Cuba...Private car hire

Depending on what you are looking for (a ride around town or a driver going outside the city), you can easily get cars at the Plaza De Armas - there is a circle drive in front of the fort there where they park. Someone will be in charge taking orders and assigning drivers. You can mostly select what you want (say a convertible). That is in Old Town. If elsewhere in the city you can make arrangements at major hotels or around Parc Central (plaza outside the National Theater). Drivers will wait where you are going if doing something round-trip. Negotiate all prices in advance.

If going outside the city, I'm not sure if the above will work or if it is better to work directly with a driver.

We had a loads of fun with Guillermo in his 57 Chevy. If the windows are rolled down so as not to asphyxiate (a common issue), the car seemed well maintained and operating pretty smoothly. He speaks English well and knows his way around the city (not always the case). I can give you his contact in in a PM if you wish.

Finally, while cars can be really hit or miss in quality and style and some drivers don't know their way around all that well, it is unlikely that you'd find anyone unreputable. Lesson #1 in Cuba: Just go with the flow.

Great. Thanks for the info Douglas.