Welcome to nonrevving. As far as traveling over a holiday weekend it can be very risky. Especially if you don't have very much seniority. I wouldn't throw out all of your plans just yet though. Usually if you travel on the holiday, ie. Christmas or new Years, you can get where ever you want to even though you might not make it a couple of days prior or following a holiday. Another thing to consider international. It won't be Presidents Day in Europe. You will probably have a better chance flying Business class to Rome then you will flying coach to Florida or a ski destination.

As it has been suggested plan for an extra day or two if you can. On top of this I always find coworkers who are willing to pick up for me if I get stuck and I in turn do the same for them. You never know when weather is going to strike and problems on the East Coast can create Problems on the West Coast.

As it has been suggested always research what other options you may have in case plan A fails. Zed fares on other carriers are great but in some instances an ID90 could save you quite a bit. You need to become very familiar with your carriers ticketing agreements with other airlines. Always do this before you leave.

There are a lot of people in this industry who will tell you that what you want to do cannot be done. I took 11 people to Hawaii in November. The return flights were full and everyone thought I was nuts. Our trip was to be 10 days long and then I planned an extra four days off just in case we didn't make it. I took 3 home early and then the day we planned to come home I put my wife and 2 of my kids on a nonstop flight home on another carrier. The rest of us flew with no problem on Continental on the flights we preferred.

Anyways have fun with it and don't let one bad experience put a damper on your travels.