Naming is Hard

At the moment, I’m trying to plan a multi-city break to Toronto and New York with my girlfriend. The flights to and from Toronto are already booked, but I need to sort out a hotel in Toronto, flights to and from New York and a hotel in New York. No big deal, right. Fair enough, but this is complicated by the fact my girlfriend is already in Canada and even Skype isn’t making discussing these things easy.

When I started planning this trip a few days ago, my first thought was that I needed a way to store all the various configurations online so that my girlfriend and I could work out what was best. Assembling the options online would mean we both had them at hand and would help to reduce confusion. Anyway, I set out with the thought that surely trip planning’s quite common in this day and age and there must be a decent Web 2.0 app to help me out. First of all, I tried Yahoo! Trip Planner. Unfortunately, my patience waned after only a few minutes. Trip Planner isn’t a particularly accurate name, since it doesn’t deal with how to get “there”, only where to stay and what to do once you are “there”:

Even though it wouldn’t help me with the flights from Toronto to New York, I gave Trip Planner the benefit of the doubt and tried to compare New York hotels. This was futile as Trip Planner presented me with a list of hotels which I could sort by popularity or name. WTF?! Isn’t Yahoo a search company? I wanted to find hotels which could accommodate my girlfriend and I on specific dates and order them by price and location.

(Btw, I like the look of the price at the four-and-a-half star Plaza)

At this point, I pretty much gave up with Trip Planner. As much as I Googled, however, I could not find the app I was so sure would have existed. (If you’re thinking of building a Web 2.0 app, there’s an opportunity here!) I asked Jane and she couldn’t do any better either.

Enter Backpack

Having tried the domain-specific solution, I re-considered my problem. Although what I was trying to do—plan a multi-city trip—was quite specifc, it was simply an organisation and collaboration problem. There were loads of tools built for collaboration—why not use one? I chose Backpack because it’s a tool I’m familiar with and also because my girlfriend has a Backpack account as well and Backpack allows you to share pages. Looking back now, it’s the obvious solution—just look at the name.

Anyway, I set up a page for my trip and starting adding notes. What I hadn’t realised is that since I last used Backpack (a few months ago), 37signals have beefed up the page components. My planning fell into natural sections: flight to Toronto, hotel in Toronto, flight to New York, hotel in New York, flight from New York, and flight from Toronto. I wanted to keep these distinct but also on the same page. To do this, I used a new Backpack feature: dividers.

Dividers are a great way to organise a page into sections. Each divider can have a title, or you can have a simple line if you’d prefer. I created a divider for each section.

Next I added notes for each small nugget of information (e.g. Air Canada flights on Monday or details of a hotel) and dragged it into the right section. I chose notes so that I could build up the information progressively and re-order items based on how good I felt they were.

Finding Hotels.com

After a while of lurching about on the ‘net looking for New York hotels, I stumbled upon Hotels.com, which is a Hotel search engine with lots of search options and great features. I put in my options and went through the list of hotels, creating a note for each one that was promising. For each hotel, I linked the note to the Hotels.com overview page which gives you the address, a summary, user reviews and price information. It also gives you a total estimated price in GBP which is very handy since New York accommodation taxes are too complex for my tiny brain and dollar prices don’t mean anything to me. The mapping feature gives you an at-a-glance idea of where the hotel is in relation to the sights. All in all, I’d recommend Hotels.com highly for hotel comparisons.

Mapping hotels

While it was good to know where each hotel was individually, this didn’t help when looking at the whole list and trying to trade-off price and location. I wanted to be able to see all the hotels on one map to compare where they were. For this, I turned to Google’s recently released My Maps feature which gives you Google Earth style map annotation right within the browser. I created a map for the New York hotels and a map for the Toronto hotels. Each hotel has a blue pinprick and is labelled with its name.

Best-of-breed versus All-in-one

What this exercise illustrates to me is the trade off of using several best-in-breed applications (Backpack + Hotels.com + Google My Maps) versus one all-in-one monolith (Yahoo! Trip Planner). In this case, the best-of-breed approach worked best for me. For the average consumer, it might be too much to ask to tie in several different information sources manually but for me it worked well. In this case, the all-in-one solution did not offer enough flexibility or functionality to help out, but there are obviously situations where the connectedness of the solution would offer great advantages. To me, there is a third way: tieing best-of-breed applications together using APIs and this is a key feature of Web 2.0. Unfortunately (or fortunately if you’re looking for opportunities), there doesn’t seem to be a good product in the trip planning space yet to compare.