I have been to Santorini, Corfu, Rhodes and Skiathos. Corfu was my least favourite, Lindos in Rhodes I fell in love with and hope to go back soon. Only thing is it depends on when you are thinking of going, I went in May at the beginning of the season, the first week was quiet so you could really enjoy the town, the 2nd week was packed with people but still a great vibe. The streets are very narrow and no cars are allowed.
If you don't like walking up hills I wouldn't recommend it, it certainly toned up my thighs! It has a couple of small clubs and a good choice of bars and restaurants, I'd say you get a good mix of all ages there, but probably no where near enough nightlife to attract the hard core clubbers, thank god!
Santorini was also lovely, again I went at the beginning of the season - to Perissa, and it was a bit too quiet, but it really depends on what you are after. Note Santorini has black volcanic sand and it's rocky under the water so not great for a paddle.
Skiathos island is small, I stayed in the town and had the best time. More traditional up the hill and cheaper, the bars and clubs along the front are pricey, but it does have a great atmosphere, and a plane landing you won't forget in a a hurry!
Imagine a British flag on a message board. Imagine it saying "English Breakfast" and featuring a picture of some greasy sausages and stale looking ham and eggs. Now, multiply it, so that it appears on every other door way, in every other restaurant in the centre of town... "Proper Sunday Lunch", "British pub food", "British Bar", "Sky sports". I had a beer - Una Cerveza por favor...? the guy says "Whut??? ENGLISH mate, speak ENGLISH..". If you like beer bellies and tattoos, and people getting drunk all over the place, go to the Canaries....
I was in Fuerteventura, and there's nothing interesting or exotic about anything - except maybe the beaches. And the volcanic black sand beaches. There's no spanish food, tapas, or anything remotely like it. The sea is beautiful but f-r-r-r-r-eeeeezing, even in summer....!!! We got so bored or the puppet shows and magic shows, and "pick a card" and "rock the boat", one day, we drove until we found something. It was a totally German town, with German beer, and wursts... so.. spend one exotic day eating sourkraut.
So, if you want to know how your granny went on hols - go to the canaries.
My husband and I have been to Cuba at least 30 times (stopped counting) We have friends in Cuba and have stayed in their home, visited their "stores" etc. Monetary tips are great, gifts are better. They can't get this stuff for any price. Take anything you can spare. Dollar store items such as bicycle repair kits, shoe shine kits, shoe laces, small tools, anitbiotic creams, diaper rash cream, baby medicine, tylenol, ladies sanitary products, scissors, safety pins,toiletries...(you get the idea) are invaluable. It sounds ridiculous, but they literally cannot buy this stuff (American embargo). Take your used (or new) clothing (summer), and shoes. The need for everything is desparate. Be careful when entering Cuba, as the officials will try to tax tourists for bringing gifts so don't be too obvious. If travelling with kids, leave behind that old stroller you don't need anymore, they're like gold. There is no insult taken if the gifts are given with dignity, and not given as pity to beggars. This is a great site for info, and I was glad to come across it.