The first incarnation of the Careful is the Carefulwiththesteamoritwillburnyou. This ship carried Keolah and the other founding Elkandu around the world and back in time in order to retrieve the Tinean books. It was destroyed on the return trip.
The Careful II went back in time and visited the ancient Sunrise Islands, while it was an independent empire. Kitsune Tsuki stowed away, forcing them to make a hasty departure as the Imperials attempted to arrest her.
The time travel ritual that enabled the Careful to escape from the Sunrise Islands landed it near the Great Northern Ocean. It was badly damaged and dead in the water when Keolah and her group arrived, who had also been stranded in the middle of the ocean. They repaired the ship enough to limp to land.
The next ship was taken to Wilderplane using a teleport ritual after having been built in Mithim due to difficulties in locally sourcing materials and labor. Unfortunately, they discovered that the Sea of Doom really does fall off into the mists. Although most of the crew escaped, the ship itself was lost to the dark planar seas.