68:6 A person should donate to charity before departing on a journey as per Psalms 85:14, “Righteousness precedes Him and make His footsteps a road.” (The word “tzedek” – righteousness – is the root of “tzedaka” – charity.) One should also seek that the great leaders of the city should give him a blessing for success on his journey. It’s also good to have some people accompany him on his departure. When a person accompanies his friend, he should remain in the place where they part until the one going on the journey is out of sight. When blessing someone who is going on a journey, we do not say “Go in peace” but rather “Go to peace.” This is because King David bid his son Avshalom, “Go in peace” (2 Samuel 15:9) and Avshalom ended up being hanged. Yisro, on the other hand, bid Moshe “Go to peace” (Exodus 4:18) and Moshe went on to thrive and prosper. One should study Torah on a journey as per Deuteronomy 6:7, that we should speak of Torah “when you walk on the way.” One should also say recite some Psalms each day, with proper concentration and humility. A person should be sure to take bread with him even if he isn’t traveling all that far. One should also take an extra pair of tzitzis with him in case the first pair becomes unfit, which would prevent him from fulfilling the mitzvah. (Mishnah Brurah 110:20 advises bringing one’s tallis and tefillin even on a day trip, just in case one is delayed in returning.) The Talmud in Pesachim (2a) says that a person should always enter in “it was good” and depart in “it was good,” meaning that when one heads towards the place where he will spend the night, he should enter while the sun is still shining and depart the next morning after sunrise. This is advisable based on Genesis 1:4, “G-d saw the light and it was good.” A person should not eat too much when on a journey.
68:7 When staying over, one must check that things are reliably kosher. If one wants to eat meat in an unfamiliar place, he should inquire carefully as to the kashrus standards and supervision. Many things that purport to be kosher are not actually up to standards. Wine is another product that requires especially diligent checking.