After flying from Miami to Havana, you'll spend two nights in the Cuban capitol smoking an inordinate number of cigars before boarding the S/C Panorama, a triple-masted mega-yacht that holds up to 49 passengers and 18 crew members. From there, you'll set sail for Cabo San Antonio, the mangrove-covered island of Cayo Largo, the Spanish colonial town of Trinidad, and finally Cienfuegos, "the Pearl of the South"; all the while stopping at coffee plantations, museums, and a UNESCO–designated Biosphere Reserve, not to mention a Sea Turtle Breeding Center along the way.
Cuban experts and interpreters will also be on-hand to help/force you to have meaningful interactions with locals and culturally immerse yourself -- no really, it’s required. It's not called a "People-to-People" exchange for nothing.
So, what's all that small talk gonna set you back? About $4,490 (including airfare), to be exact. Get more details and book your trip, right here.
Sophie-Claire Hoeller is Thrillist's über-efficient German associate travel editor, and remembers her mom registering for a Cuban cell phone for the guide. Follow her @Sohostyle