The rainy season goes from May to end of October. You might have heard of 2017 hurricanes in September.
I recommend the dry season starting from November. It is also what Cubans call “winter”. This means about 30°C. I consider this very good for travelling, better than even warmer and rainy and thus humid.
The weather is typical tropical.
It was surprising to me to read that Cuba has a good health system, especially for Non- Cubans.
The “international” hospitals in Cuba have the corresponding level.
I was told beforehand that for immigration you need to show in Spanish language(!) a health insurance for abroad covering Cuba. When I went, no one asked me to show that.
People advised me more than once to not buy cigars from vendors on the street but when it came to crimes like robbery etc, I was told that Cuba is safe.
The district Havana Center at night might look intimidating like a slum, still it is safe.
Nevertheless be careful, especially women travelling alone.1
1 Dear Ladies, Cuban men are quite flirty. Be mentally prepared that they will try to talk to you.
It is easy to get from one place to the other. Especially to the touristy places. But even off the beaten track you will always find a "taxi driver", official or not. Or you use the local pubic
Most popular for tourists is the bus service "Viazul".
Usually I am not a huge fan of driving myself but in Cuba the traffic seemed to be less aggressive than in other countries (incl Germany ;-).
I prefer Viazul over mini- bus. Viazul seemed to be more reliable, better organised.
bus, taxi, (rental car)
A good cigar or bottle of rum is about ten USD. That does not sound cheap to you?
True and I guess the all- inclusive hotels are not cheap either.
But I think the rest of it is rather cheap.
My budget for 2 weeks incl flight: 1.400 EUR, also including rum and cigars. :-)
It is hard to find wifi in Cuba or let's say internet in general.
First of all you need to buy a wifi card in the post office (or shop). It is about 1-3 USD for an hour of internet. Second, you need to find a place with wifi connection.
It might be a bigger hotel (lobby only) or some bar or a public square. Best ask the locals.
Of course, this makes spontaneous booking harder. AirBnB doesn't work in Cuba at all for tourists. (Don't ask me how the locals do it, they do.)
If you go two days in advance to the bus station, you will get a ticket. Otherwise you will find a taxi driver, also for cross- country transport.
There is a lot of private accommodation for tourists ("casa particular"). These places are great: clean, spacious, local, all you need. They have a sign outside, so you will find them by walking around.
I have already mentioned cigars and rum, right? ;-)
There are great beaches. And there is other beautiful nature like Vinales.
So, plenty to do in Cuba.
For two week I would recommend to focus on one side of the island, east or west.
Your tour on the west side should include:
Havanna - Varadero (or another beach place) - Vinales.
Moreover Cienfuegos is popular. There is also Bahia de Cochinos with it's nice beach of Playa Larga.
And there is the island Cayo Largo in the south west.
In central Cuba there is Trinidad and "Che Guevara's city" of Santa Clara.
If you decide to go to the Eastern part, your equivalent to Havanna as a hub will be Santiago de Cuba. The beaches of Cayo Coco are superb.