Find the Hidden Deals

9. Sign up for e-mail notifications. The best airfare and hotel sales are largely unannounced. Airlines and hotel companies target specific subsets of travelers—loyalty program members, holders of certain credit cards, people who've registered on their Web sites—and alert them by e-mail. To keep your in-box from being bombarded, get a dedicated e-mail address for such alerts and check it when you're ready to start planning your next trip. If you can make quick purchasing decisions, sign up for alerts from flash-sale sites that sell hotel rooms at discounts of 40 percent or more, such as Jetsetter and Tablet Hotels.

10. Carry credit cards that earn you elite status. Play your travel-rewards credit cards right and you'll receive special rates and perks. Carry one airline-branded card and one hotel-branded card that help you attain and maintain elite status—and make sure that at least one of those cards charges no foreign-purchase fee (preferably a Visa or MasterCard, since those are more widely accepted overseas than American Express).

11. Lock in business-class bargains from Etravelbid.com. Etravelbid.com negotiates unpublished, discounted business-class fares with no advance-purchase requirement. In November, snag a last-minute flight from New York, Boston, or Chicago to Dublin for $2,300; from Miami to Berlin for about the same; or from New York to Hong Kong, via Seoul, in the upstairs business-class cabin of an A380, for $4,500 (prices include all taxes and fees).

12. Find mileage-award seats on routes that connect airline alliances' hubs. Competitours founder and CEO Steve Belkin taught me this one: Suppose you need to fly from Cleveland to Venice. Don't bother asking if there are award seats available on that route; there won't be. Instead, start with the hub-to-hub routes flown by the carriers in your alliance. Say it's the Star Alliance: Look for availability on flights to Frankfurt, Vienna, Munich, or Copenhagen from Chicago, Newark, Philadelphia, Toronto, or Washington, D.C. (hubs for Star Alliance partners Continental, United, US Airways, and Air Canada). That gives you more than 20 possibilities. Once you've found a hub-to-hub flight with award seats, tack the short-haul flights on either end.

Use the Right Online Tools

13. Find the most flight choices with ITASoftware.com. This site provides perhaps the most comprehensive and least biased fare and route options. Use it to learn which airline offers the most suitable itinerary, then go to that airline's Web site to book. If your schedule is flexible, choose "See Calendar of Lowest Fares," punch in a monthlong travel window and the length of the trip, and the search engine will tell you when to fly.

14. Sign up for airfare alerts. AirfareWatchdog.com finds unadvertised low fares that other search engines miss—and notifies you daily via newsletter or immediately via Twitter. FareCompare.com alerts you when a fare drops by an amount you've specified (say, $50). Both help suss out connecting flights that can save you hundreds of dollars. AirfareWatchdog's "To a City" alerts list fares from various airports to your destination. Say you want to fly from Houston to Kona, Hawaii. The Houston–Kona fare might be $800, whereas the Dallas–Kona one might be $350. If you'd signed up to see all the fares to Kona, you'd know to combine the Dallas–Kona fare with a cheap Houston–Dallas ticket. As for FareCompare, sign up for alerts to Kona not only from Houston but also from hubs west of it like Los Angeles and San Francisco. If you find a deal saving you $500 from one of those hubs, find a way to get there from Houston.

15. Get seat alerts from ExpertFlyer.com. If you don't want to return to an airline's site repeatedly to check whether a better seat has opened up, consider paying $5 per month for an ExpertFlyer membership. Punch in the flight you're on, and the seat type (e.g., aisle) or rows you want, and you'll be alerted by e-mail if any of those seats become available. You can also receive alerts on the availability of mileage-award seats and upgrades.

16. Get a better seat with SeatGuru.com and SeatExpert.com. Don't select a seat without typing the airline and flight number into these sites and checking your location. If you must accept an inferior seat, return to the carrier's site before your flight to see whether a better one has opened up. When you check in online, do so as early as possible; you'll often find that seats have become available. And when you're choosing airlines, use SeatGuru's "comparison charts" to snag comfier seats and better in-flight entertainment.

17. Use TripAdvisor to connect with a hotel's general manager. Often a general manager will reply to critiques of his property on TripAdvisor. When you book a room, read the replies, note his e-mail address, and write to him saying that you admire how he's replying to reviews and that you're looking forward to staying at his hotel on X date. He'll appreciate your kind words, assume you may be a frequent reviewer, and hopefully do something extra for you during your stay.

18. Keep your miles from expiring with AwardWallet.com. Nothing's worse than a big stash of miles that's just vaporized. AwardWallet shows you all your different mileage accounts at a glance, including expiration dates, so you can take action to keep miles and points from expiring. I use it to track the accounts of everyone in my family: Within seconds I can see whose miles are in danger of expiring or who has enough for a trip, so I can cash in before they devalue.