Why you should go: Umm… because we can? No, but seriously. Because we can, at last. While it’s easier than ever now to get to Cuba from the States (six airlines have announced direct US flights to Havana in 2016), there are still some caveats. Travel to Cuba is legal without a license or paperwork so long as the purpose of travel fits into one of 12 categories: education; religious activities; support for the Cuban people; humanitarian projects; research; journalism, et al. If your travel falls into these categories, just organize what is called a “people-to-people” exchange, in which you’re meaningfully interacting with locals. This could be visits to art galleries, an educational session with a historian, a city tour. Get creative, confirm an itinerary, print it out, and you’ll be on your way.
Why you should go right now: We’re still at the front edge of a guaranteed sea change, as Americans start making their weekend jaunts for surfing and cigars. The US hotelier Starwood recently opened a Four Points by Sheraton in Havana. And this is only the beginning. That charming “preserved-in-time” destination we’ve all heard of is about to get brought up to speed on the 21st century in a hurry.