I recently learned that an old friend of ours spends several months of every winter in Havana, Cuba. She stays in a B&B in La Habana Vieja, just four blocks from the great jazz club we found.
I asked what it costs her for accommodation and she told me she has stayed with the same family for so many winters she gets a rate that we would not be able to get but that generally, places are available in the $300 – $400 per month range (and up). She can eat as many meals per day with the family as she wants and many reasonable restaurants are nearby. The beaches are a short bus ride away. Canadians can stay in Cuba for up to six months per year with no Visa or immigration concerns.
Cuba now insists that visitors have medical insurance for the length of their visit and this is evidently available at the airport for about $1 per day.
I am getting interested! Not for this year but maybe next….