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First, the easiest way to save on baggage fees is to take everything in a carry-on and don't check any bags.
This works for a quick getaway, but I'd have a hard time managing a week's vacation with only one small bag! And I have to admit a pet peeve - I hate waiting half an hour to exit the plane because everyone is wrestling their bags out of the overhead compartment. (I've been guilty of it myself, but I'd rather pay a few bucks to check my bag and have just what I need on the plane).
Remember, too, the restrictions of what can be placed in your carry-on, and during "high alert" periods, there are even more restrictions - it's almost impossible to keep up with it!
Southwest Airlines does not charge baggage fees, so that's a good option if possible (being a smaller airline, they don't go everywhere, and you can't choose your seats).
I try to check only one bag, at least when I'm heading to my destination. I always bring a roomy, zippered tote for souvenirs, etc, which may be checked or carried on, depending on what I need to do on the return trip.
And I always try to check in online the day before the flight. Not only can you print your boarding pass and get through the lines a bit more quickly, you save a little bit on the baggage fees (usually $5 a bag less than checking them when you arrive at the airport).
