I have kited Cuba 5 times all in november-december. Winds are typically 15-35kmph at that time of year (check wind guru for where you are going) we always take two kites so we never get skunked (14m/10m 12m/8m for a 200lb guy)
I find that i ride my bigger kite 80% of the time and could probably hold onto my bigger kite in the few days that it does blow enough to use the 8m. We typically go in groups of 20-30 people (ya lots of fun) to either varedaro or Cayo Guillermo. I can kite at about 22kmph and the past few trips have kited 11 out of 14 days and 10 out of 14 days.
IF you go to Varadero try to stay at Iberostar (really close to town, tis is one of two kiting spots) or even better yet at the very end of the penisula at barchello marina palace, you have a higher chance of riding in different direction around the point. varadero is becomming a tourist town, rent mopeds go hang out at Cafe 62 (or something like that) listen to the local music at the bars at night. A bunch of outdoor markets all with the same junk… the water conditions in varedaro are choppy (4-6’ floor depth) but if you rid around you can find some good flatspots when tide goes down, no real waves to speak of until you go farther out… and even at that they are mushy and not that great… be careful at Marina palace and if the wind is NW you can get blown past the penisula out to sea!
Cayo Guilermo is secluded… 2 hours from nearest village so dont expect to do any site seeing, just go there to kite, and the kiting is awesome. Cojimar hotel is becomming busier for kiting, it might be becase out the literally 1-3’ shallow water for about a mile out, ya its that awesome. down side… there is about 10’ of beach, rigging and launching kind of sucks and ALOT of people do water launches.
About a 20 minute walk down the beach is SOL. due to the hurricane last year the beach changed here, where it used to be super shallow it is now 4-6’ for half a mile out, a little more choppier then Cojimar but has a large beach for rigging
Cuban food is generally bland, salt is usually the only spice. Marina palace had the best food yet (it did cost a bit more). I am always full at the end of meals but never eat the healthiest. Check out travelocity and similar site for deals, if you are willing to go from a wed-wed it is usuaully cheaper then a sat-sat, play with the times. When we go 2 weeks incl tax is around $1400 and one week is about $900 (sometimes we find less).
All the best