What gets you on the plane: A no-hassle (read: no red tape) weekend in Santiago, Cuba’s second-largest city, with Insight Cuba, the outfitter that paved the way for U.S. tours in the country. Insight recently recently rolled out a four-day tour that covers a lot of historical ground: Expect meals at casas particulares (people’s homes) and visits to sites like the Moncada Barracks, where the Cuban Revolution began.
The happy surprise: Santiago is as culturally vibrant as Havana, with immigrants from Haiti, Jamaica, and Africa giving art and music an Afro-Cuban spin. Over the course of the weekend, you’ll visit a local art school and watch a steel drum band made up of former miners.
Weekend x factor: Santiago is just a one-hour flight from Miami, but getting to Cuba on your own still requires some legwork. Direct flights from the States are still restricted, but Insight will arrange your transport.