Thanks to Debra for recommending TripWiser's "Road Tripper 2.0". I've sampled the program to plan our road trip that we're scheduling sometime in October for 14 days. Starting off from Boston to visit P and M, to Colorado to visit the wolf's. We're also planning additional destinations such as Ohio and California to visit other friends, but that's still tentative.

Unfortunately, since it is still in it's Beta stage, not much information from road trippers are available, at least to the destinations that I specified. The Road Tripper actually helps you plan your Trip, more of like an organizer. It's main functions are:

1. Plan your itinerary. Schedule from Day 1 up to the last day. Add activities, hotels and restaurants.

2. Provides satellite and hybrid maps of your destination. If you click the red diamond, suggestions such as Things to Do, Accommodations, and Restaurants. It provides suggestions on places to go to and exact addresses for restaurants.

3. Trip route is also provided.

4. The option to upload pictures via Flickr.

Although I didn't try asking for help, Live Help via Meebo is also available.