The Westfjords of Iceland
The Westfjords are difficult to get to. The roads are windy, mountainous, often unpaved, and they seem to go on forever. As a result many travelers skip the area entirely. But if you enjoy stunning vistas, jaw dropping fjords, and getting off the beaten path, the extra time is well worth it. After all, it's all about the journey and not the destination... but the Westfjord's destinations are pretty damn cool, too (pictured above: panoramic morning view of Ísafjörður).
Purto Natales, Chile
Primarily a transport town, Puerto Natales funnels tourists on the way to somewhere else. Visitors tend to spend just a short night there, if they stop at all. But it'd be a mistake to leave so soon. The seafood dishes are amazing, and the town's vibe is welcoming and super laid back. And the scenery? Ahhh-mazing.
Another transport hub, Chennai is often overlooked as a destination in and of itself. You only need a day or two to see the big sights, and it's well worth it. As an added bonus, Chennai has some of the friendliest people I met in India.
Listvyanka, Siberian Russia
Throughout history, hardly anyone has willingly traveled to Siberia. But you should. It's awesome. For more on Siberia, read this: Why Would You Want to Travel HERE?
Not so much underrated as it is simply overlooked, Sri Lanka is more than worth your time. For one, it's massively inexpensive. We're talking a double hotel room on the beach for $9 USD a night. The spicy South Asian street food is delicious, and the beaches are more than adequate to lose yourself for a week or more. When you're tired of the waves (if that's even possible) head inland for some culture. Don't miss the hike to the top of Adam's Peak, best done at night for a gorgeous sunrise view.
Kuala Lumpur, Malaysia
Southeast Asia's travelers usually traverse either Bangkok or Singapore Airports, but give Kuala Lumpur a look next time you're there. The markets are just as good, and the vibe is less seedy than Thailand's crazy capitol but edgier than boring Singapore.
Mongolia doesn't tend to rank terribly high on anybody's travel list, but it should. If you like exploring vast open spaces and fascinating nomadic cultures you'll love Mongolia. Make sure to spend a few days in the capitol city of Ulaanbaatar.
Tokyo's Golden Gai District
Head down the back alleys of Tokyo's Shinjuku neighborhood for a slice of old school Japan right in the center of one of the most modern cities on the planet. The quaint alleys appear dark and unwelcoming at first glance. But go on a little further and you'll soon realize those alleys are lined with small bars, each seating only a handful of people. Not all are entirely receptive to foreigners, so use discretion. But find a good one and you're in for a fun night of local culture and conversation in an intimate and cozy setting.