There is lots of software available to help you do this. Following other peoples blogs is one way to learn about this. These blogs vary. I think the one I enjoyed the most is at Andy Ganner's blog. This is a sort of comic novel about a group that traveled by bike across Russian in 2001. There are probably many more. (Another one I found funny was this one by Edward Genochio).
In any case, the first thing you will want to be able to do is to show people where you are. The way you do this is to use Google maps. They provide an API that will allow you to draw one of their maps on your webpage with a little flag that will illustrate where you are. I won't try to explain how to use it. You need to ask for a key from Google for each web domain in which you want to display maps. The best way to learn what to do is to look at their instructions. This is the method that was used to shows the maps on the Russia Crossing page on this website. This isn't much help when all you want to say is that you just arrived in Calgary. However, if you are riding through Carnduff Saskatchewan, or Syropyatskoy Russia, it really clarifies things.
Once you set this up, the problem you will discover is that the map api requires that you provide pretty accurate longitude and latitude numbers for your location. I suppose that gps devices are pretty common now. If you have a gps device, then you could enter your gps location every night when you visit the internet cafe.
I always thought this was a little creepy. If you set up your web blog with a google map, then record your location every night, you are advertizing to the world that you are in a remote place with nothing but a bicycle. Yet you are rich enough to afford a gps device. This doesn't seem wise. Of course, your blog isn't really public - only your close friends and family are actually looking. This always reminds me of my cat. When he wants to hide, he sticks his head under a cover, then figures no one can see him because he can't see anyone.
In any case, another way to figure these latitude an longitude things is to use the following excellent website. I am not sure exactly who to attribute this excellent website to. It provides a google map. You click on the map, it gives you the latitude and longitude, which you can then put on your own map. Of course, to use it, you need to know the name of some exotic location. This isn't really a problem in Carnduff. It can be in remote parts of Russia.
The idea is that where every you happen to be, you can display the time there, and what the weather is like. These are very straightforward. If you aren't familiar with them, the time and date website will not only give you instructions, but actually give you the html code to put on your webpage. Exactly the same thing applies at the weather website. The only complication with using these two things, is that you have to alter the locations manually by looking up the appropriate codes for your location, in order for them to give the right times and forecasts.
Finally, for shorter tours, there is a really useful website at mapmyride.com. This is based on google maps. There are gazillions of rides marked out on this website and you can make up your own rides and contribute them. Here is a ride around Vancouver:
This is pretty neat. If there is a downside to this website, it is that it can be very slow. You might already have noticed that putting a map on your webpage makes your webpage just as slow.