Best Midlife-Crisis Trips

Climbing Mount Kilimanjaro, Tanzania

Why Go Now: The trip can last anywhere from one to three weeks and include five to eight days of climbing, depending on how fast you want to ascend. An immense physical challenge—Boston attorney Jane Goldstein prepared by running up bleachers at her local high school with a backpack full of law books—scaling Kilimanjaro with a group of like-minded travelers creates new bonds and a heightened appreciation of nature. Reaching the summit isn’t even necessary; most hikers say the deepest change happens on the way there.

Go with: Mountain Madness.