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Early Itinerary for Spain - 2+ Weeks

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Hi there, Fodorites!
I've been away from the boards for a bit basically dreaming of my return to Europe with emphasis on Spain. Such a beautiful country and I've only had the chance to see Valencia and Barcelona. I would be looking to go at a time most convenient for my work to allow me to be on vacation. The cheapest way so far I've found to get to Europe from Boston at this time of the year is to take advantage of Wow Airlines. Looking at it, a round trip from Boston to Paris is $360 US and then additional flights via Ryan Air would be around $70. Not too bad and this may be the best bet because I will get a night in Paris to visit a museum or just get a nice dinner before I return home.
On to the important pieces...SPAIN! Ah it makes me so excited just typing this loose framework of a plan.
Arrive in Madrid before noon February 16
Madrid + Toledo Day Trip Feb 16- Feb 19
Toledo > Cordoba Feb 20 - Feb 21
Cordoba > Sevilla Feb 22 - Feb 24
Jerez & Sanlucar (Vineyard traveling) Feb 25 - Feb 27
Ronda Feb 28 - Feb 29
Granada March 1 - 2
Granada back to Paris March 3
Fly Home to Boston March 4

Note, I am a 25 year old who loves a mixed approach to travel. I love doing a ton of walking, hiking, museums, exploring, eating, drinking, photography. I do not mind a quick approach as long as I get to see some major sites in each place. Madrid I will certainly be seeing at least 2 of the big 3 museums. I will definitely plan a trip to the Alhambra ahead of time. I am a sommelier who will have some connections in the Sherry Triangle so I should be able to either get accomodation or at least tours.
Does this look rushed? I know that is super hard to evaluate since I see so many diversely paced trips and we all have different ideas of needs and interests. I think there are plenty of opportunities to just take it easy as most of these destinations have places to just chill and breathe everything in.
Also anywhere on the list you might add time to or perhaps take out? Anywhere you might think might be of interest to me. Note, I'm a big history buff, love food, wine, architecture but also meeting people.

Sorry if I'm a little all over the place but if you need some clarification, please let me know and I will do my best.
Thanks as always People of Fodors

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