As you walk into the entrance way of the Kinn Guesthouse, you’ll find a beautiful open kitchen that faces a large couch, conveniently placed next to a cozy fireplace. As you enter, you instantly feel as though you’ve walked into a close friend’s home. Decorating the wall behind the couch is a broad collection of art displayed in a gallery style. If you look close enough, you’ll find two black and white portraits of men hidden among the colorful bustle of art. These men are the grandfather and father of Charles Bailey, the same men that ran The Drake Hotel in downtown Chicago and The Drake in Oakbrook, respectively. Now that Charles has opened his own guesthouse with his wife Connie Bailey, they thought it fitting to name their business Kinn (adding the extra “n” because the building is on Kinnickinnic Avenue in Bay View).
Originally from Chicago, Charles was a floor trader for years. But as the industry changed, he started looking at other career options. “I’ve always been fascinated with the idea of hotels because I’ve been around them my entire life. I never thought I’d be in the business but it always intrigued me,” says Charles. The couple lived in Chicago’s Wicker Park neighborhood until they decided it was time to move as their son, Quinn was getting older. The family moved their life to Milwaukee and soon after that, found a beautiful brick building in Bay View for sale.
“The building presented itself and our dream started to take shape,” Connie explains. “The concept was all Charles, but we did work together to perfect the idea and execution.” The couple put in a great deal of work to get the building to where it is now. It started out as a masonic lodge then a series of bars and restaurants that didn’t take care of the space. Connie and Charles gutted the entire thing and brought the building back to life, while keeping the original flooring (110-year-old maple) and exposing the cream city brick walls.
Charles was always interested in the idea behind Airbnb and foresees the company changing the hotel industry. “To me, the success of Airbnb means that people care to live in a different way. They want something that feels more like home than the big hotels,” he says. Charles found the perfect mix between that homey concept and the luxury feel of hotels: comfy but not too personal. “Usually you just want to live like you do at home [when traveling],” says Charles. “I didn’t have to prove that concept, I just had to build it.” The idea was to keep overhead low by making the building totally self-sufficient so that Charles and Connie could focus on enriching the rooms as much as possible. When you book a room with Kinn Guesthouse, you receive a code for your room that becomes active the day you check in. When you arrive, your room is ready, there’s community wine in the common room, and if you happen to be there on a Saturday morning, Charles is most likely there to greet you with fresh muffins from Honey Pie (the bakery next door).
Kinn Guesthouse opened in March of this year but it is already very involved with theMilwaukee community. On all the walls in the guesthouse, you will find artwork from local Milwaukee artists that Connie handpicked herself. The exception is the gallery wall in the common room, which is part of Charles and Connie’s personal art collection. Connie plans on swapping the artwork in the rooms to display more local artists. On the Kinn website, you can find links to these artists. Kinn is also working with the restaurant Kindred, located on the first floor of the building. “We are starting to create events that bring local vendors in for conceptual dining experiences,” explains Connie.
Kinn makes it easy for travelers to instantly connect with Milwaukee. Guests can enjoy the luxurious day-lit rooms while feeling like they’re at home with access to a kitchen and a bottle of wine waiting for them on the counter. And the best part is that Charles and Connie take the time to get to know their guests. View their website and take a peek into the Kinn Guesthouse.