Hilton HHonors - How to upgrade as a Diamond?

I am planning a trip to either Cabo or Cancun this April and trying to determine the best way to snag an upgrade. I will need 3 rooms and from past experience when i book 3 rooms none of them ever get upgraded. Im not looking for 3 upgrades but I would like to try and increase my chances of getting one of the rooms upgraded for me and my wife. So with that scenario should i book 1 room in my name and the other 2 in my kids name? or just book all 3 in my name and explain myself when i get there? The downside to booking 2 separate reservations is I will have a hassle on my hands trying to get points credit for two rooms.

Know the property you're going to stay at. When you make your reservation, in the comment box be specific about the type of upgrade you'd like. I booked two rooms in Kauai and both rooms were upgraded as I requested.

Do a search on the Cancun property. I can't remember specifically, but I believe they offer upgrades for an additional fee.

As well, always send the hotel an e-mail before you go telling them you are coming. Every resort I have been to (including the upcoming barbados hilton) every time I have sent them something they have confirmed my upgrade prior to arrival. Only in Cancun did I pay for an upgrade, and that was because I wanted a suite. In Hawaii, San Juan, and other islands I was comped at least a minor upgrade before I even landed.

Call the hotel the day ahead of time. At that point they will not what rooms they will have and you can get all your answers right then.

T&C's state that diamond VIPs are afforded only one upgrade per stay, but of course YMMV.

I've stayed at multiple different Hiltons where I've booked multiple rooms and all the rooms have been upgraded.

I suggest that you call or email ahead and ask for the upgrade. It's all about availability at the time.

FWIW, I was at the Cabo Hilton on points over New Year's 2007. Like you, I needed three rooms. I e-mailed several times and even called to make sure the rooms were contiguous. I was told it would not be a problem. When I got there, we were scattered about the property. The next day everything got fixed and they upgraded all three rooms. But I would not count on e-mail communication or even telephone communication as to room type counting for much. On the plus side, it is a hell of a property.

Know the property you're going to stay at. When you make your reservation, in the comment box be specific about the type of upgrade you'd like. I booked two rooms in Kauai and both rooms were upgraded as I requested.

What kind of updates did you ask for in Kauai? Did you request Diamond upgrade and asked for a oceanfront?
Just curious
Thanks

T&C's state that diamond VIPs are afforded only one upgrade per stay, but of course YMMV.

I've stayed at multiple different Hiltons where I've booked multiple rooms and all the rooms have been upgraded.

I suggest that you call or email ahead and ask for the upgrade. It's all about availability at the time.

Several posts about calling/emailing ahead? How many of you actually call/email ahead? Has this really altered your UG percentage?

Several posts about calling/emailing ahead? How many of you actually call/email ahead? Has this really altered your UG percentage?

I have emailed ahead at both Hilton Prague and Hilton Cavalieri and was treated very nicely and given upgrades I don't believe I would have other wise based upon other people's experience with similiar status (from reading here and tripadvisor.com)

sdcarver

I have emailed ahead at both Hilton Prague and Hilton Cavalieri and was treated very nicely and given upgrades I don't believe I would have other wise based upon other people's experience with similiar status (from reading here and tripadvisor.com)

sdcarver

Hmm, good to know. I guess I'll have to start doing this. Do you just email the manager of the hotel? Do you get the email address from the website, or from your confirmation emails?

I've found that a good old fashioned letter or card sent directly to the GM of the hotel a few weeks before arrival works wonders as well...

Hmm, good to know. I guess I'll have to start doing this. Do you just email the manager of the hotel? Do you get the email address from the website, or from your confirmation emails?

I usually don't like to bither the GM with requests for upgrades or service. I try and find out the email addresses for check In or Front Desk managers/supervisors. Kindness and flattery (as far as what you have heard about the hotel :) ) go a long way.

sdcarver

Where is the best place to find the appropriate email address. The only link I can find on the website for the DT DTD is the group/event manager.

I usually don't like to bither the GM with requests for upgrades or service. I try and find out the email addresses for check In or Front Desk managers/supervisors. Kindness and flattery (as far as what you have heard about the hotel :) ) go a long way.

sdcarver

I'll be a Diamond in a few weeks; so I'm curious as to the words you use to request an upgrade. Do you flat out state you expect an upgrade since you're a Diamond? I would assume you're more subtle about it.

I'll be a Diamond in a few weeks; so I'm curious as to the words you use to request an upgrade. Do you flat out state you expect an upgrade since you're a Diamond? I would assume you're more subtle about it.

I'm guessing it's a generic letter each FT has created from some template. To be honest, sending a letter the snail mail way is too much time/work for me for an UG. Emails might be easier.

Still waiting to hear where other FT-ers get the email addresses for the front desk managers.