Whether you're climbing Rainier with college buddies or joining an outfitted kayaking trip in Uruguay, scheduling an annual expedition is money in your sanity bank. No one knows how to do it better than Outside reconnaissance agent Mark Jenkins. His advice on how to make it happen:

Find the right partner: "Everybody will say, 'Great, amazing, I want to go'; 90 percent won't. Line up a number of potential partners and hope that one will come through. If they don't, go anyway."

Go where you want to go, period: "If this is your big escape, don't be cheap. Do what you want." Just be prepared to skimp on post-trip lattes.

Go long: "Two weeks is the minimum. Any less and your head will never really disconnect from the office."

Psych up your body and mind: "You will hate yourself if you're out of shape. Besides, training for a big trip is a way to get psyched." Ready your mind by studying up on the destination—read books, watch films, and peruse local Web sites.

Rent Globally
Renting a home away from home has become increasingly easy, thanks to the three biggest online resources, Rentalo.com, with 100,000-plus listings, and VRBO.com and HomeAway.com, both with more than 60,000. In addition to saving you money, house renting or swapping can plant you in otherwise remote parts of the world. Start by deciding what type of vacation you want, then do the following homework suggested by Susan Stellin, author of How to Travel Practically Anywhere (Houghton Mifflin).

Play the field: If looking to rent overseas, go through an agency unless you speak the language and know the area, advises Stellin. "You'll have the added security that somebody is standing behind the rental in case the electricity goes out."

Seek out word of mouth: For an unbiased review, ask someone who's been there, done that. If you don't know anyone who's rented a house in Croatia, toss out a question on a travel forum (thorntree.lonelyplanet.com, IgoUgo.com) to find an agency.

Get curious: Pepper your source with questions: What am I not seeing in these photos? Who can I call if I need help? "The more questions you ask, the better," says Stellin. "If you aren't getting the answers you want, it's a good reason to move on."