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Itinerary Help - 5 weeks Spain and Portugal Cities

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My husband and I are spending five weeks in Spain and Portugal in Oct/Nov to celebrate my 50th birthday. One week will be spent catching up with my brother and his young children who we will meet in Malaga. This week is not able to be changed. The rest I can change if it does not make sense. My flights are not yet booked so I can fly into or out of either Barcelona or Madrid.

We enjoy architecture, street photography, street food and understated restaurants and sculpture and street art over the classics. We like visiting cities and list New York, San Fransisco, Paris and Budapest among our favourites so far. Of smaller places we loved Verona and the lakes area of Italy over say, Florence.

We travel by public transport and stay in the family run rather than chain hotels. Bearing these things in mind, I have come up with this itinerary after looking through four guidebooks and numerous blogs and would love some critiques on it.

Flying into Barcelona from Australia – not booked so can change this
Malaga 7 days - to meet up with my brother for a family holiday (4 adults two small kids. Do very little other than catch up with each other and enjoy the sunshine + 1 day trip to Ronda (and perhaps Cordoba if we need a break from doing nothing lol) – can not change but at least it’s a beautiful house ;-)

Monday Barcelona – Jet lag day
Tuesday Barcelona
Wednesday Barcelona
Thu Barcelona
Fri Barcelona
Sat Barcelona /Malaga – Travel day – Train
Sun Malaga
Mon Malaga – Day trip to Ronda
Tue Malaga
Wed Malaga
Thu Malaga - Day trip to Cordoba
Fri Malaga
Sat Seville
Sun Seville
Mon Seville
Tue Seville/Lisbon – Travel day – Bus and Train or ?
Wed Lisbon
Thu Lisbon - Sintra day trip
Fri Lisbon
Sat Lisbon – Obidos day trip
Sun Lisbon
Mon Lisbon / Porto- Travel day – Train
Tue Porto
Wed Porto
Thu Porto – Travel day to San Seb – not sure best way yet
Fri San Sebastian
Sat San Sebastian – Birthday dinner
Sun San Sebastian
Mon San Sebastian / Madrid – Travel day – Train
Tue Madrid
Wed Madrid
Thu Madrid
Fri Madrid – depart mid afternoon for airport - flight to Australia

Maybe I should leave out Porto or San Sebastian as this seems like lots of moving although my husband is quite keen on Porto and I wanted to have my birthday meal in San Sebastian.

I had planned to do the trip in reverse going to San Sebastian right after Barcelona however, my brothers part of the trip is already locked in, and now I am a bit thrown.
Would appreciate any advice – our usual travel style is five days per place so this is slightly more moving than we are used to.

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