Mammals have reinvaded the sea 7 times, with 5 lineages still extant.
Cetacea (whales, dolphins, porpoises): Evolved in the Early Eocene (56 to 34 mya).
Sirenia (manatees, dugongs): Evolved in the Early Eocene.
Pinnipedia (seals, sea lions, walruses): Evolved in the Late Oligocene (34 to 23 mya).
Polar bear: A very recent adaptation.
Sea otter: A very recent adaptation.
Note: Polar bears and sea otters retain terrestrial forms but spend a great deal of time in water.
Initial adaptations involved feeding in water.
Eocene Epoch (56 to 34 mya):
Cetacea and Sirenia evolved in warm, shallow, productive seas with abundant resources.
Oligocene Epoch (34 to 23 mya):
Pinnipedia evolved when oceans had more dramatic temperature gradients and concentrated productivity.
Examples of transitional fossils:
Puijila darwini: A potential
Mammalian Locomotion & Habitat Adaptation