Figure out where you want to go. Flexibility is key. Rather than pigeon-hole your plans to Aruba, for example, be open to any beach location in the Caribbean. Or rather than just Las Vegas, maybe consider Reno or Atlantic City.
Decide on a budget. You should come up with a budget ahead of time. Give yourself a little flexibility, but figure out what you can afford and stick to it. Vacations aren't any fun if you have to worry about money the whole time.
Search the sites. There are a number of sites that are excellent for searching for good deals. Search them all. Some of my favorite sites include Hotwire, Orbitz, Travelocity, Kayak, and Last Minute Travel. I also like Travel Zoo because it gives you the option to search multiple sites.
Check regional airlines. Many times, regional airlines are not listed on the major travel sites. For example, Southwest has some of the best deals in the industry, but you won't find them listed on travel sites. The best way to find which airlines service your local airport or the surrounding airports is to go to the individual airport Web sites and find the listing of airlines it services. Once you have your list, go to the individual sites and search for flights from there.
Consider your accommodations. After you've booked your flight, you'll need to find a place to stay. One of the best pieces of advice I ever received was to look into bed and breakfasts. Sometimes, they have the best deals. Also, with B&Bs, you will often get extra amenities such as a bottle of wine, a full breakfast, or a hot tub.
Book your travel and have fun!!
