Hotel Room Upgrade Success Stories: 4 Video Walkthroughs

In a previous post, we learned how to email hotel managers for free hotel room upgrades. Here, I’ll share some success stories. The point? I want to inspire you to do the same. Then you’ll have success stories of your own to share: with friends, family, colleagues, and, if you’ll have us, My Points Blog. Do so in the comments section below or reach out to us via the Contact page. No textual Deep Dives here–just plenty of eye candy sorted by year. Enjoy. Or try to. Please excuse the poor videography in advance.

Wyndham Koloa Landing, Kauai, Hawaii (Anniversary Celebration, Sept 2016)

Took the in-laws along on this one as we had two master suites. While the location in a prime building and floor was the result of a well crafted room request email, we paid around $30/nt extra to unlock the second master suite bedroom for my in-laws. A lot cheaper in points than booking two separate rooms.


InterContinental De La Ville Roma, Rome, Italy (Birthday Celebration, May 2015)

Prelude to a 7 night Western Mediterranean cruise. With a balcony above the Spanish Steps, looking out to the dome of St Peter’s Basilica in Vatican City and Rome itself, this was well worth the effort. In this case, I paid around 30 euro a night extra for this particular view (around $30 dollars per night).


Hilton Waikoloa Village, The Big Island, Hawaii (Birthday Celebration, May 2014)

This shows the Power of Wow. A 1500 square foot suite, with 5 lanais, on a free stay? Mind blowing.


Hilton Molino Stucky, Venice, Italy (Birthday Celebration, 2013)

I was politely impatient as we waited to check-in. Room not ready yet. Waited more. Checked again. Not ready. Squirmed more. Checked again. “Sir, please don’t worry; you are being super-upgraded.” Super-upgraded? OK. This signore wasn’t joking. See for yourself! This was a watershed moment. From here onward, I vowed to email hotel room special requests to all managers at every notable property each and every time.


This has been a selection of only 4 of the most impressive upgrades my wife and I have received. There are more walkthroughs on the My Points Blog YouTube channel. We’re looking forward to seeing what emails to hotel managers in Japan and Maui bring us for another Anniversary trip in late Sept of 2017.

So, the upshot: you can do this! Get jazzed. Read the post showing how to craft such emails and best of luck. But in this case, you’re making your own luck. Don’t wait until check-in to see if the Front Desk staff can accommodate a special room request. Send a detailed room request well in advance of arrival for potentially stunning results.

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