Any person about to start a journey should try to have people escort him1.

Anyone who is escorted by his friends or others will not encounter any harm. Those who are leaving and who neglect to arrange an escort, or those able to escort who do not, are considered as if they have shed blood2.

A beis din has the authority to compel people to escort a traveler3.

Escorting a person comes under the category of gemilus chassadim4 , and also fulfills the mitzvah of “ve’ahavta lerei’achah kamochah” — “loving your fellow as yourself.” (Vayikra 19:18)5.

2. Accompanying a person without knowing that the latter is going on a journey is not considered escorting. The one escorting must know that the other person is going on a trip and intend to escort him in order to fulfill the obligation of escorting6.

3. A host is required to escort his guest who is leaving the city to continue his journey or to return home7.

[We see a fitting example from Avraham when he escorted the angels that had come to visit him (Bereishis 18:16) and when he established — “planted” — in Be’er Sheva an “eishel” (Bereishis 21:33) which our Sages tell us stands for “achilah” — eating, “shetiyah” — drinking, and “levayah” — escorting.]

4. The mitzvah of escorting only applies when the traveler is actually on his way out of the city8.

5. Even if there are other people who are escorting the traveler, it is still a mitzvah to participate9.

6. When one has a choice of escorting a group of travelers who are traveling in one direction or an individual who is traveling in a different direction at the same time, he should accompany the one traveling alone10.

7. The minimum distance that one escorts a person is 4 amos11.

8. When the traveler is leaving by car, one should walk alongside the car for at least 4 amos.

While it would be ideal to escort a traveler all the way to the bus or train station when he is so traveling, an escort of 4 amos is sufficient.

In the same manner, when one is leaving by airplane, he should ideally be escorted as far as the outskirts of the city [or even further until the airport], but 4 amos is sufficient12.

9. Those escorting the traveler should remain at the point of leave-taking until the traveler is out of eyesight13.

10. The traveler should not directly tell the one accompanying him to turn back and not continue 14, but he can allude in an indirect way that there is no need to continue escorting him15.

11. If one can not arrange for an escort, then he should occupy himself with Torah study16.

12. One should not take leave of a person traveling with tears and17, but rather with a joyous spirit18.

If one is unable to control his emotions, then the crying should be done in advance of the actual leave-taking19.

13. One should take leave of his friend with a statement of halachah. Then each time this particular matter comes up, he will be reminded of his friend who taught it to him20.

Preferably, the individual who is leaving should be the one stating the halachah. However, it is also acceptable if the one escorting says it21.

14. When taking leave of his friend and extending blessings to him, he should not use the phrase “Leich beshalom” (“Go in peace”), but he should rather say “Leich leshalom” (“Go towards peace”)22.

[We find that David used the phrase “Leich beshalom” to his son Avshalom (Shmuel II 15:9), and Avshalom ultimately met a tragic end by being hanged. On the other hand, Yisro used the term “Leich leshalom” when speaking to Moshe (Shemos 4:18), and he was successful.]23

The Maharsha24  explains that during a person’s lifetime his goal is to be successful in all his endeavors and in any place where he may be found. After death and burial, however, he has no chances to be successful or unsuccessful. Therefore, we say “Leich leshalom” to a friend going on a trip, meaning “May your endeavors be successful in your place of destination, and may you find peace there.” In contrast, the phrase “Leich beshalom” means that the peace should be in the going itself, not in the destination. Thus, we say “Leich beshalom” to a deceased person before burial, meaning that his burial should be peaceful and that he should encounter no obstacles in joining his ancestors [in Gan Eden].