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With every post, Kiona, creator of the popular blog and Instagram account How Not to Travel Like a Basic Bitch, is teaching herself and her followers how to be, well, less basic

As we wait to see when we'll be traveling again, these apps can help you to save for your next adventure

With so much funding from the government going toward boxing and baseball, it's much harder to find surf gear

Three paddlers sail to Havana in order to kayak 27 hours all the way back to Key West, Florida

Professional boxing has been illegal in Cuba for more than 50 years. That hasn't stopped the country from producing the best fighters in the world.

La Ruta Mala is a Cuban bikepacking trail whose name translates into ‘the bad way’

Melissa Cristina Márquez tells Outside about her experience filming ‘Cuba's Secret Shark Lair’ for Discovery Channel’s Shark Week

Let's make "I'm from America" great again

Surfing in Cuba is a legal gray area; it's illegal however very loosely enforced. As their government strives to stabilize, a few surfers are making their case to compete in the 2020 Olympics.

When Caspar Schaede left for Cuba to film, La Obra, he wasn't expecting to experience the wonderful hospitality that was offered to him. This film is an attempt to summarize what he learned and explored; though for him, it still feels rough and imperfect.

Explore: Chapter Three is a short film from Tyler Allyn and Cooper Lambla that follows a group of friends as they embark on a bike trip across Cuba

From epic skiing in Antarctica to a lazy beer-fueled canoe trip in North Carolina, these are the best places to visit this year

The year ahead will be filled with goggles that guide us down the ski hill, stoves that could save humanity, and Kubrickian pods that will carry us to the edge of space

With Airbnb and Yelp already operating in Cuba's capital, will hordes of American tourists sipping McDaiquiris ruin the very authenticity that draws us to the rebel island nation? Allow us to explain why you should go now—before Cuba changes, while it changes, and because you will change it yourself.

But sometimes the best way to restore diplomatic relations is a little friendly competition—and plenty of rum

Don't plan any vacations before reading this year's Best of Travel winners.

Most Travelers aren't directly affected by the resumption of U.S.-Cuba diplomatic relations.

Cuba. Where travelers lounge on picturesque beaches, swirl mojitos, dance til sunrise, and cruise back to their hotels in ’57 T-birds. Travelers, yes. But Americans, no. Until 2011, these indulgences were long off limits to U.S. citizens due to a Bay of Pigs–era trade embargo.  But despite the Obama Administration…

Tour companies are offering new and unique ways to explore formerly forbidden countries. So what's the catch?

In a country where a sport that has always represented social rebellion was unlikely to ever be tolerated, a small group of skaters created their own gear with whatever materials they could find—and started a revolution

Get your life list out—here are some of our all-time favorites

Start off 2012 right, with a trip to one of the world’s wildest destinations

Why hordes of Yankee travelers are exactly what the island needs.

North of Havana is a fantasy world of mangrove-lined cays and green water flashing with tropical fish—perfect sea-kayaking country. But the line between what's permissible and what's not in Castro's kingdom falls in a gray area, and comings and goings by water always mean trouble.

On a bicycle tour of Cuba, solidarity can only take you so far.