SO MUCH FUN!! How it…read moreworks: You charter a boat along with the captain and crew. The boats are owned by the company. We chartered a boat on Labor Day, with Bill and Nancy. We departed from Montrose Beach. We were able to bring our own drinks and snacks for the sail. There were 7 of us total at ~$100/person. We specifically selected this company because they had a money back guarantee in the event of inclement weather - most other boating companies do not offer this! HUGE PLUS. Fun Fact: All of their boats mean "Lost" in different language, but not to be confused with lost at sea!

We had an excellent charter experience with Captain Bill on a speedboat. Booking the boat was quite…read moreeasy through the website, then you can contact the captain yourself to see who is available (company gives names/contact info). I would definitely rent from CSC again. Prices were also pretty average compared to other companies! Definitely recommend.

Great experience, easy departure, fast, transparent communication We had an amazing time.read more

We rented this yard for a birthday and had amazing time. We are especially like the sound system.read more

Captain Tim is the best and so is his beautiful, clean boat! He can help create the perfect vibes…read morefor your party with all the accommodations needed to have a great time. This is the only charter I recommend to people!

if you are looking for a wonderful experience on the water in Chicago, this is the boat tour to…read moretake! Captain Tim is very accommodating and his boat tours are always a blast! I highly recommend if you are looking for someone on time, fun and entertaining and most importantly a great tour! Dor Sea Tours should be your top pick!

Included everything to make sure everything was perfect and easy going. All the girls from the…read morebachelorette party wish to go back! Thank you for making everything enjoyable for everyone!

Booked Captain Tom's Penalty Box for my boyfriend's Birthday! Sent out information on Tom's website…read moreand Tom got back at me the next day. Whenever I have questions I'll just text Tom and he usually replies pretty quick. We scheduled the cruise at 3 but we didn't get to the harbor until almost 4 due to traffic. Tom is very understanding. We brought some food and drinks and Tom has a cooler with ice ready on the boat. Started off with a Chicago river cruise. My boyfriend got a bit sea sick when we were cruising on the lake... what can I say, freaking Chicago wind, but the river cruise is calm and nice. Caption Tom is patient to explain all the functions of the boat (wow two engines) and other interesting facts about Michigan Lake and Chicago river. We got caught in the rain for a bit but lucky the boat has a roof and we brought cards. When we got back on the lake the sun came out again so we stayed a while for a little lake front swim party... kinda funny since my boyfriend can't swim. Tom eventually find a rope to tie to his life vest so he had fun. Finished off the cruise at around 8 as we planed. Great day! Highly recommended!

Went here for a sunset sail with my boyfriend. Really…read moreEnjoyed being able to go on a sail boat. They let volunteers from the crowd pull open the sails. Staff is friendly and funny.

Windy City Sailing always exceeds expectations. My family and I look forward to our annual sailing…read moretrip w/ Captain Joe and his crew. Even just unplugging on a three hour tour beats some week long vacations we've taken in terms of the chill factor. Our family and friends pretty much compete every year to be the lucky ones who get invited to join us. Our favorite one is the Air & Water Show. Can't wait for this year's trip.

Had the most incredible experience on seabird sailing! Eric is an amazing captain and makes…read moreeveryone comfortable, the boat was stunning, and the views were immaculate. We came for an engagement shoot but will be back every summer!

I could not recommend Seabord Sailing enough. I chartered a private trip with them to propose to my…read morenow fiancé and it was a phenomenal experience - I would trust them to celebrate any event. They prioritize safety and are amazing hosts. If you're going to sail Lake Michigan, sail with this outfit, they're incredible.

They cancelled and won't give my money back. Lost $1000. They should be ashamed of themselves, how…read moreis this legal??

We had a blast! Gorgeous yacht and awesome crew. Spending memorial day on Stray Kat was amazing…read moreexperience. We absolutely loved everything.