Viewing your posts as a route plotted on a Google map is simple with this plugin. Just add the shortcode [logmytripmap] to a page to see the map.
You can upload your pictures using WordPress for iPhone, Android, Blackberry or Nokia. Geolocate your post using these apps and then it will show up on a LogMyTrip map.
It does on the http://www.LogMyTrip.co.uk site, but not using the plugin alone.
It's only one trip per user, but it's easy to create an additional user using an alternative email address, then use it to create another trip.
The LogMyTrip plugin works with, but does not require, the Geolocation plugin.
This plugin plots ALL posts that have associated geolocation information in date order for the default (post_author = 1) user. Points without geolocation data, or for other users, will not be plotted. However, you can switch to a different user by creating a cookie called 'tid' on the root of your site with a value equal to the ID required; e.g. Cookie: tid=4 for post_author 4.