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We like Greece for food, history. Spain for more familiar (to us) language, design and some history. Going to Portugal next week, so I'm withholding judgment. What I have read in my studies, and, of course, tempered by the price of travel today, it looks like food/drink will be more affordable in Portugal than either of the others. I will post a review when we get back.
I love them all. They share some similarities, particularly for those not going to Europe frequently.
Given you live in Calgary, you must factor in airfare. Spain is more accessible with better fares. Greece is the most expensive. Also, in Costa del Sol area, you can drive to quite a number of towns along the coast.
TS is more abundant in Spain. Quality in my opinion is better.
I loved Rhodes Greece and Mallorca Spain for timeshare vacations. Both very different in "flavor" but both remarkably beautiful. I must say the people on Rhodes were among the friendliest I've encountered abroad. But Mallorca has magical natural beauty. Never have been to Portugal but would love to go. Have fun planning!