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Help Wanted - Spain Itinerary

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My wife and I are planning our first trip to Spain this May. We've got approximately 23 days available with some flexibility. We intend to begin in Madrid and have teed up 5 days there, including day trips to Toledo and Segovia. We want to end our journey in Barcelona, where we've also planned 5 days including a day trip to Montserrat. Madrid and Barcelona are our most valued stops based on our love of big cities in general, but specifically, art, history, museums, architecture and semi-aimless wandering. We're also big cava fans and would love to tour a winery or two while in the Barcelona area.

It's the remaining time that's vexing us. We'd like to head south from Madrid before going to Barcelona but don't want to be too rushed and would like to rely on public transportation if possible. Here's our tentative itinerary.

Day 1 - Arrive in Madrid from London
Days 2 thru 6 - Explore Madrid, plus day trips
Day 7 - Train to Seville, afternoon for orientation
Day 7 and 8 - Sightseeing in Seville
Day 9 - Day trip to Arcos de la Frontera
Day 10 - Train to Cordoba
Day 11 - Cordoba
Day 12 - Train and bus to Ronda
Day 13 - Ronda
Day 14 - Ronda to Granada by train
Day 15 and 16- Granada
Day 17 - Grenada to Barcelona (fly?)
Day 18 -22 - Barcelona, plus day trips
Day 23 - Fly to London

So, the time after Madrid feels squished and frantic, but we're intrigued by what others have shared about these towns and cities. We're also wondering if it would be better to turn the whole trip on it's head and start in Barcelona, as it feels like the most isolated spot insofar as accessibility to the other locations is concerned. We're also interested in Valencia, but recognize it's not likely possible.

The only other thing is timing. We chose May because we don't want to be there when it's too hot, but would also love to do some beach time in Barcelona. We've visited Mediterranean seasides in France and Italy in May on other occasions and found the swimming cool but definitely do-able. Hoping Barcelona would be about the same.

Thanks in advance.

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