First things first: this is an incredibly beautiful space for a wedding. We held our ceremony on the roof deck, which was gorgeous even in pouring rain (and our guests were dry), and our cocktail hour in the outdoor wine garden and dinner insid...e. The spaces were all perfect, our guests had an amazing time, and the food and wine was superb as well. We really felt like we lucked out in terms of the space and the food: the day itself was really magical, and it was a great experience for our guests, because the venue itself had such a great setup and food/drink.
But we also felt extremely disappointed in the lackluster service that we received from City Winery's staff, especially given the very sizable administrative fees. We first started planning our wedding with Colleen, and signed the contract with her because we felt so confident in her work; unfortunately, she soon afterwards left City Winery and we began to work with Brittany, who seemed solid. We had been promised by Brittany that we would be working primarily with her, given that we had been working with Colleen before, but soon found ourselves passed off to another planner whose competence was constantly up in the air: she never seemed to be well-organized in our conversations and meetings, and we had really no confidence in her ability to pull off our actual wedding day. Communication in advance of the wedding was rough, and we constantly had to follow up on requests to make sure that they were actually implemented. We were extremely glad we had hired a day-of planner, who took careful notes in our meetings and made sure everything ran smoothly at our wedding, because we had lost confidence in City Winery's staff by the time our wedding came.
Due to this issue, there were also several major issues that came up during our wedding. City Winery's dessert sweet bites were included in our package, but we made emphatically clear that the important part of our dessert was the beautiful cake that we had ordered from an outside baker. Nevertheless, City Winery's staff seemed totally incapable of serving our cake: the catering crew plated it on random tables and as a result, probably 2/3rds of our guests did not receive cake, nor even knew it existed.
Similarly, there are some real mysteries regarding the space itself: we had been assured for months that the elevator would be working, but it still was not on the day-of, and our guests took a catering elevator that had to be run by an attendant -- it was not only an eyesore, but also not properly staffed. (The staircases between the floors were also wet, slippery, and pretty ugly.) Given that this is a wedding venue, we would have expected these and other issues to be much better worked out by now. But it was really the staff that was the disappointment: I would certainly recommend City Winery for your wedding, but with the hopes that there is a more competent administrative team in charge, and with the recommendation that you hire your own day-of coordinator.