I went in July, to both countries, and was miserably hot, but maybe May would be better. Can you select Barcelona? I LOVE that city -- visited it *twice* in the course of a six month trip! Lots of people seemed to like the beaches (and perhaps the waters) at San Sebastian, which is along the northern edge of Spain -- might be good snorkeling. I really didn't care for Italy much on the whole, b/c it was way too hot and humid, too crowded, too dirty, and all those famous historical sights just a bit underwhelming. If I went again, I'd probably spend more time touring the countryside and less in the big cities, though Florence is nice -- and Venice is just plain interesting.
Colleen... I've been saving your message till I could get a chance to have my Grandma answer it. She and my grandfather spent a month in Malaga about 3-1/2 years ago (in fact, it was just after they returned that he lost his sight, so it was their last real big trip). I wanted her to give you her insight in her own words, so the following is dictated by her and typed by me. Hope it helps! Denise ***********
Malaga is the main hub for the airport. We were there and stayed for a month, just East of Marbella. Yes, we did rent a car. It would be quite a drive to Portugal, really. However, the countryside is pretty. There are flights from Malaga to Portugal. I'd say to drive to Portugal would be a couple days' drive. I don't think you could do it in a day. We took bus tours from our resort, up into Rhonda. We also took a bus tour to Gibraltar, and took the ferry across to Tangiers, where a bus picked us up and took us on a tour into the country, and we had lunch in a Moroccan tent (which was delightful!). A trip well worth taking. The ferry itself is nothing to brag about, but you're not on the water for that long a time. We've been there twice. Both times, staying on the south coast. Thoroughly enjoyed it. The second time, we were there in May. Warm in the daytime, cool at nights. We found the people friendlier than most areas of Europe where we've been (note from Denise: and they've been EVERYWHERE). Have a wonderful trip!
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