Planning a vacation in 2010 is a lot different than planning a vacation was in 2000, or hell, even 2009. It used to be you had to buy those big paper maps you could never quite fold, buy a couple heavy guidebooks to throw in your pack, and basically have everything planned in advance.
On our most recent family vacation, I decided to try to make it work with only a mobile phone. Well, two mobile phones, actually: an iPhone and a Nexus One. Here's what worked, and here's where the plan fell short.
Old way: Before leaving for vacation - enter all driving routes into Google Maps or (gasp!) MapQuest, print out and bring with you
Last Year: Rent a Neverlost from Hertz
This Year: Do a search from the iPhone Maps application or the Car Home application on the Nexus One. I must say, the driving directions on the Nexus One are pretty fantastic - and pretty equivalent to an in car GPS system.
Where it fell short: Automated directions aren't always the best. In LA, the directions had us getting off the freeway in Compton and driving to another freeway, when eyeballing the map showed the two freeways had an interchange.
Finding a Restaurant
Old Way: Look up places to eat in a big old paper guidebook like Fodor's or Access. If you were lucky they were still in business. When coming from the hotel ask the concierge, which is always a good idea anyway unless they direct you down the hall to the hotel restaurant.
Last Year: Do a Google search on your mobile phone which didn't have mobile optimized landing pages
This Year: Yelp. Either the iPhone app or on the mobile browser. Hit the "Nearby" button, read reviews, and use the Map pane to see how to get there. Yelp has enough critical mass to really work pretty much anywhere I've been, and the places that are rated well do turn out to be great choices. Then make a reservation with the Opentable iPhone app. You could skip using Yelp and just use Opentable, but I don't find the reviews to be at critical mass for usefulness with Opentable alone yet.
Where it fell short: It didn't. At least in the US. In Europe, we used qype.com, which has a Qype Radar iPhone app. Make sure you change the language to the local language to see reviews, though.
General Itinerary Information
Old Way: Print and fold.
Last Year: Search Gmail for your itineraries.
This Year: Forward your Gmail confirmations to TripIt and use the TripIt iPhone App. Trip it has figured out how to parse most travel email confirmations such that they can easily aggregate a travel itinerary for you. This service is highly recommended.
Where it fell short: There's no app that can replace tipping the skycap so he gives you the shortcut through security with kids.
I'm not much of a planner, so I like where it's all headed.