After having written a half dozen of these web travelogs, I seem to have settled on a system and style that supports the things I find I need. I have a web server on my laptop so that I can run the web reading/writing system even when we are totally disconnected from the Internet.
At the core of the "system" is a wiki -- a web that can be edited in the browser directly from the page you are viewing. A wiki is really just a system for managing the content on pages (keeping one page separate from another, being able to remember changes to pages so that you can roll back to a previous version, etc.) There are many implementations of wikis -- I use PmWiki, a wiki that is particularly suited to people like me who like to extend basic systems with macros of high level operations. I have extended PmWiki so that it supports the needs of a travelog writer. For example, there is a single command for including an image with a caption. The command:
(:image dreams.jpg title='Field of Dreams' width=240:)
results in the thumbnail for an image with a caption:
If you click on the thumbnail, then a larger version of the image is shown, framed with the caption and a control for getting back to the original page. This macro operation
(:image ... :) is one of the extensions I developed for my travelogues.