!)

We went to the FS Mandele Bay in September late 2000s, I'm not sure the exact year. They mis-advertised the diving schedule, which was the reason for our trip. They handled it very poorly. In the end, to make it up to us, I told them to give us private diving at their expense. They instead offered a shore excursion for the bad day in question...and upgraded us to the 3rd biggest suite. That was available only because of low occupancy.

We went to Amangani in May 2012 with our mothers...and we got upgraded into their Amangani Suite due to lower occupancy and because I asked. Having paid for 2 rooms and having a friendly Aman GM email the Amangani GM on our behalf also was a big help.

We went to the Park Hyatt Istanbul on a points reservation for a suite in October 2013--and I had no status at that time. The hotel apparently had no true suites available for that category booked (they said they only had 5) and tried to put us into a "spa suite" which really was just a junior suite. I insisted that we booked a proper 1 bedroom suite and that's what we were due. They balked but I persisted--because we like proper suites so I can make the bedroom cold for me, and the living room warmer for my husband. They ultimately agreed the error was theirs and gave us the Terrace Suite, a massive 1 bedroom specialty suite with incredible views from its huge terrace overlooking the Bosphorus.

We went to the Strand in Rangon, Myanmar, 2-3 years ago in Jan. I negotiated the Strand Suite for 20% less than was advertised by agreeing to stay 3 nights instead of 2 by comparing the offering to the almost sold out Governor's Residence junior suite rate. I took advantage of the changing management from GHM at the time.

You can negotiate and you can press. Most people don't want to do that. I do...and I often get more because of it. I don't always get more...but I always ask or try.

low value upgrade, breakfast, 100 credit are not valuable on expensive stay
"programs" seem to be limiting 'contracted/published' upgrades more now

upgrades at FS seem to be more about whether one is regular at FS hotels

anyone can negotiate with management, especially when it is low occupancy
Trogger, people who negotiate for a living can be very successful with hotels
many here negotiate successfully at hotels, most of them do not post about it

We booked the 4S in Amman using FHR. When we got there, no upgrade for us. As it turned out the hotel was packed due to a wedding. I'm sure they took up all the good rooms and there was legitimately no place for them to upgrade us.

Traveling in a less busy time would have given us a much better chance. Sadly, we only have ability to travel during summer or school holidays and never get to a place that isn't on the more crowded side.

My inlaws went to Central Europe and booked with a TA that is FSPP and all that jazz. When they checked in to the hotel (Gresham Palace), the GM or sales manager came running out to meet them. He personally knows the TA from when he was in California.

But, as the bible says..."ask and ye shall receive" or something like that. If you don't ask in some fashion, I think the likelihood is much lower.