The phrase "A Land Flowing with Milk and Honey" appears in the bible more than 20 times, always in a very favorable context, as a land rich and nurturing beyond imagination.
"And I am come down to deliver them out of the hand of the Egyptians, and to bring them up out of that land unto a good land and a large, unto a land flowing with milk and honey..." - Exodus 3:8
"Hear therefore, O Israel, and observe to do it; that it may be well with thee, and that ye may increase mightily, as the LORD, the God of thy fathers, hath promised unto thee—a land flowing with milk and honey." - Deuteronomy 6:3
And then there's Isaiah.
When he talks about an abundance of milk and honey, in his prophecy about the Assyrian attack on the Holy Land, it's clear that he's referencing this famous idiom, but the context is completely backwards:
"In that day shall the Lord shave with a razor that is hired in the parts beyond the River, even with the king of Assyria, the head and the hair of the feet; and it shall also sweep away the beard. And it shall come to pass in that day, that a man shall rear a young cow, and two sheep; and it shall come to pass, for the abundance of milk that they shall give, he shall eat curd; for curd and honey shall every one eat that is left in the midst of the land. And it shall come to pass in that day, that every place, where there were a thousand vines at a thousand silverlings, shall even be for briers and thorns. With arrows and with bow shall one come thither; because all the land shall become briers and thorns." - Isaiah 7:20-24
What kind of milk? What kind of honey?
To understand Isaiah's reference we must first understand these two products in biblical terms: both were naturally occurring and have been forming way before mankind realized it can regulate its manufacturing, and not just gather it when it's available.
When man realized he too can enjoy animal milk, he started to maintain herds, and to figure out the right conditions to make their milk flow abundantly, i.e. lush vegetation. Bees produce honey in order to nourish their next generation, and keep it in hives, hidden deep in the wild, in hollow trees and crevices. They also need to settle in the vicinity of some flowering plants, from which to collect nectar. In other words, the same conditions apply in areas that make both the milk and the honey flow: wild and rich in vegetation.
The Jewish sages from the first few centuries C.E. tell of bee-keeping, but in the Bible it's never mentioned, probably because people haven't figured it out yet. Back then, honey was considered a treat you might stumble upon, a kind of "finders keepers":
"Hast thou found honey? eat so much as is sufficient for thee, lest thou be filled therewith, and vomit it." - Proverbs 25:16
Or after Samson's fight with the lion:
"And after a while he returned to take her, and he turned aside to see the carcass of the lion; and, behold, there was a swarm of bees in the body of the lion, and honey. And he scraped it out into his hands, and went on, eating as he went, and he came to his father and mother, and gave unto them, and they did eat..." - Judges 14:8-9
These describe honey as something that does not belong in well-manicured farms and fields but in the wild outdoors.
Bee vs. Date
There is an interesting question here, regarding the source of the honey. In several instances it seems more plausible that the Bible is referring to honey made from dates, and not bee honey. Opinions differ to this day, both among modern researchers and the ancient sages. Rabbi Akiva for example, was certain that the "flowing honey" belonged to bees, but he had quite an opposition.
Deuteronomy 8:8 counts the seven native crops of the Promised Land: "a land of wheat and barley, and vines and fig-trees and pomegranates; a land of olive-trees and honey." Other than the first two grains, all the rest are fruit, and since these are all cultured crops and we know people weren't keeping any bees at the time, it makes sense the "honey" is also a fruit.
Another example is the report made by the tribal leaders Moses sent out to survey the Promised Land before entering:
"And they told him, and said: ‘We came unto the land whither thou sentest us, and surely it floweth with milk and honey; and this is the fruit of it." - Numbers 13:27
The proximity of the words "honey" and "fruit" may suggest that they are in fact related.
One of the things I like most about text studies, is that you don't really need to come up with a definitive answer; both versions have value in telling a story. If indeed the "land flowing with milk and honey" was referring to goat milk and date honey, then it's a way of saying the land has both lush wild areas for shepherding AND areas that allow for agriculture. I like this reading very much, and in my personal opinion, the description of the seven crops indeed refers to dates.
However, if it were the case across the board, than why would Isaiah use a symbol of agriculture and prosperity to paint his prophecy of a land that "shall become briers and thorns."?
Forest vs. Civilization
If we go with bee honey, this makes more sense: Isaiah is talking about the destruction of civilizations as a result of the Assyrian invasion, and the subsequent takeover of wild vegetation. Other prophets have used this image as well:
"... And Jerusalem shall become heaps, and the mountain of the house as the high places of a forest." - Micah 3:12
"And I will lay waste her vines and her fig-trees, whereof she hath said: ‘These are my hire that my lovers have given me’; And I will make them a forest, and the beasts of the field shall eat them." - Hosea 2:14
And also in a historic depiction in the Book of Maccabees, when the Jewish rebels discover what had happened to their temple:
"There they found the sanctuary deserted, the altar desecrated, the gates burnt down, and vegetation growing in the courts as it might in a wood or on some mountain, while the storerooms were in ruins." - 1 Maccabees 4:38
We see that as far as these prophets were concerned, a forest (the place we know to be flowing with animal milk and bee honey) is really a symbol of great destruction and the doom of civilization.
How does that settle with the magnificent descriptions of the Promised Land?
Let's take a closer look at the story of the tribal leaders Moses sent into the land to survey it. The report, as we have just seen, was full of amazement: finally, a green, lush land after 40 years of scarce desert thorns. But along with that came great fear:
"The land, through which we have passed to spy it out, is a land that eateth up the inhabitants thereof; and all the people that we saw in it are men of great stature." - Numbers 13:32
Where did this creepy "land that eats up its inhabitants" come from? Actually it may well be a direct description, since we know the forests at the time were crawling with predators.
"...And there came forth two she-bears out of the wood, and tore forty and two children of them." - 2 Kings 2:24
Forest dwelling animals - bears, lions and boars - would occasionally come out to hunt, and a number of famous biblical figures have encountered them. The tribal leaders sent by Moses may have heard or even seen these animals, and felt as if the land might literally devour them, and that only giants might have a chance to survive in such a wild territory, a land flowing with milk and honey.
We must remember that in those days, the fertile valleys were already inhabited by pagans, so the area available for the Israelites to settle was the rough, wild mountain range. Eventually they established a flourishing agricultural society up there, and pushed the predators away.
Following the destruction, the Assyrians brought over foreigners, to settle the deserted Israelite cities:
"And the king of Assyria brought men from Babylon, and from Cuthah, and from Avva, and from Hamath and Sepharvaim, and placed them in the cities of Samaria instead of the children of Israel; and they possessed Samaria, and dwelt in the cities thereof. And so it was, at the beginning of their dwelling there, that they feared not the LORD; therefore the LORD sent lions among them, which killed some of them." - 2 Kings 17:24-25
After the Assyrians destroyed the towns and fields, and the land reverted to "briers and thorns", the predators returned and were able to pick off the occasional newcomer. No wonder Isaiah said in his vision that "With arrows and with bow shall one come thither" - for fear of the roaming predators.
And so, according to Isaiah, the land flowing with milk and honey is also the land that devours its inhabitants.
A Note on Egypt
Another strange use of "a land flowing with milk and honey" appears during the long years in the desert, when the people complain to Moses:
"...is it a small thing that thou hast brought us up out of a land flowing with milk and honey, to kill us in the wilderness..." - Numbers 16:13
They are claiming that he has taken them AWAY from a land flowing with milk and honey, i.e. a land full of thick wild woods, but as we all know, Egypt, with its Nile and its delta, was the very embodiment of agriculture.
The answer lies in the instructions Josef gave his brothers, when they came down from the famine-stricken Canaan to seek refuge in Egypt:
"... when Pharaoh shall call you, and shall say: What is your occupation? that ye shall say: Thy servants have been keepers of cattle from our youth even until now, both we, and our fathers; that ye may dwell in the land of Goshen; for every shepherd is an abomination unto the Egyptians." - Genesis 46:33-34
The Egyptians hated shepherds because of the damage their animals cause their fields, so it followed that the historically herd-owning Israelites would be allotted a place like Goshen - a distant piece of land, away from the fields, that would have plenty of natural vegetation for the animals; a land flowing with milk and honey.
The phrase "A Land Flowing with Milk and Honey" describes areas that are untended by man and covered in wild vegetation. So long as the Israelites made their living off of animal husbandry, it signified the promise of a rich, comfortable life. But once the forests were cleared and the people settled and started working the land, it became a dire warning.