Oswald learns that the "Captain Cook" he's looking for (where the girl is) is a statue. He finds it, and he finds her. "Wonderful day for tanning," he says sarcastically as she sops in the rain. She hands him the next clue, which sends him looking for a bushie. Meanwhile, Alex finds the kid on the trike, and Dave finds Captain Cook. Oswald needs a little more help finding the bushie, which he gets with no trouble. He flashes a truly gorgeous, glorious smile as he takes off.
Blake finds the surfie and gets the clue. However, he is (as he himself interviews) in such a hurry that he doesn't read the directions (and apparently didn't read them at the beginning), so he immediately goes back to the opera house to find Paige. Wil, meanwhile, also finds the surfie -- and proceeds to do exactly the same thing. Tara isn't really sure that Wil did it right, but of course the person they run into at the opera house is Blake, who tells them that he did exactly what Wil did. Ha! This is awesome. Taraweasel and the Teeth take off in cabs, looking for the ankle-biter. Yeah, they've screwed it up all right. Chris, meanwhile, is very suspicious of how Blake and Wil could have beaten Alex and Dave (who experience would suggest are better at Roadblocks than Wil and Blake) back to the starting point. "How the hell did Blake find something first?" Chris wonders. "He's an idiot." Hee! Umm...Chris is showing his shoulder here, too. Oh, dear me. His elbow has a dimple. BAH! All of a sudden I have issues! I have bouncer issues! I have arm issues! Crap.
A sopping wet Oswald finds the bushie, who has a big cockatoo on his arm. The clue he hands Ozzie tells him that NOW he can return to his partner and go check in at the pit stop, which is on the roof of the Museum of Contemporary Art. Way to go, Oswald, you thinker, you.
At the pit stop, Phil tells us that the first team to get there will win a seven-day Caribbean Cruise. Wow, nice.
Dave finds the swimsuit girl, and though he's in a hurry, he's not in too much of a hurry to tell her she's "looking fine" in a way that calls to mind the last few minutes of Ferris Bueller's Day Off. Next, Alex finds her. Oswald, meanwhile, makes it back to Danny. They quickly hoof it to the museum, run up to the roof, and land on the mat. Woo-hoo! They're greeted by the town crier, who is very cute and rings a big noisy bell, and yells, "Welcome to Syyyd-neeeeey!" Phil tells them they're in first place. They hug Phil, and he loves them. Wow, they rocked the hell out of this leg of the race. Pretty much mistake-free in every way. Weirdly, we don't see Phil tell them about the cruise. Hmph. Wouldn't you have liked to have seen that? Don't you suspect they were happy? Double hmph.