Chicago Sailboat Charters

"We had our charter with Chicago Sailboat Charters Company and it will seriously be a day my friends and I’ll never forget. Had lots of fun as the captain knew what he was doing and had good knowledge of the area and the best spots. Loved sailing with them."

"This review is based on the actual sailing experience, and condition of the boat, which was listed as large class 36'. Last year I made a reservation for a morning sail using the Travelzoo voucher, which was a good discount from the regular rates. This was a party of six, not counting the captain. The morning was cool and a bit overcast but not calling for rain. We powered out of the harbor into the lake and the captain said we'll sail with just the jib today. That was okay but made for a slow sailing experience. My friend said this boat was very similar to the one our friend bought in Seattle, and we went below in the cabin to look around and compare. The cabin was not in the best of shape, it looked like an old camper with antiquated equipment and tired beat-up finishes. It definitely wasn't a place you'd want to spend time in unless you had too. But we were there for the topside sailing experience, not interior condition. The sail was slow and gentle, somewhat boring aside from learning about; and seeing where, the Chicago freshwater intake pipes were located. The captain was a nice young man though and overall it was a different and pleasant way to start the day. Afterwards I realized that I should have tipped the captain more; based on the full price, so I apologize for that."

"O.k. Full disclosure, we did not use Chicago Sailboat Charters. However, we were out sailing our own boat and Captain Bill and first mate Nancy sailed up next to us on a beautiful Sunday afternoon. We exchanged some pleasantries, talked for a bit, and I asked if they would so kind as to take some photos of our boat and send them to me. 20 years of sailing in Chicago and no one has ever been so kind as to take pictures *and* actually share them with me. Ms. Nancy sent me 15 some photos and I was positively thrilled. In our brief conversation, and subsequent emails I learned that Captain Bill and Ms. Nancy are live-aboard cruisers in the Caribbean during the off-season (heck, that's 2 stars right there) aboard an IP 44 (another 2 stars ;-) ). We'll add a final star for the photos they sent. Clearly, these are competent sailors, which you can't always ensure when chartering out of Chicago. There are plenty of folks running charters who aren't even licensed, insured, and/or helm'd by competent captains, let alone competent sailors. No doubt the day will be great when you get out on the lake, and you really should get out there and enjoy Chicago from the water. My only regret is my lack of consideration, and not returning the favor of taking pictures for them, reciprocating the favor. My own excitement got the best of me, but I'll be on the lookout for Chicago Sailboat Charters in the future and make sure I try and grab a photo or two for them."

"We just had the best experience with Captain Bill on our sailboat cruise!! It was a beautiful day, and Bill made the whole experience even more enjoyable. He was knowledgable, easygoing and provided us with a safe and relaxing sail along Lake Michigan. He even allowed us to steer the boat. We brought snacks and drinks and were able to sit on the bow of the boat to soak in the sun and scenery. It was a perfect day!"

"We took a group of 10 out with Captain Rob and First Mate Allison and the service and experience were phenomenal. We had two families with kids ranging from 12 to 21 and everyone had a great time. We did a fireworks charter on Wednesday evening off Navy Pier and the views were fantastic. Safety was paramount with the kids and the crew did a great job making this a really enjoyable experience. Thanks Captain Rob!!! We will be back and request you every time."