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Page 9 of 10 • 240 listings
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Ashlee
Prestige Flybridge 59ft Luxury Yacht Charter in Chicago, Illinois
What an amazing experience! Armand has a beautiful boat with nearly every amenity you need. We had some slight changes with our schedule, but our captains, Matt & Craig every step of the way. Special shout out to Captain Matt! He was an amazing host, especially to our guests who weren't feeling well or who just needed to talk. The vibes were amazing, and everyone had a 10/10 time on the boat. Can't wait to hopefully book again this summer.
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Mark
Sailing Catamaran along Chicago's Lakefront 6ppl $450hr. Captain included.
Another Great Day on the Water This was my second trip with Captain Russell, and it won’t be my last. The boat is better than advertised — super clean and comfortable. Captain Russell just makes it easy. He knows what he’s doing, keeps everything relaxed, and makes you feel like you’ve got your own personal captain for the day. Always a great time out on the lake with him.
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Danielle
Sail & Swim from a Luxury Sailing Yacht
We had a great experience with Captain Greg. The boat was very nice and clean, and we had a great sunset sail! Our kids loved their first sailing experience. Captain Greg even taught my 9 year old how to steer and let all 3 kiddos help with hoisting the sails. Couldn’t have asked for a better night in Chicago!
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Christine
20 Passenger Captained Party & Event Boat in Chicago
We booked the boat for a work outing. It was such a fun way to celebrate and relax. Great skyline views, great Captains, who took care of us so well. The boat has everything you need.
MC
Mariah
26 ft. Chaparral SSX257 Luxury Vessel
We had an amazing time! The captain was super friendly, kept our safety a priority, and ensured we had fun. The boat was perfect for our group of 9!
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Sandra
Sailing Catamaran along Chicago's Lakefront 6ppl $450hr. Captain included.
Captain Russell was incredibly hospitable and entertaining, making this Afternoon Delight even more special. On the yacht was pure bless -- sunshine, bevies, great music and stunning Lake Michigan views. Plus there's a huge Yeti Tundra hard cooler onboard with ice... just bring your fav adult beverages. Highly recommend for a fun, luxe day with your besties.