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Help me plan a 2 week trip to Spain and Portugal

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My wife and I are considering celebrating our special wedding anniversary in northern Spain and Portugal this March. A few years ago we were in Malaga, Granada, Ronda, Sevilla and Barcelona. This year we want to plan an itinerary that includes : Madrid, Bilbao, San Sebastian and Portugal ( possibly Porto, Sintra and Lisbon over a two week period. How would you plan this itinerary? How many days in each location? Transportation? When in March would it best to travel? Our travels will begin in NYC.

Thanks!

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