Some of the great small cities of Spain are a short distance from Madrid and make for wonderful touring. Segovia, Avila, and Toledo are all nearby Madrid and offer wonderful vacation opportunities.
You can visit these cities on day trips, but to really soak up all they have to offer, consider renting a car and driving. This loop can take four to five days depending on how long you linger. Combine it with a visit to Madrid, and you have a splendid week or two-week vacation.
We don’t recommend driving in the city of Madrid itself, but getting a rental car in town and driving out on your tour – that’s pretty straightforward.
El Escorial Palace. The sprawling complex of the El Escorial Palace is worth a stop. This combination monastery and palace is about an hour drive from the capital. There are furnished rooms to visit, and a great library to see, but the highlight of this complex is seeing the final resting place of four centuries of Spanish Kings and Queens: the Royal Pantheon. You can make this a mid-day stop, see the palace, have lunch in town or at the Palace cafe, then continue on to Segovia.
Segovia. Segovia is fifty miles from Madrid. This town perches on a hill and represents a couple of eras of Spanish history with both a fairy tale castle and a Roman aqueduct. The town was started by the Romans. What is left of the aqueduct is 2,500 feet long and 100 feet high. Its double arches anchor one end of the town. Have a dinner of suckling pig (cochinillo asado) in a restaurant next to the arches of the aqueduct.
Stroll the narrow, mostly pedestrian streets to the other end of town to see the Alcazar castle. It looks like a fairy tale castle because it burned in 1862, and it was rebuilt in this exuberant style. There are historic furnishings inside and a great view of town from the tower.
Segovia is well worth spending a night. Just be aware, it can be crowded on weekends. Parking is scarce, so make sure to secure parking along with your hotel.
Avila. Avila is a city which could be overlooked, but if you’re into city walls, you shouldn’t miss it. The walls are intact, complete with 90 towers, and all this dates back to the 11th century. Avila was the birthplace of Saint Teresa and is an important pilgrimage site.
Once you’ve seen the museum and the Convento de Santa Teresa, head for the city walls. The lively section of town is just outside the main gates. Sit and have tapas and enjoy the view.
Toledo. The next stop on your tour of Spain is Toledo, which is about an hour south of Madrid. This former capital of Spain sits on a hill, surrounded by its city walls and the Tagus River. It has retained its medieval charm with city walls and winding streets – and lots of hills. It’s a fun city to wander and get lost in.
See the Cathedral and the Iglesia de Santo Tome where El Greco’s painting El Entierro del Conde de Orgaz is on view. Discover more of El Greco all over the little city. Wandering will uncover bits of Toledo’s Roman, Moorish and Jewish history as well.
To complete your tour, find a Parador to stay in for one more night before you return your car. Paradores are historic buildings that the government has converted to hotels.
Siguenza Paradore of El Cid fame is a castle turned into a hotel and is about an hour outside of Madrid. From here it’s easy to get back to the airport and catch your flight home.
More resources for touring Spain:

Lonely Planet Madrid (City Travel Guide)
Price: $14.95
Madrid plus day trips to Toledo, Avila, Segovia, Aranjuez, Chinchon, Alcala de Henares, Sierra de Guadarrama, Sierra Pobre, San Lorenzo de El Escorial and Valle de los Caidos. Features a perfect mix of the iconic sights and local bars, restaurants, galleries and shops. Our resident author helps travellers get to the heart of the place.

Madrid (Eyewitness Travel Guides)
Price: $13.6
DK Eyewitness Travel’s full-color guidebooks to hundreds of destinations around the world truly show you what others only tell you. They have become renowned for their visual excellence, which includes unparalleled photography, 3-D mapping, and specially commissioned cutaway illustrations. DK Eyewitness Travel Guides are the only guides that work equally well for inspiration, as a planning tool, a practical resource while traveling, and a keepsake following any trip. Each guide is packed with the up-to-date, reliable destination information every traveler needs, including extensive hotel and restaurant listings, themed itineraries, lush photography, and numerous maps.

Madrid Inside Out
Price: $9.31
This innovative little travel companion comprises 2 detailed, fold-out maps with a 64 page, full-color illustrated guide. The guide opens with 2 of our favourite itineraries. If you’re short of time and want to see all the best bits, these itineraries are sure to help you explore and savour the best that Madrid has to offer. The guide is then divided in to 7 chapters: see it – the best places to see from museums & galleries to markets, monuments and much more; buy it – pinpoints the key shopping areas and stores to target; watch it – places to be entertained: shows, theatres, music venues, ballet, comedy, cinema and nightlife; taste it – from ethnic cuisine to local fare to the top places for an evening cocktail – all the best places to eat and drink; know it – all the practical information you need to get the best out of your trip; directory – hotel listings, additional places to visit, annual events and useful websites; speak it – essential local words and phrases. In addition to the 2 detailed street maps there is also a transit map.