Over the weekend, I was looking for some Manhattan accommodation between 8th and 13th December this year, for a vacation that a friend and I are taking. Not a city that’s known for value hotels, I started with the obvious websites, and moved on to the ‘riskier’ ones:

Graph showing increasing risk with increasing reward, with points A to E going up the scale

  • A: The usual suspects. Expedia, Travelocity, Opodo, Orbitz. Standard hotel booking agents, offering standard-ish prices, but you know what you’re getting.
  • B: Hotwire. Choose a location and a hotel rating, and you’re given prices but without the hotel name. A bit riskier, but can be better value.
  • C: Priceline. Choose a location, a hotel rating and a price, and it automatically books anything that matches. Pretty risky, but the rewards (lower price) can be significant. I book most of my hotels through priceline, but this time it failed me, so I moved on to:
  • D: Craigslist

    • . I think this is the way I’m going to go. Plenty of vacation apartments to rent, at reasonable prices. Of course, you don’t exactly know how much the vendor is/isn’t telling you, but for the money saved, it’s worth the risk.

  • E: Couch Surfing. A great site, and would have been my option of choice, had more Manhattanites signed up for it. Find a couch (usually free!) anywhere in the world, and meet new people while you’re at it. There are elements that reduce the risk (e.g. an ebay-like feedback system), so it’s not as dodgy as it sounds.

What else could be offered using this high-risk/high-reward model? Because sex sells on the web, an obvious choice would be a ‘blind date’ service (this might already exist?). Put in some basic details, and following a similar format to priceline, if anything matches, it’ll arrange a place and a time to meet. If you’re lucky, you’ll end up with Scarlett Johanson. If not, you’ll end up sitting next to a nutter like Ann Coulter (or for British readers, the very unlucky would get Linda Barker).

Maybe a map/directions service could also use something like this. “I’d like to go for a drive, for about an hour, starting at this point”. It’ll then give you directions to a random place within your specified limits. Not sure if this is useful, but could be interesting for a boring Saturday afternoon.

I also thought about online grocery shopping. It would be great if a random selection of international vegetables and breads landed on your door-step, but you’re just as likely to get four cases of dog food and some icing sugar.

Anyone have any other ideas for a high-risk/high-reward web site?