What You’ll Find Inside This Ancient Hawaii Jail Is Unexpected But Awesome

On the slopes of Mount Haleakala - on the beautiful island of Maui - sits an old, single-room stone cottage once used as a jail. However, while the building’s history is truly fascinating, it is what you will find there today that will truly enchant you. You see, the small cottage sits atop the Ulupalakua Vineyards, and is now the site of an exclusive wine tasting offered by the famous MauiWine.

In the land of umbrella drinks, it can be tough for a wine lover to find a glass of good wine, but in beautiful Kula, MauiWine is truly in a class all it’s own - and that’s not just because you’re able to drink estate wines out of an old jail cell on the property.

The cottage was built in the mid-1800s, and served as the office for James Makee, a former whaling captain turned rancher and sugar plantation owner. Now situated behind the bar, and accessed via a staircase through a trapdoor in the floor are the remnants of what was used as a makeshift jail cell.

If you’re hoping for stories of great crime and intrigue, look elsewhere, for this jail is notorious for housing far less sinister individuals. You see, in the late 1860s, the Makee family began throwing lavish parties full of dancing, singing, parades and even horse racing. Party attendees including notable island families, seamen from warships docked in the nearby Makena Bay, and even, in 1874, King Kalakaua and Queen Kapiolani. When these events got out of hand, as most parties seem to, the cell beneath the floorboards housed unruly revelers until they sobered up - some even shackled to the wall.

The "Old Jail" - as locals fondly refer to it - was also used as a holding cell for wrongdoers awaiting a transfer to the county jail.

The ownership of this land changed hands twice in the next 100 years before becoming established as a winery in 1974, and what the small jail cell was used for during that century can be left to your imagination (as I can’t find any relevant information proving any one story).

The impromptu jail tours are offered almost daily for $15, and in addition to a tour of this charming cottage and the surrounding grounds, guests are able to taste three estate wines not offered elsewhere at the vineyard.

MauiWine is located at 14815 Piilani Highway, Kula, HI 96790 and is open daily from 10:30 a.m. to 5:30 p.m., with free grounds and wine-making tours offered at 10:30 a.m. and 1:30 p.m. daily.

If possible, be sure to spend some time in jail the next time you make your way to the beautiful island of Maui - there is truly nothing quite like the experience you’ll have. And if you’re a wine aficionado like me, be sure to check out these vineyards and wineries found across the Hawaiian Islands.