Hi Mdollar, I've PMd you with the contact details of the person I've booked through in the past.
I'm pleased you liked Santiago but it's a shame that you weren't able to stay over - it's a city that really comes to life after 10 at night. If you go back the person I've recommended to you in the PM has great contacts for Casas there - I've stayed in a different one every time and never been disappointed. And all within 10mis walk max of Parque Cespedes - the square bounded by the Casa Grande, Cathedral, Governor's House Museum and the Town Hall and hence within easy walking distance of all the good music venues.
And, yes, in answer to your question I have stayed in both Havana and Santiago but Santiago has always had the edge for me - and even more so these days because I know people there. I love the fact that one summer after a 2 year absence, sat on my own in a favourite haunt on my first evening in the city, I wasn't on my own for long as people I knew came in to say hello and join me in a drink as they spotted me through the window and I was then able to arrange my social diary for the rest of the week!
But it's also because Santiago has changed less as things have changed in Cuba over recent years. Havana is now much cleaner and sprucer as there is now more money around for restoration projects etc and the general population seems to have more money too. But it has also become much more touristy - larger and more numerous groups being herded around the main sights, more jinertero/as looking for an easy touch, fewer opportunities to meet with and be part of local life and, yes, noticeably more begging. In Havana it increasingly feels like I'm walking around a film set rather than a real living city unless you can get away from the main tourist drags. The small outdoor craft market has now disappeared and been replaced by a huge indoor one with too many stall all selling very similar stuff. Gosh, don't I sound like a real grump
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Especially since I still get a buzz from walking its streets and many of the changes that have happened have benefitted the locals which can only be good thing.
I love Santiago not just because does it now feels comfortably familiar to me but because it is a smaller, more accessible city where one can comfortably walk to most places and feel very safe as long as you remember to take the care that you would anywhere in the world, including at home, after dark. Also, the music and dance scene is not only so much better but the venues are more accessible to locals too than in Havana, even though still not that cheap by their standards. Many of the best music venues in Havana really are way out of the price range of most local people and it's a strange experience to be in Cuba listening to a Cuban band surrounded by non-Cubans apart from those who have had their entrance paid by visitors and who will therefore never ask another up to dance etc. It can be the same in somewhere like the Casa de Trove in Santiago of an evening when tourist groups doing the 2 day trip are bussed in but they tend to leave at 11ish (when the night is still often only really getting started!) but there are others where you feel that as a visitor you are still outnumbered by the locals and I like that.
No doubt as travel to Cuba and getting around the island becomes cheaper and easier for tourists then Santiago will change too but for the moment, for all its in places downright grubby, shabbiness it is still one of my favourite cities in Cuba. Havana and Trinidad have their attractions but Santiago has a heart and spirit that I don't think is found elsewhere and, yes, its central role in the story of the Revolution will always touch a chord with an aging hippy like me
SM