958/1 - Ibn ‘Umar (may Allah be pleased with him and his father) reported that the Prophet (may Allah’s peace and blessings be upon him) said: “Were people to know of what I know about the dangers of being alone, no rider would travel alone at night.” [Narrated by Al-Bukhāri]
959/2 - ‘Amr ibn Shu‘ayb related from his father that his grandfather (may Allah be pleased with him) reported that the Messenger of Allah (may Allah’s peace and blessings be upon him) said: “A rider is a devil, two riders are two devils, and three are a traveling party.”
[Narrated by Abu Dāwūd, Al-Tirmidhi, and Al-Nasā’i with authentic Isnāds; Al-Tirmidhi classified it as Hasan (sound)]
1) It is recommended to travel in company, not alone.
2) The warning not to travel alone applies to the roads that are not frequented by other travelers. As for modern-time busy routes, they do not fall under the description in the Hadīth and it is not forbidden to travel alone through them.
960/3 - Abu Sa‘īd and Abu Hurayrah (may Allah be pleased with both of them) reported that the Prophet (may Allah’s peace and blessings be upon him) said: “If three people set out on a journey, they should appoint one of them as their leader.” [Narrated by Abu Dāwūd, with a sound Isnād]
1) The wisdom behind appointing a leader in travel is that he tends to the traveling party’s interests lest they end up in a state of chaos.
2) The leader of a traveling party should be obeyed with regard to the interests of the journey, but with regard to personal matters, it is not obligatory to obey him.
3) The leader should consult his companions over matters related to their travel and not do it alone, in compliance with the verse that says: {And whose affair is [determined by] consultation among themselves.}
961/4 - Ibn ‘Abbās (may Allah be pleased with him) reported that the Prophet (may Allah’s peace and blessings be upon him) said: “The best number of companions is four, the best detachment is (that made up of) four hundred, and the best army is (that made up of) four thousand, and an army of twelve thousand will never be defeated because of their number.” [Narrated by Abu Dāwūd and Al-Tirmidhi, who classified it as Hasan (sound)] [9]
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Detachment: an army unit.
1) The best companions are those who cooperate in serving their collective interests while they are travelers or non-travelers.
2) Great numbers are not the basis for victory. Rather, what matters is sincerity of faith and patience.
Some scholars of Hadīth classified this Hadīth as weak in Isnād. It also contradicts the apparent indication of the verse that says: {So if there are from you one hundred [who are] steadfast, they will overcome two hundred. And if there are among you a thousand, they will overcome two thousand by permission of Allah. And Allah is with the steadfast.} In his Tafsīr, Ibn Kathīr said: “If they are half the number of their enemy, they may not flee from them. But if they are less than that, it is not incumbent upon them to fight them and they may turn away.” End quote.
The apparent indication of the above Hadīth is that it is not permissible for them to turn away if they number 12 thousand, regardless of the number of their enemy. This contradicts the apparent meaning of the verse.
Also, the weakness of the meaning of the Hadīth is confirmed by what was reported by Ibn ‘Abbās – the reporter of the above Hadīth – that: “He who flees from two has fled (from battle), and he who flees from three has not fled.” [Narrated by Al-Tabarāni in Al-Mu‘jam al-Kabīr]