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Portugal in October by car

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DH and I are just beginning to plan our trip to Portugal for October 2015. We are planning to rent a car and drive a circuit route including the coast/interior mountains. We have not determined where to fly into from US yet, and may end up flying in to Spain, fares will determine. We have 21 to 24 days, prefer off the main track, stay in rural communities, scenery, ruins, vineyards/wineries, kayaking, light hiking, pubs, good food, market shopping. Any suggestions as to routes to stick to; off main track things to see/do; any festivals or celebrations in October; hotel recommendations, hikes, kayak tours or other suggestions would be gratefully appreciated.
Also, does anyone know if there is an accommodation guide book I can order? Any tips on car rentals? (We are aware of the highway tolls)

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