The late, great British illustrator, Ronald Searle was sometimes sent to draw on location for Holiday Magazine (also late, great) and had a strategy for sketching in a new town when he had limited time. What he'd do is go immediately to the town's center, find a gift shop, and then buy the postcards of that town. He'd then seek out those places and sketch at those famous places. He didn't want to miss the the town's most important sites.
As for me, I tend to do the opposite. In a new town, I wander off and look for the under appreciated or the overlooked. The undrawn. I do that by instinct more than strategy. I don't like to draw a crowd when I'm drawing a picture. I'm too self conscious for that. I'm too unsociable. Also, I'm simply drawn to the outskirts. I like to get away from the other tourists. I want an unobstructed view of my interest, like I had this day in Tuscania, Central Italy.
Like Robert Frost wrote in his famous poem, The Road Not Taken:
...Two roads diverged in a wood, and I—
I took the one less traveled by,
And that has made all the difference."