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Help with Itinerary for Spain Portugal Trip

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I am trying to plan a 2 week trip to Spain and Portugal for the beginning of August. Neither my husband nor I have ever been. On our vacations we love to explore interesting towns and villages, soak up the culture and enjoy good food and wine. Last year we did Rome, Tuscany, Florence and Venice and loved the mix of city and small towns. We loved most of all driving around Tuscany and seeing all of the hillside villages and sittng at the cafes. The proposed itinerary for this trip is as follows:

Fly into Barcelona and spend 2 nights
Drive to San Sebastian and spend 4 nights with daytrips to Bibao, Santander (and welcome any other suggestions)
Overnight train from San Sebastian to Lisbon (arrive 10:00 am)
2 nights Lisbon (daytrip to Sintra)
Rent a car and drive to Algarve
3 nights Algarve
Drive back to Lisbon for our last night
Depart Lisbon back to US

Thanks to all for your feedback/suggestions

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