The main plaza or Plaza Mayor is just a few steps from Puerta del Sol in Madrid. Your best bet is to take the Metro and get off in Sol. To make things even more right, be sure to cross the street from Sol towards the Ayuntamiento or City Hall and stand firmly with your feet on that marker that says “Kilometro O”. A very touristy behavior, but who cares?
To the right of the Ayuntamiento are 2 streets both ending in the Palacio Real and Almudena Cathedral area. The street on the right is Calle del Arenal where you would be tempted to drop by for churros con chocolate at Chocolateria San Gines. So take the road on the left instead. That’s Calle Mayor where you walk past Museo de Jamon ….. Oops.
On your left side, watch out for an alley that leads to Plaza Mayor. I think this is Calle Felipe III. Take this alley and be sure to drop in on this small shop where you can check out your “apellido” and buy a keychain with your family heraldry or insignia or emblem….. I found mine, and my family name like many Filipinos has Spanish roots. Mine is a special clan of mercenary warriors noted for their bravery. Paid soldiers!
Within the square you may want to visit the Tourist Information Center. You can pick up maps here and check out some guided tours. Many chose to do the “hop on, hop off” red tour bus for €20. If you’re not keen on walking and would just want to sightsee from your bus seat (it’s open on the 2nd level), then this is for you. Otherwise, take the unlimited tourist pass for €9.30 (1day) or €13 (3 days) which you can use taking the metro or bus and explore on your own. After all, the metro stops for the tourist sites are clearly marked and Madrid has a superb metro system.
Again, you’d find many street artists — should I call them plaza artists? OR buskers? — around the statues of King Philip III and the corners of the square. Many dining outlets too — mainly catering to the tourist crowd, I guess, judging by their patrons. You can have your paella and jamon fix in any of the tascas here. (Tascas mean “local gathering place”) Or you may simply have that sangria or cafe con leche with some tapas (appetizers) in any of the open-air bars and just people-watch. Buen provecho!
lifeisacelebration 
Very practical blog and makes me feel as if I am also there. We seem to have passed that way the last time. Nice Idea on the family name, would have to do that if there is a next time for me in Madrid. Continue to have fun exploring!
How’s the “light finger” situation nowadays? Marami pa ba?
Policia all around most tourist sites. If that’s any comfort 😉 Frankly, I feel safe but just the same, take caution.