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Spain Itinerary advice please – Extremadura? Cadiz?

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<Hang in there; this is a long one as I have to address any possible questions in advance! If you like, you can skip down to “MY BURNING QUESTIONS”. Thank you!!>

We are very excited to be heading back to our favorite country (so far), Spain! We fell in love with Sevilla years ago – to the point that we are thinking of spending 6 months per year in our retirement there, so felt we better head back and see if we still think it still fits that particular bill. As we haven’t been to Madrid yet, we plan to go there and see Toledo and possibly Segovia as well… and now are trying to figure out where to spend our time before finishing our trip in Sevilla. Please help!

About us: We are in our early 40’s and would consider ourselves leisurely travelers: we like to “try on” local life in each place we go (in the back of our minds is always, “is this a place we could live?”) and are pretty relaxed in pace (a morning at sites most days is fine but the afternoons will be whiled away on a plaza, in a wine bar or pub. Of which we hope there are a number of options if we are overnighting – so not too small a town). That being said, we are not super into big cities – though appreciate it when we can find pockets that feel like our pace (we love the El Born neighborhood in Barcelona, for example, and the Santa Cruz barrio in Sevilla). I like museums, the hubs doesn’t. I can usually get him to “do” 2 per trip without complaint… but he may even skip the second one. Though he did love Fondation Maecht last year. Finally, we like being able to walk everywhere and try to take trains rather than drive, unless we would be missing some major beauty (e.g., we loved driving to Ronda years ago, as well as through the Pyrenees from Barcelona to Basque country. But never in the cities – besides the stress, we drive each other crazy with directions!).

Here is our current itinerary for 14 full days in Spain in early to mid October (this is as late as we could to go as we know it will still be sizzling – at least to us wimpy Seattleites – in Andalusia then). I include train travel time – taking the speed train whenever possible – in parenthesis.

Fly into Madrid (Day 0: we arrive in the evening); out of Sevilla (Day 15: we leave at 10:30am)

Day 1-3: Europe-based friends are meeting us there, so no flexibility on changing. I hope we hit the Prado and some other spots together and perhaps day trip to Segovia. I’m guessing Segovia one of those won’t happen, though.

Day 4: day trip to Segovia - assuming we don’t get there before then (0.5 hr)? Is this “worth” it given the balance of our itinerary? Spend the night in Madrid? Or head to Toledo now? (I’m not even sure if this is possible/manageable)

Day 5: morning speed train to Toledo (0.5 hr); overnight in Toledo (1 night in Toledo/1.5 days)

Day 6: Train (or rent a car; 5+ hours)? To Extremadura (Caceres, or…. My research into this part of the country is just starting so I’m not v familiar)? Overnight in Extremadura

Day 7: explore Extremadura; overnight in Extremadura

Day 8: train to Cadiz (4-5 hours)

Day 9: Explore Cadiz (do we need a car?)

Day 10: morning train to Sevilla

Days 11-14: enjoy Sevilla

Until Sevilla this feels like it might be a bit hectic for us between travel time and compressed time in Extremadura and Cadiz. As such, here are the questions that immediately come to mind that I hope you can help with:
• Is Segovia worth spending another 1-2 nights in Madrid? Or should we skip it this trip and move on to Toledo?
• Should we include Extremadura this trip or save for another time?
o If this trip, how many days is optimal, what towns and do we need a car for the best experience?
• Pretty much the same questions for Cadiz. I’ve seen trip reports that are split down the middle between raves and hates (though I don’t know the reasoning for those that didn’t like it). Part of me wonders if this could actually be an “it” (“we could live here!” place for us, perhaps combining the charm and history of Sevilla with the sea, in which case we should definitely make the time to visit this trip! (Being from the US northwest, we love the water.)
o Again, do we need a car? We don’t necessarily need the beach – certainly not the unrelaxed crowded kind we found in the French Riviera – but we do love a more laid-back beach restaurant/bar seen like we found near the Calanques de Cassis.

Thank you so much for your patience in reading this and your sage advice!

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