Cool thread. I'm a Wifi nut myself. Apart from my laptop, one of the features that drove me to get my current phone (Nokie N80) was the built-in WiFi in addition to 3G.
That said there the type of hotspot that would be cool and useful depends on the gadget you're using, whether it's a laptop or a WiFi enabled phone/PDA.
For laptops, I need a hotspot that has access to tables to work on, and plenty of AC outlets (laptops on battery power operate at a diminished capacity - dimmer screens, etc). This invariably means the cafes/coffee shops like Seattle's Best or Coffee Tea and Bean Leaf - good facilities, terrible refreshments! Amenities like food are almost secondary but I'm tired of coffee and pastries. If you can give me Coke light that will suit me fine.
Wi-Fi in these places is not free, but I have an Airborne Access account anyway, so its just a matter of logging in. Most public hotspots I see are powered through Airborne Access anyway, more so than Globe Wiz.
Free Wi-Fi is not as common - some malls have this though, such as Robinson's Galleria and the Robinson's mall at Cybergate (Pioneer ---near the Globe Telecoms Plaza and right beside the Cybergate buuilding that houses BPO companies like Accenture).
If you can find a spot with tables and an outlet, then you're good to go with a laptop. But for malls, this is when I prefer using a handheld WiFi device. Applications in my case would then be checking my e-mail, instant messaging, surfing the news --- or checking the threads at Talk.PhilMusic.com
If I had a Windows Mobile device I would probably be using Skype on it as well.