We just got back from the most relaxing and enjoyable trip to Chicago and to a little town called Destination Kohler, near, Sheboygan, Wisconsin…random, right? It totally was, but also completely amazing. My mom, Charlie and I tagged along with Will, my dad and their friends on their golf trip to Wisconsin and I am so glad we did.
Since we were barely in Chicago, this is by no means an all-encompassing guide to the city, rather just a quick taste of the town. My guide to Destination Kohler and Sheboygan is a bit more comprehensive.
Because we could all get nonstop flights into Chicago, we decided to start our trip and celebrate my mom’s birthday with 24 hours in Chicago. We stayed at the Fairmont Millennium Park, which was nice, but I didn’t love it and am not sure if I would stay there again.
Since we knew our time was limited, we hit the ground running as soon as we landed. We picked up a deep dish pizza from Giordano’s which was around the corner from our hotel and had a picnic lunch in Millennium Park (home of the infamous Bean). I know there is a heated debate about deep dish pizza in Chicago, but honestly, I will eat any pizza, any time so I was just happy to try one of the many famed establishments. Pro tip: order your pizza ahead of time online because they take about 50 minutes to cook.
Once we were done with our lunch, we walked from Millennium Park over to Navy Pier, where we boarded a boat for the Chicago Architecture River Cruise. This is my absolute FAVORITE thing to do in Chicago because I love being on the water, but I also love learning about the Chicago architecture. It is truly stunning and all of the boats have a bar so there is no better place to spend the afternoon in my mind.
We celebrated my mom’s birthday while we were in Chicago and had the most delicious meal at RPM Steak. We all loved the food and the service was incredible, but the music was really loud and the vibe was something like what I would have been into in my early 20s. I would highly recommend it and also suggest trying Bavette (and making reservations early!)
The main part of our trip was spent in Destination Kohler–an idyllic town outside of Sheboygan, Wisconsin. The area is well-known for its golf–Whistling Straits and Blackwolf Run which each have multiple courses within them, and the Kohler Waters Spa.
Although the beginning of our trip was a bit stressful–we were staying at the Inn on Woodlake which at the time legitimately seemed like a frat house for golfers, and my mom, Charlie and I were getting a lot of unwanted attention, by the end of the trip, we were all raving about how we had the best time. My mom and I relaxed, went paddle boarding, did two days at the spa (if you’re getting a facial or a manicure, ask for Dawn–she is incredibly talented and a truly wonderful person), went shopping at Sweet Potato’s and the Woodlake Market (I live for a good grocery store) and we are already planning our return trip.
Where to Stay:
My husband booked our stay with a golf package so we could only stay at the American Club or the Inn on Woodlake. By the time we booked, the rooms at the American Club were fully booked. The next time we go, I definitely want to stay at the American Club rather than the Inn on Woodlake. If you’re not planning to book through a package and just want to explore Sheboygan, I would suggest the Fairfield Inn or the Grandstay hotel.
- The Kohler Waters Spa
- Paddle Boarding on Woodlake
- Lunch at Deland Park on Lake Michigan
I know we just barely scratched the surface in terms of activities, but my mom and I really enjoyed ourselves and didn’t want to over do it. Obviously the boys golfed so we took full advantage of the spa and the recreational activities at the Sports Core on Woodlake which included paddle boarding. I would also recommend stopping by Sweet Potato’s for some retail therapy. They have everything from Birkenstock’s to Vince and CBD oil–mom and I loved so many things there.
One of my favorite activities wasn’t exactly planned, but we kind of stumbled upon it. After our massages one day, mom and I were both craving just a really simple sandwich so we picked up Jersey Mike’s and then my mom had the brilliant idea to eat it by the lake. We discovered Deland Park which is a beautiful park right on Lake Michigan. Lots of green space and even beach access so we had a gorgeous lunch and Charlie loved running around.
Where to Eat:
- Trattoria Stefano
- Il Ritrovo
- The Wisconsin Room
- The Horse and Plow
- Whistling Straits Restaurant
- The Woodlake Market
- Blackwolf Run Restaurant
The food really blew all of us away on this trip. I asked our group after to rank our meals and it was nearly impossible because we enjoyed each one so much. In my opinion, I guess I would have to say my favorite breakfast was the burrito at Whistling Straits and my favorite dinner was at Trattoria Stefano–the food was delicious and we had the best waiter. My mom and I loved grabbing coffee and snacks from the Woodlake Market and lunches at the Horse and Plow were so good! Our waitress there even showed me the most delicious trick–dipping sweet potato fries in honey–genius!
Truly the best trip! I am so thankful for the new memories made with my parents, Will, Charlie and our friends and I can’t wait to go back to Destination Kohler!