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Go directly to jail (now a tasting room) on a Maui winery tour

Where prisoners were once shackled to the wall, visitors are now free to sample fine wines following the transformation of a 19th century jail into a new tasting room in Maui’s upcountry.

At MauiWine in Ulupalakau, on the slopes of the Haleakala volcano, the history may be just as fascinating as the wines.

For more than 40 years, the company has been known for its pineapple wines, now produced in traditional and sparkling varieties.

Ten years ago, winemakers began growing new types of grapes, from which they now produce Chenin Blanc, Gewurztraminer, Grenache, Malbec, Syrah and Viognier varietals.

Those new estate wines are now sampled in the Old Jail, a sturdy structure built in the 1850s and which, for a time, held wrongdoers awaiting transportation to the county jail.

The building reopened last month after workers repaired the 3-foot-thick walls of lava rock, replaced a terra cotta tile floor and restored a koa wood bar.

Tastings in the Old Jail are part of the King’s Visit, a one-hour tour of the winery. Guides take guests to the cellar and bottling line while explaining how grapes thrive in Maui’s unique soil and the estate’s cooler temperatures.

It’s located roughly 2,000 feet above sea level, overlooking the Pacific Ocean and the neighboring island of Lanai.

The tour, offered Wednesdays and Thursdays at 4 p.m., is priced at $50 per person.

Free historical tours include a stop at King’s Cottage, built to host visits by King David Kalakaua, Hawaii’s monarch from 1874 to 1891. Inside, free samples of pineapple wines are served.

Info: MauiWine, (877) 878-6058


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