From Madrid, Toledo is about 70 km southwest on the A-42 freeway, which is marked "Toledo" on all road signs. This used to be labelled the N-401, and old maps or signs may still refer to that, although almost all road signage appears to have been updated. There is often spot congestion during peak hours, sometimes as far out as Parla (25 km).
Parking on the narrow cobbled streets of inner Toledo is virtually impossible except for short loading/unloading stops, but there's a big garage in Calle de Santa Úrsula, right in the centre.
Buses run between Toledo and Madrid's Plaza Elíptica bus station (on the grey Circular metro line) every half hour until 21:30. The company is Alsa (old Continental-Auto). The trip takes about one hour and a return ticket costs €9.12. From the Toledo bus terminal it is a steep but picturesque 20 minute walk up to the old town. A local bus service is also available. To catch a local bus from the Toledo bus station to the center of town, head out of the station for a bit and you will see a bus stand, catch a bus going to Plaza Zocodover. Among other buses you can also catch Line 5 from the same stop which runs every 15 minutes and will drop you off right in front of Plaza Zocodover.
The AVE high-speed train takes 33 minutes from Madrid's Atocha station to Toledo and costs €12.10 + €9.70 = €21.80 for a same day round trip, and you have to specify your return time at time of purchase. Be sure to arrive on time, at least 1 hour before scheduled departure time in Atocha. Boarding starts 30 minutes prior to departure and the gate will close 5 minutes before schedule. Procedures are less strict upon returning from Toledo however keeping a 30 minute margin here is recommended.
In Madrid they have installed many vending machines. However, be careful