PART ONE: TRIP PLANNING
The best advice is lots of advice
Clip any newspaper and magazine articles. E-mail friends, friends of friends, and even like-minded strangers (via message boards) for advice. Ask for tips from bloggers who specialize in destinations. Check out user-review websites like TripAdvisor. Don't rely on any single source, even Budget Travel; look for a consensus.
Flexibility pays off
When it comes to booking a flight, being flexible with dates used to mean doing a lot of data entry. Flexible-date searches at Travelocity, Kayak, and many airline sites now make it a snap to see how much you'll save by changing your dates.
Think outside the hotel-room box
Renting a house, condo, or apartment--or swapping homes--may be better, especially for groups. The Internet has made locating such non-hotel options a million times easier. Three vacation-rental websites: VRBO.com, HomeAway.com, VillasIntl.com. Three home-swapping websites: HomeExchange.com, HomeLink.org, Intervac.com.
Someone has to pay the tennis pro's salary
When you stay at a hotel, you're essentially paying for all the services offered--gym, water sports, concierge, tennis courts--even if you never use them. So figure out what's important to you, and what you can do without.
Pick the right guidebook
Browse to check that the research isn't stale and that you trust the writer's sensibility. Time Out is reliable for big cities, and Lonely Planet is still best for off-the-grid trips.
Call a travel agent when you're...
Planning a complicated trip, traveling with a large group, going on a cruise, hoping for advice on the destination. Always ask: Has the agent been there?
Scout from above
Use Google Earth's cool satellite images to gauge the exact distance between the hotel you're considering and the beach, a highway, the Eiffel Tower, the subway, Chernobyl....
The best price is out there somewhere
And there's no one simple way to track it down. Start with meta-search engines like Kayak and SideStep, which scour multiple sites for flights, hotels, cruises, and car rentals. Orbitz, Travelocity, and Expedia are good for getting a feel for what's out there--though they often don't search all airlines, and they tack on service fees.
Think like a bloodhound: Prices for car rentals and hotels fluctuate, so never give up sniffing out a better deal. When you locate one, snap it up--and cancel the old reservation. Just make sure the cancellation policy won't bite you in the rear.
Call hotels directly
Certain special rates are only sold over the phone; others are only sold online. Note: Cancellation policies for these can be strict.
Know thy neighbors
For cruises, tours, and other group experiences, ask who'll be joining you--how mature they are or aren't, whether everyone will already know each other, and so on. For hotels and resorts, make sure there's not a wedding or a convention during your dates. For cruises, check out CruiseCritic.com.
Why packages can be major bargains
To fill rooms and seats, hotels and airlines will resort to rock-bottom prices. For obvious reasons, they don't like to publicize these rates, so they sell a certain number of rooms or seats to companies that bundle them in packages. That way, no one knows exactly what the airfare or hotel alone costs. Here are a few things to bear in mind before you buy a package:
1. The only way to know if it's a deal is to see what it costs to book separately.
2. Don't trust the packager's hotel description or star rating; research the hotel on your own. If you don't like the hotel being offered, you can usually upgrade.
3. Ask about the flight's times, connections, airline, and change and cancellation policies.
4. Extra nights are often available at a ridiculously low rate.
Get and fill prescriptions for sleeping pills and medicine for traveler's diarrhea. At some point in your travels, you'll be extremely relieved that you did.
Silverjet! Eurofly! Zoom!
It seems like there's a new airline every day, and because they don't show up in booking engines, figuring out who flies where is a headache. Bookmark DoHop.com--it lists which carriers serve an area.
Third-party bookers often get second-class treatment
Wrong as it is, hotels are nicer to guests who seek them out than to those who come via a third-party booking engine. Whenever possible, book directly. If you see a low rate elsewhere, ask the hotel to match it. Hotels will almost always undercut any middleman--which isn't all that difficult, when you consider that booking engines tack on fees
In case of emergency
Old rule: Bring a photocopy of your passport with you. New rule: Scan your passport and e-mail it (and your itinerary) to yourself and to someone you trust back home.
So much for Tuesday after midnight
For years, many "travel experts" have theorized that some or other weeknight was when airlines released fantastic deals, but that's hogwash.
"Garden-view" equals parking lot
Words can lose their meaning (if they ever had much of one in the first place), and you can't assume your definition is the same as someone else's. A few words and phrases you should cast a gimlet eye on: boutique (when describing hotels), centrally located, charming, chic, garden-view, low-fare (for airlines), luxury, quaint, recently renovated, romantic, stylish, suite, villa, walking distance. Plus: Hotel rating systems aren't worth a whole lot. What makes a hotel four-star versus three-star can be something as silly as a phone in the bathroom.
The proof is in the picture
If a hotel or condo doesn't post photos on its site, ask for images to be e-mailed. But don't assume photos are entirely trustworthy. Images shot with fish-eye lenses make rooms seem bigger than they are; or the hotel may send a photo of a room that's better than the one you reserved.