The only Jews the entered Canaan before the main body of the Israelites where the Twelve Spies mentioned in the Book of Numbers.
"And the people marched from Haseroth, and pitched their tents in the desert of Pharan. And there the Lord spoke to Moses, saying. Send men to view the land of Chanaan, which I will give to the children of Israel, one of every tribe, of the rulers." Numbers 13:18-21, DRB
Moses gave the following commands to the spies:
"Go you up by the south side. And when you shall come to the mountains, View the land, of what sort it is, and the people that are the inhabitants thereof, whether they be strong or weak: few in number or many: The land itself, whether it be good or bad: what manner of cities, walled or without walls: The ground, fat or barren, woody or without trees. Be of good courage, and bring us of the fruits of the land. Now it was the time when the firstripe grapes are fit to be eaten." Numbers 13:1-3, DRB
After 40 days, the Twelve Spies returned with a large bunch of grapes. Of the twelve, only two had good things to say about the Promised Land. Those two men, Caleb and Josue, would later become leaders of the Jewish people. The other ten spies did not have good things about the Promised Land. Because of the lies of the ten, the Israelites murmured against God. In response, God cursed them to wander in the wilderness for 40 years.
"Your children shall wander in the desert forty years, and shall bear your fornication, until the carcasses of their fathers be consumed in the desert, According to the number of the forty days, wherein you viewed the land: a year shall be counted for a day. And forty years you shall receive your iniquities, and shall know my revenge: For as I have spoken, so will I do to all this wicked multitude, that hath risen up together against me: in this wilderness shall it faint away and die." Numbers 14:33-35, DRB
After 40 years, the Israelites were finally allowed to enter the Promised Land.