Built in 1901 and perfectly located, the historic Pioneer Inn may look salty and sea-worn at first glance, but step inside for a pleasant surprise. The 34 rooms are modern and many have direct access to the wide 2nd-floor terrace. The accommodating staff keep the sailing smooth. Ship figureheads and the saloon’s swinging doors give a nod to Lahaina’s whaling past.
To avoid noise from Front St, ask for a courtyard room. All rooms are on the 2nd floor, with no elevators. Rates hover closer to $175-200 outside of the high season.