We've been to Cuba about ten times over the years - Havana, Cienfeugos, Holguin, Guardalavaca, Jibacoa,Varadero, Santiago de Cuba, Santa Lucia. Both with kids and without. As early as 1995 and recently as last year.
In the earlier years Havana was an experience I looked forward to again but that was back when they used old Montreal buses for transportation (with original route names still on the front of the bus) and it was mandatory for vehicular traffic to pick up hitch hikers. Multiple families crammed into assigned housing in beautiful crumbling old mansions in Old Havana. And there was no convertible peso. It was certainly like being stuck in some kind of time. Now lots of Old Havana has been restored and all those families were kicked out. There is a tourist shop at the end of every street and gringo prices for everything.
Now unless you get off the beaten track you can get confused and think you're in Puerto Plata or Santo Domingo.
There are still many things that remind me its a communist country and subject to an embargo... sneaking to a black market dinner with a shower curtain for a table cloth, political slogans on crumbling walls and icy cold Old Milwakwee beer with a South American customs stamp on the bottom of the case at a beach bar... But those moments are watered down now. Or we're not as adventurous anymore.
I think pretty much every time we went there was an American or two at our Canadian departure point positioning for Cuba. The most recent was a man from Washington who came up to Edmonton to go to Havana for his semi annual visit to his wife. She'd just found out that they were being relocated from Havana to a small town inland and he anticipated a bit of a battle and friendly handshake to keep their housing assignment. As I recall she was a government worker.
Interesting place for sure but not much different than many parts of Dominican Republic. You have to go deep into the mountains or away from the main towns to get a different vibe.
All that said, we are planning one last trip to Havana before tourism picks up there.
Oh, and Havana accommodations are a bit worn. Cuban five star is North American three star, IMHO.
