The site http://www.hotelwifitest.com/ aims to do this sort of thing; I don’t know how good it is.
The biggest problem with hotel wi-fi (and conference centre wi-fi) is us. Travelling nerds who need 2 or 3 IP addresses each (and try to do their work each evening while regular people are watching TV) typically bring these systems to their knees. I’ve had so many hotel people tell me they never get complaints like these the rest of the year, and I actually believe them. Therefore, the system would probably report the wifi was fine most of the time. But when you need to download that video while uploading the new giant PowerPoint, all while your email comes in and you sync with source control, you would declare it horrible. And it’s worse when 75% of the rooms in the hotel contain people who are doing the very same thing, but the system is sized for 10% of the people checking email and looking at pictures of their grandchildren.
I think your best bet is a plan B. Those USB-stick thingies are going to be mine. I have also left the hotel and gone to Starbucks. Sometimes when the conference centre sucked I went back to the hotel, and once when the hotel sucked I went back to the conference centre. On that occasion the hotel wifi just plain sucked – I couldn’t even read email or load web pages. But perhaps it would have been ok during a less nerdy week.
Are you only talking about hotels in your own country, or do you also visit other countries frequently on your trip?
In New Zealand the WiFi/Broadband connections in hotels are either non-existent, not included (some charge you an extra $25/day for wifi!) or terrible slow; that’s why i carry my own 3G modem stick whenever i leave my house. Faster and cheaper in most cases, plus i wont have to fiddle with my computers network settings each time i set up camp somewhere.
You might be able to try asking questions each time here with a shortlist of the places you have in mind.
I assume you are already reading the reviews on HostelWorld, HostelBookers, and TripAdvisor? They won’t necessarily cover the net connections in the places but they might.
One trick is to look up the place on Foursquare – if people have checked in on wifi, it’s a sign there’s likely free internet, and often if the connection is poor, people comment on that on foursquare as well.
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