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Thinking of doing a last minute 1 weeker to cuba in November. Interested in spending time in Trinidad and Havana and possibly Vinales though not sure if there is time for 3 places in 7 days. I'm a 50 year single male on my own and I'm really just looking to get away for a week, drink coffee in the morning, see some sites and enjoy a cold beer in the evening, possibly seeing some live music and practicing my spanish here and there.
I plan to stay at casa particulars along the way. Likely I'll fly into Santa Clara as the flight prices are the cheapest, but possibly Cienfuegos?
Should I book Casas in advance or just look for something upon arrival I don't mind winging it. As a single guy am I likely to get hassled by women looking to "earn" money. While I certainly wouldn't mind meeting nice women, I'm definitely not into the "pay for play" scene. Trinidad vs Vinales in a question of taste.
Vinales is more for nature, site seing, etc. Trinidad is more for town, music, ambiance. You will have no problem finding casas in November. Make a preselection with the help of the comments on TA, on internet or in a guidebook so you have adresses to go to when you arrive. If you follow one of the many husslers who will be waiting for you at the bus terminal if you travel by bus , the price will be higher since they get a commission.
Don't let any hussler follow you or escort you to a casa you picked, because he will get the commission even if did not do anything for you. Yes, you will. And not only by women and man offering women openly for a price, but also by women who will make you believe they like you, want to be with you and will then get gifts, possibly money, and if they are really lucky a marriage proposal and eventually a visa out of Cuba Santa Clara is really not convenient for Trinidad 3h or Habana 4h.