San Diego Whale Watching Cruise San Diego ranks among the world’s most incredible places for viewing marine wildlife. Between December and April, more than 20,000 gray whales migrate along its sunny coast. For the thrill of a lifetime, cruise alongside these magnificent whales in their natural environment with Flagship Cruises, San Diego’s most experienced whale watching company. Flagship’s history traces back to the world’s first whale watching cruise—right here in San Diego in 1955. Gain a deeper understanding of the ocean ecosystem and enjoy live commentary on the sights and sea creatures you encounter: gray whales, fin whales, humpbacks, minke whales, dolphins, sea lions and more. Best of all, whale sightings are guaranteed! If you don’t see a whale, your next trip is free! Tours depart twice daily aboard a comfortable, two-story whale-watching yacht, with a spacious open-air sundeck, multiple restrooms and free WiFi. Flagship’s whale-watching cruises are educational fun for the whole family.