There's no mystery to me. Roth was a regular visitor to Cuba. It seems to me that the meeting was held on the balcony of Roth's hotel/casino which was probably one of the ones that he said would be turned over to others after his death. He would have had a regular suite there.

You really don't think that Michael, the most powerful Don in America, is simply going to grab a taxi at the airport like any tourist. Ola was his escort and guide since Ola knew his way around Cuba physically and politically.