1. Decide where you want to go
"If you don't know where you're going, any road will take you there." Some clarity is important — at least the general direction, and hopefully the continent. What are your interests? There are literally thousands of activities and destinations to choose from. What gets you excited? A couple of years ago, on a flight back from Europe, I watched "The Bucket List," about two old guys dying of cancer who decide to spend their remaining days traveling the world doing everything on their list. What's on your bucket list? What would you be doing if you had two weeks to live?
2. Decide when you want to go
All of us are equally rich in time — the same 24-hour day, 7-day week — but here in America, time off seems to be at a premium. Hard to believe the world will keep turning without you, but trust me, it will. No one on their deathbed ever asked for one more day at the office, so take as much time as you can. Travel season is divided into roughly three seasons: low season (traditionally November 1 through March 31) when prices are rock-bottom and the weather is cooler; high season (June, July and August) when the kids are out of school, the weather is hot and prices are highest; and shoulder season (April/May and September/October) — the best time, when prices are low, the crowds are gone and the weather is still nice. One other peak time is the Christmas/New Year holidays. Thanksgiving is a good time to go, because no one besides us celebrates it.
3. Map out an itinerary
You'll need a start date and an end date, and hopefully as many days in between as you can squeeze out. Decide which city you're flying into and out of — usually the same city, but "open-jaw" tickets are an option too. Book at least the first couple of nights and the last night, as you'll need the rest.
4. Call your travel agent!
By booking the air plus at least a couple of nights' hotel, you can book through a tour operator, get discounted airfares and hotels, and reserve it with a small deposit. What are you waiting for?
Stay tuned for Part II.
