It's official: Americans are finally welcome! But if you're seeking a Cuban adventure, you need the right outfitter who knows how to navigate a road map riddled with travel restrictions.
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After more than half a century of being off-limits to Americans (what missile crisis?), Cuba has quickly become the hot spot to visit. Just 90 miles off the coast of Florida, the communist country has many tour operators racing to fulfill U.S. regulations for travel. In 2011, President Barak Obama began easing tensions with Cuba by allowing “people-to-people” type trips. In January, he further opened the door to Cuba by adding 12 new categories—including religious, academic and humanitarian work—as authorized reasons to book a flight.
Tourism for tourism's sake—think sun, sand, and salsa—is not officially an option for Americans who want to discover this once-forbidden Caribbean gem. Some savvy travel companies, however, have found a loophole, offering government-approved cultural exchange activities couched in adventure.
Here are cinco ways to lawfully see Cuba for the first time. Make sure to pack your Mastercard: It's the only U.S. credit card accepted (since March 2015) in Cuba at the moment.
Explore Cuba by...kayak.
When it comes to Caribbean islands, it's hard to imagine anything other than its turquoise waters. On this eight-day paddling trip with Row Adventures, you'll get your fill of stunning sandy stretches and untouched coral reefs, but not at the cost of ignoring the country's beautiful forests and cities, too. This new people-to-people adventure, which debuts in November, combines sea, lake and river kayaking with hiking so that you can spend plenty of time in both its metropolitan and wildlife settings, including Havana, Bay of Pigs, and Zapata National Park (from $2995 per person includes guide, meals and accommodations, and activities; November through April; rowadventures.com).
Your morning bikecommute has got nothing on this cycling safari that will take you from the colorful capital of Havana to the majestic Sierra Maestra mountains to the beach breezes of the Varadero coastline. Touring the island with Black Tomato Cycling Excursions on this nine-day adventure is an excellent way to take in all the sights, sounds and smells that make up small and large Cuban communities. Make pit stops to chat with locals, sip on cafecitos, taste sugar cane at a plantation, take a dip in the playa, and learn to rumba to a live band (from $3,850 per person includes flights, accommodations and bike hire; January to April; blacktomato.com).
Slow your roll with Backroads to get a closer look at why world-renown poets, like Ernest Hemingway, called this magical place home. Walk three to five miles a day, getting to know this country, from its deep ties to baseball to how cigars are handmade at a local tobacco farm. When your feet get tired on this eight-day multisport trek, sit back in the saddle of a Trek bike and continue your journey with members from Cuba's National Cycling club, who will take you through forests, rural villages and quaint colonial towns (from $5,998 per person includes meals and accommodations, all activities, gear and guides; December though May; backroads.com).
Though the main island is the biggest in the Caribbean, it's not the only one that's Cuban. The country is actually an archipelago that includes the Isla de la Juventud and more than 1,000 coastal cays and islets. Hop on a yacht with Intrepid Travel's Cuba Sailing Adventures to discover the breathtaking, untouched islands of Cayo Guano, Cayo Largo, Cayo Cantiles and more. Occasionally throw yourself overboard with snorkel gear to come face-to-face with rich reefs and marine life, like sting rays and manta rays, in these crystal-clear waters. Back on land, sink your toes in sugar-white sands and snap selfies with resident iguanas (from $2075 per person includes meals, accommodations and domestic transportation; November through April; intrepidtravel.com).
Looking for a strictly cosmopolitan Cuban experience? Intrepid Travel has the urban adventure for you with its Best of Cuba time-warp trip that spans five colonial cities including Havana, Baracoa, Camaguey, Trinidad, and Santiago de Cuba. You have two full weeks to practice your high school Spanish while wandering (and hopefully getting lost) down cobblestone streets lined with fading facades that tell the rich, Instagram-worthy story of the country's revolutionary past (from $1930 per person includes some meals, all accommodations, domestic transportation, and activities; September through February; intrepidtravel.com).