If you’re looking for a day trip from Madrid, there’s the obvious of Segovia and Toledo. If you’ve done those before, I recommend driving up north to Manzanares el Real. It’s an easy 50 km drive from Madrid. Once you get out of the Madrid suburbs, it’s quite lovely. You will drive past green, sheep filled pastures and see the snow capped Sierra Guadarrama.
To arrive, I recommend taking the A6 to Collado Villalba. From their your GPS will take you through small roads to the town. Once your arrive you will find free public parking at the base of the New Castle, also known as the Castle of los Mendoza (because it housed the Mendoza Family). To arrive there directly, type this into your GPS or iPhone: Calle Cañanda, 28410 Manzanares el Real. You can also take a bus from the bus station (Intercambiador) at Plaza de Castilla.
Once you arrive into town, walk into the Plaza Mayor and have a caña (small beer) and tortilla at one of the outside terrazas. Next stop: you must visit the castle. Construction on the new castle started in 1475 on an old Romanesque-Mudéjar settlement. You can visit it for 5€, which I highly recommend. I’ve been to a number of castles in Spain, and I think this is one of the best preserved. There is a very interesting museum inside with beautiful tapestries and interesting artifacts. Plus it explains a little bit about the life in a castle back then. Finally, you can go to the top, walk around the ramparts and even climb up into the turrets. The view from the ramparts is beautiful: on one side is the reservoir Santillana and on the other, the snow capped peaks of the Sierra.
After a quick stroll around the town, get back in your car and drive to Guadarrama (it’s on the way back to the A6). There is a restaurant there called La Sala that is a Madrid institution. It is homey and yet elegant and famous for its grilled shrimp, which are excellent. It also has very good croquetas and homemade ice cream. If you plan on going for lunch, make sure you either get there late (around 16.00h), or make an advance reservation. This is especially true if you come during the weekend, or during a holiday as many families drive up here from Madrid for lunch. There is a large outdoor play area for kids and ample parking.
I recommend arriving for your reservation a little early and ordering a vermouth before lunch. Although they don’t have it on tap (del grifo), they have an excellent selection of bottled vermouths. The bar is large and dynamic with a comfortable, elegant lounge area. However ask the waiters before you sit in the lounge as there is often a waiting list.