This challenge is part of the TNTina’s Trial, the second agent that Fortnite's Chapter 2 Season 2 focuses on. You'll have to visit three locations on the island: Grumpy Greens, Mowdown, and Risky Reels. The first two are much less known (and smaller) than the third, which remains a quality spawn to this day.
Map
Grumpy Greens
Hidden to the east of Pleasant Park, the Grumpy Greens are pruned into the shape of a grumpy emoji. They're much easier to spot if you look down on them when landing for example. Be careful though, as this isn't a great location for weapons!
Risky Reels
We no longer present this landmark: probably the most famous of Chapter 2. It's where the Star Wars screening event took place, and the place remains a great spawn, with many chests and materials. You'll find it west of Frenzy Farm.
Mowdown
Relatively unknown to players, this place could herald races or timed challenges later in the season! You'll find it on the heights overlooking the orchards of Frenzy Farm.
Once again, we recommend the Team Rumble mode, since you'll encounter fewer enemies. Remember that the challenge is to visit these places. Landing there or walking around will be enough to complete the challenge.