Ever since the 1800s, Lahaina has been a boisterous port town full of grog shops and places to imbibe. The same can be said for Lahaina today, although, of all the bars that pepper the town, only one has tables set out on the rooftop and a wine list compiled by a rock star.
At Fleetwood's on Front Street, you can relax on the rooftop and watch the sun set over the waters of the Lahaina roadstead. There is live music five nights a week, and occasionally the owner—Mick Fleetwood—will drop by and hop on the drums for an impromptu tropical jam.
At 5 p.m., stop in for wine tastings. Mick Fleetwood has created an award-winning "Private Cellar Collection," and there are few better venues to enjoy a glass than beneath a tiki torch in historic Lahaina.
Take in the view, sip on some wine, and enjoy the rhythms of smooth jazz or soul as they drift off into the night.