8 Steps to an 11th-hour Trip
1. Most airlines offer last-minute Internet weekend fares, usually on Wednesdays, which you can see by going to their Web sites or signing up for e-mail newsletters. Rather than cluttering your in-box, join smarterliving.com, which compiles all the week's deals in a single e-mail.
2. Keep an eye on the fares from week to week and you'll get a sense of who flies where and how often certain cities are on sale (Caracas is common, Rome is not). It's important to decide quickly, since these seats go fast, especially to popular destinations. If you're set on a particular location and it's not on sale, there's always Priceline.com, but you're playing with fire.
3. Don't be afraid of the phone. I tried booking my ticket through the new Orbitz.com Web site—a breeze to navigate—until it went buggy on me. Then I called US Airways and got it done quickly (and I didn't lose the Web-only fare). If the airline gives you attitude, tell them your computer broke.
4. Airlines often tag car-rental deals onto their last-minute e-fares—I got mine through Alamo, which partners with US Airways. Chain hotel specials are usually available, too.
5. Almost every hotel is on the Web these days, with pictures (even the dregsy Continental Inn, where I stayed, is shown on a Niagara Falls reservation site). City hotels that cater to business travelers are more likely to have last-minute deals, especially on weekends. Check out the consolidators—Hotel Reservations Network is one (hoteldiscount.com)—but know that you can sometimes get better rates by calling the hotel directly.
6. If you prefer package trips or just need inspiration, go to Site59.com. They can be funky—I once did a New York City trip called Beef and Guns, where I shot at a rifle range and then had a steak dinner—but there are plenty of more mainstream choices as well.
7. Visit travelandleisure.com for destination info (and sign up for the weekly Hot Deals e-mail of last-minute bargains). Then poke around: someone has almost certainly compiled a guide to anywhere you want to go. Citysearch.com has good, up-to-date listings for U.S. cities; Zagat.com is great for restaurant reviews. (I'm a fan of swimmersguide.com, which lists public-access pools all over the world.)
8. Don't worry. Any place you're likely to go has a tourism infrastructure and can handle whatever situation you bring to the table. Earlier this year, I bought a ticket to Madrid on a Wednesday and flew out Thursday night. On the plane I realized I had no idea how far the airport was from the hotel or how much the peseta was worth versus the dollar. But I figured it out. Remember, stupider people than you travel all the time, and do just fine.