Escorted Tour of Cuba
I spent roughly three weeks in Cuba and I don't think I would have got half as much out of it if it wasn't for doing an escorted tour for the first half - with additional free time added on at the end which we spent in Varadero. I have blogged extensively about each element of the trip. Virgin Holidays "Cuban Experience" tour was the one we went with in late January this year - it's probably not ideal if you're trying to travel on a small budget, but given how unique and vast Cuba is, it seemed like it would be worth digging a bit deeper for the convenience and reassurance of this type of package. https://cherrylsblog.com/2018/02/21/why-you-should-try-a-touring-holiday-cuba/
The tour took us out to one of the Cayo off Islands (Cayo Esenachos) which was absolutely breathtaking, and having a local guide with us each day mean't we had access to a fountain of knowledge on tap.
The only downsides to this tour - is that you will be up early each morning and on the road a lot, living out of suitcases as you travel from one region and hotel to another throughout the tour. This is why we added another 10 nights on at the end and chose to spend that time in Varadero on a beach resort - but you could spend it wherever you like.
In hindsight I wish we'd gone back to Trinidad for a a few more days instead of just Varadero - maybe next time!