Why it’s so cheap: Like shoppers waiting for Target to open on Black Friday, US airlines poured into Cuba as soon as travel restrictions were lifted in 2016. This of course has led to fierce competition and some of the cheapest flights in the Caribbean. Cruise lines have also made Cuba a regular stop on short itineraries, making the island easy and affordable to reach.
Why you should go this year: If you went to Cuba before 2016, you remember how it seemed like a time warp, untouched by American influence since the 1960s. Now tour buses pack the narrow streets, and guided groups meander through the Spanish-colonial architecture. It’s not a full-on tourist trap yet, but it’s on its way. There is, of course, also the issue of a shifting political climate that may increase restrictions on travel to Cuba. It’s not hard to get there now, but nothing is guaranteed. For a low-cost cultural trip to one of the most photogenic places in the Western Hemisphere, you’ve got no better option.