Several months ago I began checking in to places on Gowalla.

What first turned me on to Gowalla was its design. The website and mobile apps are beautiful, and Gowalla’s use of cute icons and graphics throughout makes for a great experience.

But it’s not just the design that I like about Gowalla. It’s fun, and it’s meant for people who like to get out, whatever the reason. Errands, dates, local events, road trips, and the like — if you like to get out you might like to Gowalla.

And this focus on travelers (adventurers?) is what makes Gowalla so interesting and fun for me. I don’t have to have a metric ton of “friends” on to make it worth using. And though I suppose it would be more fun to use if more of my friends Gowallad, chances are good that even the 30 friends I do have aren’t paying much attention to where I check in. And that’s okay. Because what is most enjoyable about Gowalla is the cataloging of your own journey.

I just returned from a two-week vacation in Colorado. On the first day of our trip I put the Gowalla iPhone app right on my home screen and decided that while I was traveling around the Colorado Front Range and the Rocky Mountains I would check in at every spot I could.1

Also, in preparation for my Colorado vacation I created a Gowalla trip called “Classic Castle Rock“, which features some of the premier spots around my home town. I built most of the trip on the Gowalla website before I even left Kansas City. There were a couple spots I wanted to be a part of the trip that weren’t created already, so once I got in to town last week I spent one of my mornings driving around and creating the final few spots.

It’s unfortunate that creating new locations and checking in at spots is limited by my connection to the internet. If I’m not connected I can’t check in. And this is particularly unfortunate because some of the most fabulous, visit-worthy locations are in areas with no cell service and no wireless internet.

For instance, my family and I spent a few days in Pine Grove staying at my grandparent’s cabin. It’s an old, red cabin that sits right by Elk Creek. And a half-mile upstream is the Bucksnort Saloon, home of the Buck Burger. We also spent one morning in Bailey to have breakfast at the Cutthroat Cafe and visit Coney Island’s new location. Sadly, my AT&T-connected iPhone couldn’t get a lick of signal at any of these fabulous spots.

It just so happened that on The Big Web Show last week, Jeffery and Dan interviewed Josh Williams, the founder of Gowalla. And they discussed this very issue of mobile connectivity versus spot check-in and creation. Josh is hoping that the Gowalla team will find a way to store GPS location data on your phone even when you don’t have cellular service. Then, once you’re connected to the internet again, you could use that stored GPS location data to check in and/or create the spots you were at.

This would be a great solution considering the situation, but ultimately we just need better cellular coverage. You see, it’s one thing for me to be able to create the Bucksnort Saloon 48 hours after being there, but that won’t necessarily help someone in the area use Gowalla to find the Bucksnort when they’re out in the middle of No Network Land looking for great burger joints.

It has taken me a while to decide how I use Gowalla (though I’m still not sure exactly what that is). At first I had to check in as soon as I arrived at a spot — as if I was punching in on a time clock. If I didn’t check in right away, I wouldn’t check in at all.

Now I check in when I have a few spare minutes. But there are some people who check in to spots they don’t even walk into but that they just walk by and notice. Is that breaking the rules? What are the rules, even?

For me, I prefer to only check in at places I’ve actually walked into and spent at least a little bit of time. But even then there are times I am on the go and don’t have a few spare minutes to check in with Gowalla.

And this is perhaps the most frustrating part of using Gowalla. It usually takes at least a minute or two to fully complete the check-in process on my iPhone. And that’s assuming the spot I’m checking in to has already been created, and I have good 3G coverage. It takes an extra couple of minutes if I also need to create the spot I’m at.

I would love to see a part of Gowalla’s future solution for checking in at places where you don’t have service to also include a way to check in quickly, or even in the background. If my wife and I are out on a fancy date you bet I want to check in at J. Gilbert’s. But giving my wife the attention she deserves is significantly more important. Which is why I want Gowalla to let me check in for my hot date at the best steakhouse in town while also letting me ignore my iPhone and have a great evening out.

Coming back to my question, I don’t think there are any rules. Much of what makes Gowalla so cool is that it’s still being defined and discovered by its developers and users. Every day I seem to discover a new use for Gowalla, and as it grows the more useful and fun it will be.