I always prefer the car for long hauls on land. However, as anybody living in Europe can tell you, the trains are in, as well as tramways, buses, metros etc etc, done them all over the years. One reason I can write/talk about it well. Of course, nothing beats the view driving into Toledo !! Let me tell you a bit on driving into Toledo !!!
Toledo is about 71 km (about 44 miles) from Madrid. From Toledo part the N-400, which connects this city with Cuenca by Ocaña and Tarancón. There is now an excellent A-40 autovía de la Meseta Sur,(old autovia de Castilla La Mancha) that unites Avila with Maqueda (where it links with the Extremadura highway), Toledo, Ocaña (where it joins the highway of Andalusia), Tarancón (where it connects with the highway of Levante, Valencia), Cuenca and Teruel. A former national road 401 Madrid-Toledo-Ciudad Real was transformed at the end of the decade of 1980 in the current A-42.
I have done the driving from Madrid , but the last time was from Cuenca on the A40 (autovía de la Meseta Sur) direction Toledo/Madrid before getting off on the N400 for Toledo. Thus, getting to Toledo from Madrid by car is easy and fast. To drive to Toledo, by road from the North, the main communication routes are the AP-41 (Madrid-Toledo Toll Highway) and the A-42 or Toledo Highway. From the South, the A-4 (Madrid-Cádiz highway), the CM-42 (Los Viñedos highway), or the N-401 from Ciudad Real. To get there by road from the West, its natural link is the A5 (Madrid-Badajoz motorway), currently connecting via the N-403, until the works on the A-40 are completed. Finally, the routes to the East or Levante are the A-3 (Madrid-Valencia motorway) and the N-400, as a link to Toledo.
The A40 route currently defined is the one that goes from the autovia A-5 in Maqueda to Cuenca, of which about 170 km are open to traffic, divided into two discontinuous sections. From Maqueda to the Northwest junction of Toledo, the hightway has been designed as a variant of the current N-403, except for the Torrijos ring road, whose route it takes advantage of. From the A-4 motorway to Tarancón, where it connects with the A- 3 (Madrid-Valencia) and from there to Cuenca, the highway has been designed as a variant of the current N-400, which has remained a service road for most of its length.
Now you have very good signage to get you into Toledo, but once you get there ,the idea is find a nice parking and walk the city! Some of the paying parkings I like over the years have been the Parking Miradero Calle Gerardo Lobo, S/N ,and Garaje Santo Tomé Calle Santa Ursula, 3. However, fine tuning over the years we took on and continue to use the Parking Corralillo San Miguel ,Paseo del Corralillo San Miguel s/n. You can get to it coming on the A42 go over the Tajo river and turn immediately left into Avenue de Castilla La Mancha (the Tajo river will be on your left), this same road becomes name Paseo de Cabestreros you will see a rocky hill wall on your right and bear right into Calle de la Candelaria and then immediately right into Paseo del Corralillo de San Miguel, and the parking entrance is straight ahead on your right hand side . To pedestrian exit you go up and be on the back of the Alcazar and Army museum! And right into the old town!
Now we have tried the free parkings but there are more inconvenient for walking into old town me think. They are the Parking Azarquiel . It is on the other side of the bridge of the same name, about a 12-minute walk from the center. Near the train station, a bit further away, is the Parking Saba.By popular demand, of the free parking the best is the Parking Safont. It is right in front of the bus station, so then you will have to get to the center which from the Toledo bus station get on Avenida Castilla La Mancha, about 10 minutes walk from Plaza Zocodover. You need to access the escalators, or Safont ski lift, to go up to the historic center of Toledo.
The General trafic Directorat see provincia and put Toledo, then click buscar : http://infocar.dgt.es/etraffic/
The Turriano road trafic and parkings in city of Toledo: http://www.turriano.org/
Best to browse the above two sites before coming and have a bearing on the traffic and parking. And of course, the tourist offices.
The Toledo tourist office on their locations: https://turismo.toledo.es/recursos/oficinas-de-turismo.html
The Castilla La Mancha region tourist office on Toledo: http://en.www.turismocastillalamancha.es/patrimonio/toledo/
There you go folks, another easy trip to a wonderful huge city to be a must to visit while in Spain. Toledo is indeed a require visit in Spain. Be happy with the road warrior and the above info, if in doubt ask me. Again, enjoy the post as I.
And remember, happy travels, good health, and many cheers to all !!!