Winner: Cuenca, Ecuador
This Andean town of 330,000, located 270 miles south of Quito, looks like a sleepy colonial city, but it’s the gateway to a massive pile of fun. Cojitambo, 20 miles north, has more than 160 rock-climbing routes, from traditional lines to sporty 5.14’s on 500-foot-high volcanic walls. Cuenca itself has Class II floating along the Tomebamba River through downtown, and nearby Cajas has trails, like the six-mile Parada Patul, that climb to nearly 14,000 feet. Go with South Expeditions (from $1,693 for three days; ) or DIY and stay at Hacienda Caballo Campana (from $98; ), where you can hike, bike, and horseback-ride over the Yanuncay River—all just 15 minutes from the city center.
Runner-Up: Pahoa, Hawaii
When you go to Hawaii, you expect great access and a mellow vibe. It doesn’t get much more chill than Pahoa, a town of under a thousand people near the eastern point of the Big Island. Stay at Hale Moana (from $220; ), and set out to explore black-sand beaches and volcanic caves, hike to burbling lava and geothermal pools, or snorkel with sea turtles and dolphins—often before your first bite of morning mango. Arrange everything from surfing to mountain biking with Island Jane Eco-Tours ().