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Itinerary help: DF, SMdA, Guanajuato, Puebla, Oax

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Hola:

I'm traveling to Mexico 10/20-11/4 (approx 14 days-might be able to eek out another day) and trying to work out my itinerary. This is my first trip-very excited to visit this magnificent country! Using FF miles. Would like to be in Oaxaca for Day of Dead. My details: I like to wander/explore, see the must sees, and do one or several guided tours (walking and bus overview when I arrive). I like fabulous guides, charming B&Bs conducive to meeting other travelers and/or interesting historic hotels. Not beachy or sporty-so I prefer to focus on the people, history, culture, architecture, folk art. Solo female. Vegan diet. Sadly I don't speak Spanish, but understand a little b/c I speak some French. Budget is somewhat flexible since I'm using miles. I want to do it all, of course, but I think this trip I'd like to visit Mexico City, San Miguel de Allende, Guanajauto, and Oaxaca. Possibly Puebla if I take the bus from DF to Oaxaca.
--I think I'd like to spend 5-7 days in Oaxaca. 2-3 days in DF and 2-3 in SMdA. Maybe a day in Guanajuato and a day in Puebla en route to Oaxaca. The math might not work out...does this itinerary look doable or too rushed?
--Should I split it up in a different way - how much time should I allot for these places? Or should I drop one or two locations and save for another trip-if so which one(s)?
--Should I fly to Guanajuato first then head to San Miguel and then DF and on to Oaxaca? Or start in DF? Or DF after after Oaxaca before going home (hotel might not be available though). Since I'm using flyer miles, I have some flexibility and can consider flights vs bus.
--Would you fly to Oaxaca from Mexico City or take scenic route via bus, stopping overnight in Puebla?
--Will I be able to navigate subway travel with limited knowledge of Spanish language?
--I've done some searching and will continue to review, but wanted to ask for guidance now because the B&B I like in Mexico City has very few openings so I hope to make some decisions tonight about when to go to DF before it's sold out.

Muchas gracias.
PollyB

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