Hi Aaron,
I would offer that you have a look at SailBlogs,
http://www.sailblogs.com, as one of the main sites cruisers use for keeping their on-line journals and photos. I have run the site for over two years now, and it is becoming very popular with sailors and circumnavigators.
SailBlogs can handle text, photos, video and tracking - all in a nice sailing-oriented package, and also allows you to post to the journal - both text and pics - while off-shore using any email (Iridium or maybe Winlink or SailMail). In fact, support for SailBlogs journals has been fully integrated into SailMail, so posting from offshore is dead simple.
When you are not offshore and have a more normal connection, the web interface is very friendly and easy to use. To set up a journal, you just register with the site, pick a template, and start adding posts. There are many other options as well to personalize your page, but you can add those as you get more comfortable with the system.
The tracking option will automatically build a web map for you, as well as generate a google earth feed for super-detailed tracking of your trip.
Accounts are free to set up, and there are three levels of premium membership after that. I would invite you to set up a free account and try it out, ask any questions you might have and then decide if the system might meet your needs (and I think it will).
You can also have a look at many of the other member's journals here:
http://www.sailblogs.com/member_list.php which should give you a pretty good idea of how sailors are using the system for their web site.
Thanks,
Tim
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tim harincar
tim at sailblogs dott com