Floor Pump - get a good one from a bike shop (REI, performance, wherever) I have a Joe Blow and am happy with it. I really like the ones with the dual head that will either do presta or shraeder without having to change anything. If you have a cruiser that you've been filling up at the gas station, and just got a road bike, I wouldn't be surprised if your bikes have different valves. If your new bike has presta, you'll have to get a presta head.
On the bike - a road morph. they are wonderful little pumps.
http://www.rei.com/product/648089/to...ump-with-gauge

I've always been told to never use car pumps - I think because of the danger of over-inflating.