Cuenca

Your itinerary looks much more sensible than most that appear on these forums (fora?). You've actually given yourself a bit of time to see some of the cities. I would skip the Cadiz trip as it's not worth the hassle for such a short visit. And give yourself lots more time in Granada (also remember to arrange your Alhambra ticket in advance).

One last thought: why aren't you going to Cuenca?

She is going to Cuenca on day 7.

Thank you for all your help. BTW cruisluv, I'm a man! lol

Okay, after much thought and many adjustments I have finally created this itinerary! Please tell me what you think. I am travelling to Spain mostly for a cultural experience (museums, castles, ect.)

Day 1. Arrive in Madrid
Day 2. Explore City
Day 3. Explore City
Day 4. Explore City
Day 5. Visit Toledo by train (stay in Madrid)
Day 6. Visit Cuenca by train (stay in Madrid)
Day 7. Visit Segovia by bus (stay in Madrid)
Day 8. Visit El Escorial by train (stay in Madrid)
Day 9. Visit Ávila (stay in Madrid)
Day 10. Train to Sevilla via AVE, explore Córdoba on the way (stay in Sevilla)
Day 11. Explore City
Day 12. Explore City
Day 13. Explore City
Day 14. Visit Cádiz by train (stay in Sevilla)
Day 15. Train to Granada, explore city, and then train to Valencia (sleep on train)
Day 16. Explore City (stay in Valencia)
Day 17. Train to Barcelona (stay in Barcelona)
Day 18. Explore City
Day 19. Explore City
Day 20. Visit Montserrat (stay in Barcelona)
Day 21. Train to Madrid via AVE (Explore Zaragoza and Calatayud on the way)
When in Madrid board flight home

ttt

I would also skip Cadiz, stay a day longer in Granada and found another day somewhere for Barcelona.

We just came back from Seville, Madrid and Barcelona. I can recommand the 3 hotels we stayed at each city, all at the best location of each city IMO.
Room Mate Alicia in Madrid - we were able to walk to all the museum and also Plaza Mayor and Palace within 15 mins. Nice staff and clean and comfortable rooms. We paid 140 euros for an excutive double room with balcony include breakfast. Also free internet.
Hotel Vincci La Rabida in Seville - beautiful hotel again right in the city center. Walk to Cathedral and Palace within 10 mins. We paid 188 Euro for a nice double room w/o breakfast but there are plenty of breakfast places around, no need to take the 15 euro breakfast from the hotel.
Hotel Inglaterra in Barcelona - again the best location you could ever ask for and the aerobus terminal is only 5 mins walk away. We paid 114 euro for a nice double room w/o breakfast. You could walk to department stores and tons of shops within mins and it was just great.

Thank you!