Josh and Haley Wallin are the kind of cruisers who make you want to drop everything and cast off the lines. Aboard SV Slacker, their 1986...
Josh and Haley Wallin are the kind of cruisers who make you want to drop everything and cast off the lines. Aboard SV Slacker, their 1986 Nauticat 33, they’ve been making their way around America’s Great Loop one marina, lock, and local gem at a time. Our team at Dockwa has been having the most wonderful time keeping up with their adventures and we 10/10 recommend giving them a follow over on IG for more cruising inspo. You can check out their page [here].
Today, they’re recapping their recent stopover in the Windy City. In their Chicago cruising guide below, you’ll find favorite local stops, marina recommendations, and the highlights that made their time in the city unforgettable.
Cruising Into the Heart of Chicago: A Boater’s Guide to The Windy City
By Haley and Josh Wallin of @CruisinCasa
We are Josh and Haley, currently doing America's Great Loop aboard our 1986 Nauticat 33 named Slacker. We left Stuart, Florida, on Valentine’s Day of this year and have made it 2,735 miles to Chicago, the Windy City!
Arriving in Chicago by boat is an experience everyone should have at least once in their life. Cruising down Lake Michigan and watching the skyline appear out of nowhere is magical. For so many miles of Lake Michigan, you see pristine beaches, huge sand dunes, and charming little coastal towns. So when the towering skyscrapers of the city come into view, it is a complete change of pace that feels absolutely welcome.
Once you enter through the breakwater, you are greeted with one of the best views anywhere in the city. Right in front of the Chicago Lock, the entire skyline stretches before you. When you finally snap back to reality after staring at the amazing architecture (more on this later), you quickly realize there are countless tour boats and water taxis crisscrossing in every direction.
We stayed at Navy Pier Marina, right in the heart of it all. Coming in through the main entrance of the harbor, you are greeted by Navy Pier front and center, and the marina is easy to find just on the north side of the pier. The dockhands were awesome, communicating exactly where our slip was, catching our lines, and providing all the arrival information we needed once we were tied up. The marina is geared toward transient boaters, with spotless bathrooms and showers, a brand-new washer and dryer, and an amazing boater’s lounge that was perfect for docktails. (There were many of those during our time there!)
Let’s talk about location. Navy Pier Marina is truly in the middle of it all. You can walk straight from your boat into the pier, and within three minutes you are surrounded by shops, restaurants, and bars, all of which offer exclusive discounts to marina guests. If you are lucky, there may even be a concert or two during your stay! In just 20 minutes, you can be at the Riverwalk enjoying a beer garden, winery, or restaurant along the Chicago River. It is also a great spot to host guests aboard during your stay in the city. My parents and sister joined us for a long weekend, and the amenities made it an absolute game changer.
There are about a million different things you can do in Chicago for a long weekend, but here are a few highlights we enjoyed. The architecture tour by boat was absolutely amazing and blew us away with the information and sights. For my father’s 60th birthday, we went to several great restaurants: The Purple Pig, Topo Gigio, Devil Dawgz, and Robert’s Pizza. All were fantastic, but there are countless other options. For drinks, London House has an incredible view of the Chicago River, the Palmer House Hotel is famous for its brownie old fashioned, and Northman Beer Garden was another favorite. My dad had one special request for his 60th: to visit the Redhead Piano Bar. When I say it was one of the best bars we’ve been to on the Loop, I am not exaggerating. The music was awesome, the drinks were solid, and the overall vibe was perfect. Of course, we also did the classic tourist stops: seeing the Bean, walking Michigan Avenue, and visiting Buckingham Fountain.
When it was time to wrap up our stay in Chicago and head down the rivers toward the Gulf, we had the incredible opportunity to take our boat straight through the city. This was easily the highlight of our visit. We left early, around 8 a.m., and as we slowly cruised down the river, we watched the city wake up, people rushing to work while we enjoyed a calm passage right through the heart of downtown.
Our time in Chicago was unforgettable, and if you are planning a trip by boat, Navy Pier Marina is a must. The location is unbeatable, the staff is excellent, and the amenities are top-notch.
To follow along on our journey, head over to Instagram @cruisincasa for real-time updates and whatever else we are getting into on a given day!
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