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I think it's random, but the game is still in Early Access so if it's entirely random or maybe a bit buggy is yet to be seen.
Dragons randomly (and very rare) happen around the world, and you can bonk only girl dragons, which will deliver an egg instantly. Sometimes there's boy dragon on spot (no cuddling, no egg), for most of times noone. Easily accessed spots are balcony of Human Princess (at night), outside of Windmill at Harvest reign and hidden cliff at mountain path between Mouse city and South Kingdom.
Pirate Princess ship is travel between spots near Tavern, Beach, Golem reign and Undead reign. Maybe there's more spots because sometimes she sail out of vision. If you really want to use pirate ship, the go on kingdom map, set max day length and run around to check if maybe she will show up somewhere. Then just follow her until landing somewhere.
You can also sometimes notice normal ship at ports like Slime reign or Cat reign, but those will only travel you between North and South Kingdoms.