Summer in Chicago means lots of boats on our big, beautiful lake and long, winding river. When I have company in from out of town, be it friends or family, we often head downtown so I can show off our awesome city on a boat tour. Here are the boat companies I’ve experienced and would highly recommend for exceptional service and an overall good time.

1. Shoreline Sightseeing. When possible I like to support family businesses – it may sound old school, but I just feel the service and attention is better. So my first choice when I want to explore our city by boat is Shoreline – they’ve been family owned for several generations and never disappoint. My first experience with Shoreline was an architecture tour several years ago. I’d been on a walking architecture tour before, but learning and seeing by boat was a fun new experience. Since then I’ve gone back for two more architecture tours, a bachelorette party wine tasting cruise, and a neighborhood brew cruise. Like I said, Shoreline never disappoints (and here’s a tip – if you visit their website you can save $5 on tickets).

2. Chicago’s First Lady. This is just a classy name for a boat business! This is my next choice because I consider myself a budding photographer, and Chicago’s First Lady is offering a new cruise – the Capture Chicago Photography Cruise. This cruise is for anyone who likes to take pictures, whether you’re using a smartphone camera or an expensive DSLR. A cruise full of photographers snapping unique shots of Chicago’s architecture is a fun way to spend 90 minutes (in my opinion). During the cruise the boat makes three scheduled stops for prime photo opportunities. Along the way crew members point out additional photo opps; you’re sure to head home with a whole album of original artwork.

3. Valara VI. If you enjoy theme parties, the Valara luxury yacht is sure to have a theme package that will make your next private party a huge hit. I had a blast at a Mardi Gras party aboard the Valara, (yes, quite a few strands of beads were exchanged). I’m considering hosting my own Wild West BBQ on board. Other theme parties include Island Adventure, Picnic on a Lake and Fun in the Sun. The Valara crew will make planning your party a snap – it will only look like you worked hard!

4. Spirit of Chicago. The famous Chicago Air & Water Show is coming up August 16-18, and if you’re like most people, you’ve watched it from the sand. Why not try something different this year, and watch it from the Spirit of Chicago? Spirit Cruises is offering several lunch, brunch and dinner cruises during the Air & Water show. Departing from Navy Pier, choose an afternoon cruise or end the day with a dinner cruise and fireworks. Either way, the Spirit of Chicago is a class act that will impress anyone.

5. Anita Dee Yacht Charters. Anita Dee is a lesser known gem that I highly recommend. Offering two private yachts that launch from Navy Pier, Anita Dee offers exceptional service and delicious food and beverages. I was on a client appreciation cruise for 100 on Anita Dee, and we all had a good time. Working with a smaller company can offer more choices and flexibility, and the staff at Anita Dee will work with you to meet your needs. In addition to private charters, Anita Dee has a regular sightseeing schedule available online for spur of the moment trips – wake up and want to hop on a boat? Head to the Anita Dee.


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