Back before I knew better, I did an unsupported, off-the-grid ride in West Maui. A local bike shop spoke of backcountry bliss — no cars or tourists, only mountain vistas, farmland, and the Pacific Ocean. It was beautiful, but not a place you want to run out of food and water on a 100-degree day. Cranking up a steep climb, I began to feel lightheaded when a bright green sign appeared. Julia's Best Banana Bread on the Planet, 3 miles ahead. I got lucky that time, but my lack of planning could have ruined the entire vacation. So instead of blindly hitting the road and hoping for the best, here are the essential tips you need — from renting and packing a bike to finding the best routes — to travel smarter and make the most of your next self-guided getaway on two wheels.