2013 Sommelier of the Year: Alpana Singh

The vivacious owner of Chicago’s The Boarding House has devoted her career to demystifying wine.


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“This is the story about a girl named Lucky” opens the self-penned Twitter bio of Alpana Singh, M.S. “Proprietor of The Boarding House Restaurant & Wine Bar, Master Sommelier, Pug Lover.”

Singh nailed down her creds early on, and it was hard, dedicated, determined effort—not luck—that made it all possible. 

At 23, she was named sommelier at the acclaimed Everest Restaurant in Chicago. Three years later, she earned her Master Sommelier credentials, and soon after became the host of the popular PBS restaurant review program, Check, Please! (She’s recently retired after 10 seasons on air.)

The California native co-founded Chicago’s The Boarding House restaurant in 2012, where she presides over a generously stocked wine cellar that showcases her wide-ranging and curious palate. Singh’s an exceptional educator, happily sharing her wine knowledge via speaking engagements, classes and special tastings at the restaurant.

In a phone interview punctuated by her infectious chuckles, Singh confesses that she was told in the early days that it was a pipe dream to become a Master Sommelier.

“There’s some stubbornness on my end,” she says with pride. “I never pursued it to say, ‘I’ll show you.’ I was just extremely fascinated by it. 

“The most difficult thing for me is that hoity-toity thing that sometimes gets attached to wine,” she says. “I almost have to white-knuckle it at the dinner table, or say something inappropriate just to break the tension.”

The Boarding House wine list gives patrons a peek into her playful nature. Chenin Blancs from South Africa and California appear under the headline “Loire Valley Love Letters.” Austrian wines are grouped under “Grüner & The Gang.” 

It’s easy to see why one of the FAQs on the restaurant’s Web site is “Will Alpana actually be at the restaurant?” She’s the person that people want to meet. And the answer is yes, she almost always will be.

“I think it has to do with my early experience waiting tables, very much as a novice, trying to learn about wine,” she says. “Having been in that situation, I developed empathy toward people starting out. 

“The amount of knowledge required brings humility,” she says. “I think it should also be fun, but not dumbed down at all. I like connecting the dots for people—especially in the restaurant business, where there are so many cultural differences.”

Never one to rest on her past achievements, Singh recently took up running and completed her first half-marathon. The goal—there’s always a goal to be pursued—is to run the 2014 Chicago Marathon. 

“Somms like to always look for that next challenge,” she says. “They’re people that are naturally driven, and being told you can’t do it attracts them to that exam. That’s what connects us—we all have this amazing pursuit of the pursuit.”

For her passionate pursuit of knowledge, her inspiring leadership and her engaging, good-humored approach to wine, Wine Enthusiast is pleased to honor Alpana Singh as our 2013 Sommelier of the Year. 

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