Flights
Hipmunk is awesome for investigating flight options. Only downside is that it doesn't include Southwest.
Best way to get a sweet deal on plane tickets: Date a flight attendant.
Tips on buying plane tickets at the right time:
The lowest price tends to hit between eight and two weeks before departure, but this rule fails during peak demand: Friday departures for spring break, and Sunday returns during the summer, Thanksgiving, and Christmas. For these, now is never too early.
At the end of holidays, there's usually a stampede to the airport. One more day with the in-laws can save you upwards of $100 — if you can stand it.
Flights on Friday, Saturday, and Sunday can easily cost $50 more than those midweek.
Price drops usually come early in the week. So a ticket bought on Saturday might be cheaper the next Tuesday. That's particularly true outside the summer rush, making fall the best time for a last-minute getaway.
If you want a summer vacation, domestic and Caribbean travel is cheaper to begin with and doesn't rise as high.
I don’t understand "aisle people." Gazing out the window is one of my favorite existential pastimes. I try to avoid having a seat directly over the wing by using a seat map finder.
If you’re on a long flight, and you're a professional basketball player with girlishly long legs like me, it’s also not a bad idea to check the seat map to see if you can get a seat with extra leg room.
Rather than trying to avoid layovers at all costs, remember that airports are some of the most interesting places on the planet.
Lodging
I haven’t used it, but if you’re price sensitive and not picky about hotels, Priceline Negotiator seems like a pretty sweet idea.
Hipmunk again for investigating hotel options. Holy crap I love this site. Kayak and TripAdvisor are also good options although with a far less amazing interface. Based on my recent NYC hotel search, Hipmunk was ideal for identifying locations within the city, and Kayak, Priceline, and TripAdvisor were better for finding deals. We ended up going with Priceline because with chopped fees it saved us about 20%.
Yapta is useful for tracking price drops. You can track prices for flights, too.
Before booking from a price comparison site, remember to check the pricing on the hotel/motel’s website.
If you’re adventurous (= non-prissy and non-risk-averse), CouchSurfing is awesome. I had great experiences in Alaska and Seattle.
Packing
If you are nervous about forgetting things, check out one of the many travelers’ checklists. Here’s one.
Bring comfy shoes. (I say that both seriously and ironically.)
Werner Herzog: "Sunglasses. Good boots. Binoculars. And a mosquito net."
I'd hate to travel without my pedometer. I love my fitbit. (Here’s my profile.)
Make sure you have plenty of clean undies and socks. Pack as lightly as possible on everything else.
Space is saved and wrinkles are limited by rolling up your clothes like a fruit roll-up.
Bring an audio recorder. Use it.
Doing
Keep your agenda as small as possible. Traveling done properly is not a checklist.
Wander around. Get lost. Find yourself. Repeat.
To avoid decision paralysis, alternate between who makes the decisions.
Make long stops. A rookie mistake of travelers is trying to actively “find” the city. It will come to you.
If you’ll be in the States, check Roadside America for amusing nearby attractions.
Use Tyler Cowen’s principles for choosing between dining options:
The better ethnic restaurants tend to have many of their kind in a given geographic area. Competition increases quality and lowers prices. The presence of many restaurants of a kind in an area creates a pool of educated consumers, trained workers and chefs, and ingredient supplies - all manifestations of increasing returns to scale.
The best ethnic restaurants are often found in suburban strip malls, where rents are lower and the degree of feasible experimentation is greater. Small and cheap ethnic restaurants are often better than large ones.
...And between menu options:
Ordering is often a more important decision than choosing the restaurant. Some rules of thumb, none of which are absolute:
1. Avoid dishes that are "ingredients-intensive." Raw ingredients in America - vegetables, butter, bread, meats, etc. - are below world standards. Even most underdeveloped countries have better raw ingredients than we do, at least if you have a U.S. income to spend there, and often even if one doesn't. Ordering the plain steak in Latin America may be a great idea, but it is usually a mistake in Northern Virginia. Opt for dishes with sauces and complex mixes of ingredients. Go for dishes that are "composition-intensive."
2. Appetizers often are better than main courses. Meals composed of appetizers and side dishes alone can be very satisfying. Thai and Lebanese restaurants provide the classic examples of this principle.
3. Avoid desserts. Most ethnic restaurants in America, no matter how good, usually fall flat with the desserts. Especially if the restaurant is Asian.
4. Order more than you plan to eat. Keep in mind that you are ordering for variety, not for quantity. You can always take the rest home.
I like Kevin Kelly’s suggestion about “Laser-Back Travel”:
When you arrive in a new country, immediately proceed to the farthest, most remote, most distant place you intend to reach during the trip. Then once you reach your furthest point, work your way slowly back to the big city (shown in yellow).
This American Life finds story ideas by asking natives, “Who’s the most interesting person in town?” Seems like a good strategy for traveling, too.
Ask a cab driver if you can ride around with him passenger side with no destination to speak of, just to accompany him on his shift.
Try to see the richest area and the poorest area, and the most industrial area and the most “creative” area.
Remember that there is much more to a place than the “sights.” There are also sounds, smells, tastes, and surfaces.
If it’s safe to, try to experience the city in the wee hours of the night/morning. Related: It helps to take mid-afternoon naps.
It gets tiring to be an endless explorer. Your curiosity quotient will inevitably drop. It’s perfectly okay to take breaks from traveling to do “normal” things like check your email.
The best way to finish a day is by writing about it.
You’ve had a complete trip if you’ve seen the inside of a library, a food market, a government office, a church, a convenience store, a sports arena, a bank, a hospital, a bar, a pharmacy, a brothel, and a private home. Four out of twelve ain’t bad either.
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What else?
