Pioneer Inn Grill & Bar

Lahaina, with its many Victorian flourishes, may look picturesque today, but the port town teemed with sailors, gamblers, and prostitutes in the 19th century. The Pioneer Inn changed all that when it opened for business in 1901, foreshadowing the tourist industry that would ultimately replace whaling, sugar, and pineapples. Step through the swinging doors of this vintage bar, which now bizarrely anchors the courtyard of a Best Western, and you’ll be transported back in time. Oars, harpoons, and a ship’s figurehead still adorn the space, looking down on platters of coconut shrimp, Parmesan-crusted fish over coconut rice, and margaritas made with POG (a mix of passion fruit, orange, and guava juices). Come during happy hour, which runs daily from 3 p.m. to 6 p.m., for discounted beers and cocktails.

Although it might look like another tourist town, Lahaina during the 19th-century was the Wild West of the Pacific. Despite the fact that Christian missionaries managed to convert the royalty, this teeming port town of whalers and seamen was riddled with brothels, gambling, and sin. Prior to 1901, Lahaina was a town without an inn or any form of hotel. Tourism wouldn’t hit Maui for another fifty years, and if a sailor spent a night on shore, it was probably because drunkenness or lewd behavior had earned him a night in jail. That all changed when the Pioneer Inn opened its doors for business. Located between Front Street and Lahaina Harbor, it would foreshadow an economy that would ultimately replace whaling, sugar, and pineapples. Although tourism has taken over Lahaina since the Pioneer Inn first opened, you can still experience the early days when you enter through the bar’s swinging doors. Old harpoons adorn the walls in the interior of the wooden bar, and nearby, in the hotel lobby, you can read the original rules of the house which include “If you wet or burn your bed you going out.” Every Wednesday from 3-8 p.m., there is a fascinating exhibit called the “Story of Lahaina,” which details the history of the town. A modern piece of Maui’s history, the “P.I.” has been visited by generations of patrons searching for a cocktail or beer. It’s a classic choice for grabbing a drink when making your way across town.