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Spain and Portugal in February

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I've decided to plan a trip to Spain and Portugal in February of 2016. I'm just in the first stages of planning, and trying to figure out exactly where to go and how to get there. Right now I'm thinking start in Barcelona, going to Sitges to check out Carnival, go to Madrid, maybe some other places from there, then Lisbon. We're thinking at least 2 weeks. My main questions are:

-Are there certain places we should definitely avoid because it's February? From what I've read it sounds like maybe we should avoid some of the towns in the north that can get cold and icy? We're from Oregon, so we're used to very rainy winters. The weather in Madrid actually sounds pretty similar to what we are used to, but with perhaps a little less rain.

-Transportation: I don't want to rent a car. I was looking at Eurail passes. I thought we would just take that everywhere, but then I saw how cheap it was to fly to Lisbon from Madrid, so we will probably take a plane for that hop. Are we going to miss out on things if we don't rent a car? Any thoughts on Eurail would be helpful.

Any other suggestions for places to go and things to see would be much appreciated. It's a little overwhelming at the moment. Here's a little background on us and what we're looking for: I'm 30 and he's 34. I've never been to Spain, but have been to other parts of Europe. My boyfriend has never been to Europe. In fact, he's never left North America! So he's definitely looking to see some history and culture. The oldest buildings he has ever seen were in Boston. I'm really looking forward to the food, as I used to work in the food industry. We like to eat and go to bars. I'm a big fan of cured meats, cheese, and wine, so any food related suggestions would be awesome. I'm also a landscape designer, so I would be interested in hearing about any gardens, though I know it's not going to be a good time of year to go. I'm fascinated by cork oak savannahs. We are both art fans, however I would say we both are more interested in modern and contemporary art. I would probably appreciate breaking up our time in big cities with some quieter areas. I get tired of constantly going from one historic site to the next, and the crowds, so I need to take relaxing breaks to keep from getting travel fatigue. Our last trip was to Kauai last fall, so we're not really looking for beach time or stunning landscapes.

It looks like there is so much to see, I'm sure we will find plenty to do in any city we go to. But any suggestions would be helpful.

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