This once-rowdy home away from home for sailors now seems respectable—even charming. The circa-1901 hotel is a two-story plantation-style structure with big verandas that overlook the streets of Lahaina and the harbor, which is just 50 feet away. Simply furnished rooms have smallish bathrooms, mounted air-conditioners (not silent, but they do muffle the outdoor noise), and private balconies. Note that all rooms are up a flight of stairs. The quietest units face the garden courtyard—an outdoor dining area shaded by an enormous hala tree—but for people-watching from your veranda, get a room that overlooks Front Street. I recommend room no. 31, over the banyan court, with a view of the ocean and the harbor. If you want a front-row seat for all the Front Street action, book no. 36 or 49. The Pioneer Inn Grill & Bar serves a good breakfast and great cheap drinks at happy hour.