Chicago Sailboat Charters — Local services in Lake View Township

Updated review as of 9/30: the company contacted me after my original review below. They offered to extend my voucher to include a sail in late September when I could actually fly out to use it. I am editing my star rating from 2 to 4 for two reasons:

1. they did reach out to respond and accommodate me. Whether they did it on their own or as a result of my review here is unknown.
2. I REALLY had a great time sailing with the skipper who actually took us out and want the rating to reflect what a great experience it was despite the scheduling difficulties and rudeness of the staff replying to customer service emails. Ken was a fabulous captain and he will make sure you have a good time whatever that looks like for you. For me it was getting to helm the boat once we got out of the harbor! The other passengers on our sail didn't really care to steer or learn how to sail (which is also totally ok!) But they had a great time picnicking and drinking and catching up. Everyone had an excellent time and Ken made sure everyone was comfortable. I really enjoyed my conversation with Ken about his sailing experience and the weather patterns on lake Michigan. It turned out to be a really fun experience thanks to him and I'm glad I got the chance to revise my review. If you can get past the scheduling snafus you will likely have a fabulous time sailing with experienced skippers.

Original review: I bought a voucher through Groupon last year and was really looking forward to this sail. They cancelled due to weather (completely understandable!) and gave me an extension. problem was: 1) I live in Portland Oregon and 2) COVID hit. So I couldn't use it before it expired. I emailed the company to see if they could extend again and they replied back in July saying they could give it until 9/15. I went to start booking my trip including flights. Then discovered that they only had sails listed in August and beginning of September. I work at a hospital and my schedule is published 2 months in advance and we're especially tight now due to covid. I couldn't make the one date in September that they had available, so I wrote back again asking for help. Keep in mind I've already paid for this voucher last August 2019! So far they've been super unhelpful and uncaring. I was told I could pay another fee to extend my voucher again, and also told they don't have any other dates they can accommodate me this season. So I should just pay the extension free and HOPE they honor it later and have dates I can sail with them?? No thanks. I was super put off by how short and curt the emails are. They don't care about their customers in the least, no matter if you're from Chicago or across the country, or an essential hospital worker trying to catch a much needed break,...

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...

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...