Road trip from Madrid and back to Madrid

You should look into train travel. Most of those places can be reached by trains including the fast trains.

Since you’re making a loop, the train wouldn’t be best because you’d need to keep going back through Madrid. Stick with getting a rental car.

Chinchón and Cuenca are east of Madrid while the other places are west of it. If you need to drop a couple places those are the logical places to drop. Cuenca deserves an overnight. Chinchón can be seen in a couple hours since the plaza is main draw. A couple years ago we saw the plaza and literally walked around the town in a two hours.

If picking up the vehicle at the airport and starting the loop from it a logical order is Segovia, Salamanca, Ávila, then Toledo, or the reverse. If you decided not to drop any place, then from Toledo head over to Cuenca and visit Chinchón on the way back to Madrid.

Ávila can be seen in a couple hours and you need to go past it when going from Salamanca to Toledo. From the airport, both Toledo and Segovia are about a 1.5 hours drive. I suggested going to Segovia first because it would get you away from the Madrid traffic quickest.

Regarding your “need to visit” comment, only visit places you want to visit because you have an interest in them. Don’t visit a location just because somebody says you should. There are some places that are frequently recommended to visit that I disliked. Hence, visit where you want. Do a little research to see if you might like a location and if it would be worth using your limited vacation time to visit.

You are super. Thank you very much

Salamanca is great but near the Portuguese border, some distance from Madrid.

Also, you can do Avila and Segovia in one day on a day trip from Madrid.

Totally agree with Jaime--pick the ones that call to you.
We took a car to Cuenca, stopping at Segóbriga (if you have an archaeology interest, good stop). We wanted the car for nearby hiking. With more time, we would have also explored Albarracín--once you start looking within an area, you'll find tons worth stopping for and may decide to cover less ground. Should have stopped at Toledo and Consuegra, too, but we could not help ourselves and drove over to the west of Madrid too. While I loved Extremadura, an ideal trip probably would have been east or west, and we had twice the time you had.

Segovia to Salamanca is a 2 hours drive. Salamanca to Ávila is just over an hour, and Ávila to Toledo is under 2 hours.

If going directly from the airport in Madrid to Salamanca it’s just under 3 hours.

If you didn’t skip Cuenca, it’s about 45 minutes from Toledo to Consuegra. Consuegra is worth visiting, but out of the way if headed to Cuenca or Chinchón. Toledo directly to Cuenca is about a 2 hours drive.

Thank you guys for your replies.

Truly, there is no NEED to visit anywhere.

I visit places and spend time and money there because I really, really want to see them.

Madrid is full of action and activity. You could spend all five days there easily, visiting the museums, the Royal Palace, and so forth. You can also take day trips from Madrid, so you could potentially stay in the same hotel the whole time, instead of checking in and out on a short road trip. The trains would work well with that decision.

Toledo is a minimum half day to whole day. It is a very lovely preserved medieval town with a gorgeous cathedral. The same time amount goes for Segovia (great castle), and Avila (stunning walls.).

IMO your city list is too long and too rushed, even with a rental car. You should do some research by reading travel descriptions and looking at photos to see what really interests you and your wife. Then plot out the driving distances and plan accordingly.

By the way, the Spanish performance art form is called flamenco. A flamingo is a pink bird. Knowing a little Spanish will make your getaway trip more successful.

Some flamenco shows offer dinner, some don't. You will need to check out the various options. Dancing is just for the performers. If you and your wife want to dance, you will need to go to a nightclub (very popular in Madrid!).

Feliz cumpleaños to your wife, and buen viaje!

Thank you.
I got a few advices so I think I already have the plan.