Tom has more imagination than Huck, which allows him to come up with all kinds of elaborate games and crazy schemes. Unlike Huck, Tom lives in a relatively civilized environment and so can afford to dream without fearing the consequences. Among other things, this means he can take more risks. Huck, on the other hand, is more cautious, because he's lived practically his whole life on the margins of society.
Huck tends to defer to Tom for coming up with ideas for fun and excitement. Huck knows that there's no way in a million years he'd ever be able to devise anything as ingenious as what his best friend comes up with. We see this when Tom comes up with a daring escape plan for Jim. Huck knows it's dangerous and that they could all get into serious trouble, but he goes along with Tom's plan because, as well as being more "stylish" than any potential plan of his own, it's also pretty exciting.
Huck is a far more pragmatic boy than Tom Sawyer, and so Tom's "adventures," such as the raid on the Sunday school picnic in chapter two, are faintly ridiculous in Huck's eyes. He does, however, value Tom Sawyer's friendship and social connections with other boys, so he goes along with it, even though he knows they aren't really "highwaymen" and that the spoils won't be treasure but only doughnuts and jam.
Late in the novel, Tom Sawyer's insistence on the convoluted plan to "free" Jim is another matter altogether. His toying with Jim and the Phelps's at their farm is cruel and unnecessary, but for Tom, it is the pinnacle of his adventures with Huck. Tom oversees what amounts to "gaslighting" Aunt Sally and needlessly delays Jim's legitimate freedom for his own entertainment. Huck goes along with Tom's games because he does not feel like he can challenge his apparent social superior. He does, however, rein Tom in somewhat from the more egregious things he intends to make Jim endure.
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