Syncing iCal feeds with my iPhone: Not

Here's something I need to do, but I don't know how: sync an iCal feed with the calendar application on my iPhone, without a Mac, and without upgrading Outlook 2003 to Outlook 2007. Here's the whole story.

First, I travel. Sometimes, a lot. And I have a lot of appointment managing to do. I feel very disoriented whenever I don't have my itinerary available to me, in my pocket. I also need my schedule on my laptop, where I can see a whole month in one view. Of course, the schedule in my pocket and the schedule on my laptop need to be synchronized.

I own an iPhone. It's the first cellphone I've truly loved since the first Nokia I bought back in the 1990s. I love it. My iPhone syncs with Microsoft Outlook 2003 on my Dell laptop. I don't own Outlook 2007. I don't do email in Outlook anymore. I use Gmail, both at home and at work. And on my iPhone.

I do still use Outlook, though, for calendars and contacts. That's because I don't know a better way. I need read/write access to my calendar and contacts lists on my PC, and I certainly don't want the last copy of my calendar and contacts to be stored on a device that goes with me everywhere I go and that could easily be lost or stolen.

A better place to store calendar data is on the web. That way, I can share it with people (without other people, we wouldn't need calendars at all!), and I can access it from whatever computer happens to be available. Enter Google Calendar.

I want to love Google Calendar, but I can't. I love the idea of it, but I don't love it because I can't sync it with my iPhone. There's no direct hookup between Google Calendar and my iPhone. Yes, I know I can see my Google Calendar from my iPhone, and I remember being able to do some limited form of calendar editing from my iPhone, but that's not good enough. I need alerts when I'm not connected. I need my information stored locally within the calendar application on my iPhone.

I think the solution is supposed to be Google Calendar Sync. It syncs information from Google Calendar to Outlook 2003, where I can sync to my iPhone. But Google Calendar Sync doesn't work on my laptop. I keep getting error code 1008. I looked it up, and Google says they're working on it, but there's no relief today. Additionally, even if I could get Google Calendar Sync to work (I had it working a couple of months ago), it still doesn't do what I need it to do. That's because Google Calendar Sync syncs only my primary Google Calendar to Outlook. More on that in a minute.

Now, let me describe one of the world's very coolest web applications ever: TripIt.com. TripIt is wholly excellent. Imagine this. Book a flight at American Airlines, a hotel room at Hilton, and a rental car at Hertz. You get three confirmation email messages as a result. In the old days, you might have spent some of your time transcribing the information from those messages into Outlook or whatever. Or maybe you paid someone good money to transcribe them for you.

With TripIt, all you do is forward your three confirmation email messages to plans@tripit.com. And then all your itinerary information gets structured automatically into a complete, single itinerary that you can access on the web. You can print that itinerary on a page or two, stuff it into your briefcase, and have everything you need: flight times, rental car and hotel confirmation numbers, weather forecasts, pertinent local maps, ..., everything. 

That's not even the best part. The best part is that TripIt creates an iCal feed that Google Calendar can pick up automatically.

So let me recap. You book travel however you like. You forward the confirmation mails to plans@tripit.com. (It just occurred to me that you could even do this automatically with Gmail filters). And then Google Calendar picks up your whole itinerary automatically.

 

But for me, that's where the joy ends. Because even when Google Calendar Sync does work (remember the 1008 error causes it not to), it syncs only your primary calendar. It doesn't sync a secondary calendar obtained through an iCal feed, so it doesn't sync my TripIt calendar.

So, here's what my process looks like now:

1. Book travel.
   
2. Forward the confirmation emails to plans@tripit.com.
   
3. Print my TripIt unified itinerary for my briefcase.
   
4. Type my itinerary into Outlook (or onto my iPhone). If the travel spans more than just a couple of time zones, then I enter the itinerary at mytimetraveler.com (which does my time zone arithmetic for me), and then I download the Outlook itinerary record from the web page. Back when I could get Google Calendar Sync to work, copying my TripIt calendar records to my primary calendar was an option, but not a good one.
   
5. Sync my iPhone with my laptop.
   

Here's what I wish my process looked like:

1. Book travel.
   
2. Forward the confirmation emails to plans@tripit.com.
   
3. Print my TripIt unified itinerary for my briefcase. (Or not.)
4. Sync my iPhone with my laptop.
   

I've actually considered upgrading to Microsoft Outlook 2007, which, I understand, knows about iCal feeds. It might be able to sync my TripIt data with my iPhone. But I think the price tag is too high to pay for that one feature. And I'm not even assured that it will work. I know Microsoft has a 60-day free trial, but I'm worried that Outlook 2003 won't ever work right again if I try 2007 and don't like it.

Another option I've considered is replacing my laptop with a MacBook Pro. As tempted as I am by that idea, I'm not going to do that right now, and I'm not sure whether it would actually solve my problem anyway. Would it?

I hope there's a solution that I can implement with minimal expense, and with the hardware I own today. If there is, I sure haven't found it yet. I'd love to hear from you if you have a helpful opinion.