I had heard about these tours in the past, but since we had never tried one before, we decided to stick with a standard tour of Tremont. Nick and I used to live in Tremont, and being an architect, Nick knew a lot about the history and architecture of Tremont, so we weren't exactly expecting to learn anything new, but in fact, WE DID! Our tour guide was very knowledgable and led us around parts of Tremont for 3.5 hours.
If I were to summarize the experience, its like a walking tour meets progressive dinner. We met the group at 4 pm in Lincoln Park, and from there, we stopped at 4 restaurants: Prosperity Social Club, Parallax, Ty Fun, and Lilly Handmade Chocolates, although the stops are subject to change with each tour. In between eating delicious food, we learned about how Tremont came to be, and some fun facts about the neighborhood as well as the restauranteurs. Alcohol was not included in the standard tour but was available for purchase, although you can do a custom tour that includes alcohol as well.
Overall, a very fun experience, and one that I highly recommend. This would also be a great gift for Father's Day, or in general a fun gift for someone who has everything. You can make your tour reservations here.
As I mentioned previously, it is a walking tour, so comfortable shoes are key. Unfortunately, I have plantar fasciitis, so walking for 3.5 hours in flats will absolutely destroy my feet. Lucky for me, I found this pair of flats that are not only cute, but offer the kind of arch support I need.
At $99 they are a little expensive for flats, but they are worth it considering I will wear them all summer with zero pain!
So there you have it-- a lot of food and a little fashion to get your week started off just right!