I went to Cuba with JY a few years ago and it was by far the most rewarding trip I've ever been on. I went in Feb and the weather was perfect. Read up before you go on the Revolution and Che Guevara, will make it more interesting, unfortunately I didn't.
There were a couple of lovely 4* hotels but the rest were pretty basic, but everywhere the beds were comfortable and the bathrooms were OK (i.e. everything worked). There is a place at the Sevilla Hotel in Havana to change money and everywhere is the same exchange rate. The food was also basic and lukewarm, that's the way it's served in Cuba. Every hotel was buffet style except for one night to a local restaurant in Havana. Try and get to Hemingway's house outside Havana.
Take cheap pens, pencils, toiletries (esp small soaps) to dish out to schoolkids / women begging at coach stops. Soap seems very precious to them and we all have loads of toiletries at home from our holidays! I didn't bring anything and regretted it and you don't get a lot of toiletries in the hotels there.
We had a great local tour guide called Felix whom we met at Holguin, if you should be so lucky to have him please tell him I said "Hi". Leigh, the Tour Manager, was also excellent - unfortunately she only does an occasional trip for Travelsphere now.
Soak up the atmosphere at each place visited, explore Havana at night when all the old buildings are lit up & go to the Casa de la Trovas (bars with live music and dancing). Every town has a Casa and in Trinidad there's an open air one (bring repellant). Some hotels are a little out of the towns but share a cab (or a horse & buggy) with your companions and go into the towns in the evenings. People are friendly and love conversing with tourists and showing off their dancing skills. We had a salsa lesson in Santiago but it would be prudent to have a few lessons before leaving home (if you like dancing).
I hope to return to Cuba in 2013 and will probably do the same tour with JY again if it is still in their brochure.
