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January and February in Europe can be the coldest most miserable months of the year...March and April it usually rains. Not sure why you're choosing this time of year? September and October are more likely to still be warm but mild - at least in the more Southern countries.
Since you're coming from the States (correct me if I'm wrong), prices here will generally be expensive. Portugal is more expensive than Spain in a few things, but then not in others. My favourite part of Spain is the North - amazing scenery and beaches, and still relatively unspoilt. Italy and Greece I am not very familiar with but I imagine they are nice holiday places all year round, Tuscany particularly. I would suggest Prague as a good Autumn destination too, it's a beautiful city. There are so many places you could choose from, Amsterdam, Brussels and Bruges in Belgium, in France I'd suggest staying in the Loire Valley, Dubrovnik in Croatia, the Southwest of England, like Cornwall...
In Portugal, for an autumn break I would suggest the north of Portugal, particularly the wine region of Douro. It's quite beautiful there, there's a lot of places to go exploring in the countryside, and it's good for a quiet break. The food is also good here, so that's another plus. If you're looking for beaches, I'd say Sintra and Cascais area are the best, or then the Costa Vicentina, which is basically on the lower west coast of portugal - lots of beautiful, uncrowded places there.
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Whether we write or speak or do but look
We are ever unapparent. What we are
Cannot be transfused into word or book.
Our soul from us is infinitely far.
However much we give our thoughts the will
To be our soul and gesture it abroad,
Our hearts are incommunicable still.
In what we show ourselves we are ignored.
The abyss from soul to soul cannot be bridged
By any skill of thought or trick of seeming.
Unto our very selves we are abridged
When we would utter to our thought our being.
We are our dreams of ourselves, souls by gleams,
And each to each other dreams of others' dreams.
Fernando Pessoa, 1918
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