Calypso's Island was the longest stop Odysseus and his men had. They were here for 7 years because Calypso immediately fell in love with Odysseus and did everything she could to have him for herself. She tried to get him to stay by telling him he could be immortal. Hermes was sent to tell her to let him go and he left on his journey which was far from over.
The Cyclops' Island
At the land of the Cicones 75 of Odysseus' men died. They were being very reckless and when Odysseus told them to stop they didn't. Part of this was because of how drunk they were. They were punished by Zeus with two storms. On the the storms sent them off course 9 days.
On the island of the Lotus eaters Odysseus send 3 of his men to explore the island and see them men that lived here. The men ate a lotus plant which causes them to forget their homeland and loose track of time. Odysseus has to go out and find them and bring them back to the ship where he had to tie his men up.
Land of the Dead
Here's your prophecy
Odysseus decides to go to Polyphemus' island because of his curiosity. Odysseus and him have a conflict and Polyphemus starts eating his men. Odysseus ends up playing a trick on him to help them escape. He also blinds him so that they can escape without him noticing. Odysseus provokes the cyclops once off the island which causes Polyphemus to ask his father Poseidon to put a curse on him and his men.
Odysseus and his curiosity get the best of him when he sends 23 men out to explore Circe's Island. His men were being devious and sneaking around when they find Circe. She set a trap up for them so she can turn all of them into pigs. Hermes gives Odysseus a root so he can't be turned into one too and he can save his men. He stays here for a year.
Eat this it'll protect you
Circe sends Odysseus to the Land of the Dead to get his prophecy. He first has to make three sacrifices. He than gets his prophecy from Teiresias that states he have a long journey on sea where all his men will die, when he returns home there will be suitors trying to marry his wife, and he has to make a sacrifice to Poseidon. All of this will ensure him a peaceful death at an old age when he returns home.