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Page 2 of 9 • 211 listings
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carolynn
Sail & Swim from a Luxury Sailing Yacht
This is an iconic trip in Chicago. I have always been on the river walk or on a kayak looking at people boats and thought "Those lucky kids." So this time I rented a sailboat to go out on the lake- even luckier! The operators are very organized and helpful. Everything was as expected from the site. Communication throughout was excellent. Thanks for lovely and memorable sail. I'm coming back to jump in the lake when the water temperature is a bit warmer :)
RJ
Rachel
50' Multi-level Luxury Yacht with Party up to 12
Captain Jim and his team went above and beyond to make our charter an unforgettable experience. From the moment we departed to the smooth arrival back at the dock, everything was handled with professionalism, confidence, and a warm, friendly attitude. The boat was immaculate, the ride was smooth, and Captain Jim clearly knew the waters like the back of their hand. They made us feel safe, relaxed, and completely taken care of the entire time. Whether it was pointing out interesting sights, adjusting course for the best views, or making sure we had everything we needed on board, their attention to detail was exceptional. You can tell they truly love what they do—and it shows in the way they connect with guests and manage every aspect of the trip seamlessly. I highly recommend Captain Jim and his team, to anyone looking for a top-tier charter experience. Thank you again for an incredible day on the water!
MA
Mahab
46' Spacious Portofino Party Yacht in Chicago For Every Occasion
Had the best time out on the water with Captain Kyle! He was super professional, friendly, and made sure we felt comfortable and had fun the entire trip. The boat was clean, spacious, and had everything we needed. Kyle knew all the best spots and kept the vibe fun and relaxed. You can tell he really knows what he’s doing and loves what he does. Highly recommend booking with him — can’t wait to go out again!
RS
Robert
Double Decker 50ft Sea Ray Flybridge Yacht!
This motor yacht is a great boat for the Oak St. playpen. We had a terrific time and luckily the weather cooperated! The boat is in great condition and offers multiple lounging areas. The speaker system connected easily and allowed us to listen to all our favorites. Using the backend on the stern we were able to also lounge halfway in the water with some beach chairs. Looking forward to the next time we boat with "Liquid Asset"!
Ari
39' Sea Ray Sundancer - Motor Yacht for Charter in Chicago, Illinois
Captain James and Captain John were wonderful hosts. They were clear about procedures and safety that made my group feel really comfortable. The boat was clean and ready for our use. We had a great time at the playpen. I’d definitely book again if in the Chicago area. Thank you again!
Lynnae
Captained Charter on 60ft Martini Sea Ray Luxury Motor Yacht in Chicago
Great service great crew great experience! Michael was a very helpful and very nice deckhand! Captain Natalia was very experienced informative and thorough making sure we all made it back safe. Can’t stop hearing “3 points of contact!” in my head lol love it! Will be booking again soon.