I'm not sure I quite understand your question. How would signing up to Skype or 'The Cloud' give you WiFi access wherever you go? You can only gain access to WiFi when you're in range of a WiFi basestation. If you need more continuous coverage, then 3G is the way forward because, generally speaking, cellular coverage is better than WiFi coverage.
Find a Starbucks or a Panara And thy usually have free WiFi. I'm sure there are lots of other places that have free Wifi....I've found several. Maybe purchase/download a WiFi detector software and that will help you discover WiFi networks.