Island Hop by Bicycle in Scotland's Outer Hebrides
The Trip: This 174-mile guided mountain-bike ride along the Hebridean Trail with Wilderness Scotland weaves its way across seven islands in a weeklong adventure off the remote northwest tip of the U.K. Blazed in 2012, the trail follows ancient wilderness paths and rolls into little villages where proud Gaelic-speaking islanders live steeped in tradition. You'll see the Callanish Stones, a prehistoric Stonehenge-like grouping of rock monoliths. You'll ride up to six hours a day for a week, hopping islands with your bike on a rigid inflatable boat. Post-pedal pints are part of the daily ritual.
How It's Life-Changing: The first couple of days can be a shock for leg muscles, but soon you realize you're no longer constantly watching for the support van to show up for a snack break. You've got this. Finishing it is a huge achievement that you owe to the cleansing island air, mesmerizing views, and camaraderie among riders.