Instructively-speaking, I always make the sign of the cross when passing by a
known Catholic church, when I hear any sirens anywhere in the city, when passing by a cemetery of any sort, when eating (I try to do it before and after), and when I pass by a crucifix.
Obviously the sign is good near any Catholic church, given that our blessed Lord is really there, enthroned on high. Though I doubt peasants in the Middle Ages would bow when passing in front of the residence of the King, it seems a noble thought to translate into religion.
The sirens always alert us to some emergency. In an emergency, a person may be on the very brink of death. If it’s a fire engine, many people may be about to die, and those brave firefighters need as much strength as they can get. If it’s a vehicular accident, a heart attack, or any other thing requiring an ambulance, those skilled medics need as much strength as they can get! If it’s a police response to a bank robbery, assault, or even murder, those heroic police officers need as much strength as they can get to apprehend the unrighteous one(s), protect the victim, and serve justice. I believe strongly in offering the sign of the cross for them, and asking Jesus to help them: and St. Michael to defend all of them in the battle they go through. You don’t really
need to do this, but it makes me think I’m helping, in some way, against the demonic armies, whose master would just love it if someone died in a fire without having forgiven a brother or sister, or perished from a heart attack without having gotten to confession.
Naturally the cemetery must elicit a cross from us! At the very least, say “May the souls of all the faithful departed, through the mercy of God, rest in peace”, or just “May the souls of all the departed…”! You can’t just pray for the poor sinners who are alive… you need to help those who can’t help themselves! Whenever passing a cemetery and making this sign, I try to say “Thank you (at the head) Lord (at the heart) for the gift (at the left shoulder) of death (at the right shoulder), from which may proceed life, if we are diligent in faith, hope, and charity. Have mercy on these my brethren; may all the souls…”
There’s the famous story of a Dominican priest who only ever offered Mass for poor sinners on Earth. A brother came up and asked the priest why he never offered Mass for those in the purgative state. He asked the priest whether he would more readily give bread and alms to a poverty-stricken man in full health, or a poverty-stricken man who had lost all his limbs. The priest naturally said he’d help the crippled man first. The brother explained, then, that those in Purgatory can no longer help themselves, so they deserve our prayers first and foremost, and then those souls still in battle in the world. The priest immediately started offering Mass for poor souls…
The Dominican tradition gives an injunction (the 9 Ways of Prayer) to deeply incline the body when passing before a crucifix. As this is not always possible in some spots or situations, I at least try to make the sign. It reminds me of what Jesus Christ did for us, and makes the crucifix an active thing of contemplation, rather than a passing curiosity. Specifically, I say “Thank you (head) Lord (heart) for the gift (left) of life (right).”
Always make the cross over food and drink, because it is only by the Cross that we have full life, grace, and faith from “the Father of lights”. Remember the ray of light that shines on each human soul from Heaven, beatified and illuminated by Christ’s resurrection. I always imagine that He left a big hole in the fabric of space and time on His ascension, and the light of eternity pours into the world from it.

Whatever the case is, know that food gives you life… but the cross gives you greater life, so it’s natural to take food into you with the cross. Always thank God every second you eat, even if it’s just some water or a muffin. Muffins were made by God for us to enjoy and rejoice by eating their wonderful moist taste! Thank Him with the Sign!