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Thirsty Thursday: Bar Siena

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Here in Chicago, I am pleased to announce we have assembled a new team! So when myself, Julie, our new co-editor, and Brittani, our new Social Bitch, decided to get together, we all agreed it should be over post-work drinks. I chose Bar Siena because of it’s proximity to where a few of us where to be around that day, and because grabbing wine and pizza seemed like an ideal way to get to know each other. We didn’t end up indulging in pizza, but we did indulge in cocktails instead, thanks to the assistance of our lovely bartender, Stuart.

Bar Siena

The Vibe

I had never been upstairs in Bar Siena before and the three of us were in awe of how lovely it was. On the first floor, Bar Siena hosts a large encompassing bar that is the focal point of the restaurant, and tables for guests to sit and eat. Upstairs is an atrium style dining area with a surrounding balcony in the center that looks down to the bar below on the first floor. Additionally, a grand tree of branches lit with beautiful tiny lights grew up into the second story though the center opening. It had a magical element.

Bar Siena is an upscale pizza and wine spot, but the space it self is fit for any type of gathering or occasion. The lighting is dim and romantic, and the upstairs provides private booths in a quieter area away from the hustle and bustle of the bar below, where patrons sit and eat, or sip cocktails while anxiously awaiting a table. Yes, one should expect a wait typically.

Is this Seat Taken?

My friend Stuart is a bartender at Bar Siena, so when I discovered he was working on the day of our planned get together I thought it would be a great idea to go somewhere where we could get a little VIP service, as in a private section of the cute bar located on the upper level of Bar Siena where he was working that day. A private party was gathered in a closed off section, but the service bar is perfect for sitting and enjoying libations. Thanks to Stuart reserving four seats for us, it really did feel like a private tasting bar, truth be told. It was fun watching Stuart make cocktails with the gorgeous copper bar tools, from shakers and bar spoons, to strainers and jiggers. I wish I had Bar Siena’s essentials in my own home bar collections.

As I mentioned before, the bar downstairs is consistently busy and it is full of patrons squeezed in close together, while others continue to circle around eyeing for the next space to become available as they wait for their table. It is not the most intimate of settings, and while fine to stand and converse while waiting to be seated, it is not ideal for intimate conversations. Having never been upstairs it was a delight to find a retreat from the albeit jovial, but chaotic vibe downstairs.


In my previous visits to Bar Siena, I have always enjoyed wine. Today though, the ladies and I decided to get to know each other cocktails, making it a great opportunity for a Thirsty Thursday post. Being a Monday, we didn’t get too crazy indulging in libations, but instead chose to follow Stuart’s lead and go with his suggestions of the best of the best cocktails, according to what we each like.

Bar Siena

The cocktail menu is surprisingly extensive, with concoctions of all sorts that enticed us. A fan of Knob Creek, Julie decided to go with the #4, something Stuart described as a “warmer Italian-style Old Fashioned”. Not warmer as in temperature but warmer as in more “thermal” of a drink, I would say. Not as strong or harsh as a typical Old Fashioned can be, but lighter. The #4 is sweetened with an amaro as opposed to sugar, giving a slight bitterness to the drink. What truly warmed it up was the syrup of winter spices. Hints of cinnamon, cloves and cardamon made the drink especially fragrant.

Bar Siena

Brittani went with Stuart’s recommendation of his favorite cocktail on the menu, the #13.  Made with Bombay Sapphire, this was a light and citrus-y drink that was appropriately served in a coup glass, as it was frothy on the top. Everyone was a fan of this cocktail. The lime, pineapple juice, and patron mango worked well together; while not too sweet, they provided for the perfect amount of fruitiness.  A hint of mint could be identified and added to the freshness of the cocktail. What was especially lovely was a spicy finish on the back end thanks to the serrano peppers.

Bar Siena

A fan of the Aperol Spritz, especially in summertime, I went with Stuart’s suggestion of the #5, which I had already been eyeing. Made with aperol, lillet rose, lemon, thyme, tonic, it was a sweet concoction that was reminiscent of the apertifs I had so often on my visit to Italy one summer.  Seeing that we were in an Italian restaurant, it seemed especially fitting. What I loved about this drink was its herbaceous character, thanks to the addition of thyme. It was refreshing, not overly sweet, and went down a little too easily in my opinion.

Bar Siena


Pop into Bar Siena for a post work cocktails, pizza and wine, or a midnight hour night cap. The bustling atmosphere is a clear indication of Bar Siena’s immense popularity, but despite it being a hit pizza and wine bar, we were thoroughly imressed with the cocktails.p

Bar Siena
832 W Randolph St.
Chicago, IL

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