Gibraltar (I know it's not Spain!)

oops never mind flying from there to madrid, nightmare and expensive.

I can direct you to Gibraltar from wherever you want by whatever public transport.
The closest you mention you may be is Ronda, an hour and a half or more on the train to Algeciras or San Roque (scenic journey) another half hour on the bus to La Linea and walk across the border. Or an a hour and a half by rental car, leaving the car in La Linea and walking across.

www.renfe com - trains
http://siu.ctmcg.es/en/horarios_lineas_tabla.php?linea=4 - the bus journey

We did it as a day trip (tour bus) from Albufeira in Portugal one year. Long day but worth it.

I visited by car as part of an Andalucia vacation. I parked outside the border in La Linea and took the bus across the runway.
Seville is, in my opinion, the prettiest city in Spain, therefore, if you have never seen it, you should go. While you are there, if you have time to spare, rent a car for a few days and visit the various pueblos blancos, like Ronda, Arcos, etc. During that driving trip, find time for a full day in Gibraltar.
To return to Madrid from Seville, you can take the AVE train. There are also low cost flights to Madrid from both Seville and Malaga.

Yes I should have mentioned- we will be there during semana Santa- so I am a bit scared off of Seville for that reason... Just me and my 13yo son. Though maybe I should reconsider that? Really wanted to go to Ronda though... We only have 4 nights though before we have to be in Madrid....

Kim,
I'd suggest looking at the South Ole Spain Tours web site, and then also email Emily (who owns the company) to inquire about a private journey for you and your son.....and then also compare the price for any group tours to Gibraltar her company might offer from a convenient location. She can even arrange your overnight stays, if you need help w/ that.

Check out reviews for her company on Trip Advisor.....that's how we found her.

My husband and I were in Spain this past spring, and we arranged transportation thru Emily, and it also included a stop in Gilbraltar (my husband really wanted to see Gilbraltar). Emily arranged the most wonderful private guide, and we were able to see everything we wanted to see efficiently and in a very well-informed way: cable car to the top, siege tunnels, the cave, the apes, the lighthouse at the point, and bit of the city......our guide made the few hours extra special. We actually traveled from Granada that day, with a stop in Ronda for lunch and some sightseeing, then Gibraltar, then on to our overnight in the old town section of Marbella. It was a long day, but a fun day, too.

And, I should add, that I was not super excited about going to Gibraltar....I did it for my husband, who was excited like you son. I actually wound up enjoying it and finding it interesting.......the excellent guide helped, I'm sure.

And, having the South Ole Spain Tours driver hand us off to the guide at the border made for a much more efficient crossing....we didn't need to worry about parking or finding our way (they both had cell phones). Traffic can be a zoo entering Gibraltar and/or departing, depending on time of day. Our crossing was seamless and quick.

My husband and I just returned from a two week trip to Spain and we did stop in Gibraltar. We were driving from Tarifa and planned to stop for maybe 3 hours and then head on to Granada where we were returning the car and eventually flying to Barcelona. Basically we just wanted to see the rock. We were quite surprised at the crowds. A cruise ship was in so I think the crowds were even larger than usual. Consequently, it took us 5 hours to get to the top of the rock. First, you have to go through customs which wasn't too bad. Next, you had to take a bus to a plaza and then walk to the entry gate where you purchase your tickets and que up for the cable ride to the top. We waited in line over an hour for the cable car. Once at the top you were greeted by monkeys. Very aggressive monkeys! Now, I do think a twelve year old would like the cable car ride and the monkeys. I thought the monkeys were gross and beware there are droppings everywhere. Yes, the view is spectacular from the top but there are so many other places to see in Spain. If you do go, check the cruise schedule to see when they are in port. Perhaps you could avoid that day. We were there on 9/28.

My husband and I just returned from a two week trip to Spain and we did stop in Gibraltar. We were driving from Tarifa and planned to stop for maybe 3 hours and then head on to Granada where we were returning the car and eventually flying to Barcelona. Basically we just wanted to see the rock. We were quite surprised at the crowds. A cruise ship was in so I think the crowds were even larger than usual. Consequently, it took us 5 hours to get to the top of the rock. First, you have to go through customs which wasn't too bad. Next, you had to take a bus to a plaza and then walk to the entry gate where you purchase your tickets and que up for the cable ride to the top. We waited in line over an hour for the cable car. Once at the top you were greeted by monkeys. Very aggressive monkeys! Now, I do think a twelve year old would like the cable car ride and the monkeys. I thought the monkeys were gross and beware there are droppings everywhere. Yes, the view is spectacular from the top but there are so many other places to see in Spain. If you do go, check the cruise schedule to see when they are in port. Perhaps you could avoid that day. We were there on 9/28.