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Meet the 2023 Rio Sport Coupe 44, one of the most unique charter yachts ever to arrive in Chicago. Built in Italy, the Rio 44 is not a typical cruiser. It is a modern sport coupe with a completely different feeling from the usual Chicago charter boat. The magic is the layout: the aft deck, cockpit, galley, helm, lounge, and salon all flow together into one open social space. When the sliding glass door disappears to the side, the boat feels like one continuous indoor-outdoor lounge floating through the skyline. This is the boat for guests who want something rare, elegant, and conversation-starting. The teak cockpit is spacious and flat, with a large sofa, two tables, sun lounger, outdoor kitchen, refrigerator, microwave, and a concealable TV. The helm area has a sliding glass roof, side window, and long side glazing that fills the space with air, light, and panoramic views. Below deck, the Rio offers a luxury two-stateroom, two-head layout with separate showers, giving it the comfort and privacy of a much larger yacht. Powered by twin CAT 7.1L diesel engines with joystick control, bow and stern thrusters, hydraulic platform, and sunroof, this 44-footer brings Italian performance, comfort, and style into one unforgettable Chicago charter experience. This is not just another boat listing. This is a first-of-its-kind Chicago yacht experience.


Why Book Me I love what I do with a passion that shows I have a knack for reading a group and adjusting for the vibe. I offer free sea sick patches that often save the day. I take a keepsake photo & print one out for everyone on charter for free - always a hit. I bring my own Insta360 for some great photo videos for your group for free! Just learning to fly my drone - happy to capture some unique videos. I bring plenty of portable phone batteries - so you are never untethered! I am arguably the most 5 star reviewed captain in Chicago - read the reviews. When I'm not driving, I'll juggle, clean up around you and refresh your drinks. I bring my own awesome floating saddles for fun in the water. I know the best fireworks locations in the harbor. I navigate the Chicago locks to get you in and out of the river.
You’ll get helpful information for your departure after your booking is confirmed.
Street Address For Arrival
Departure Location
Free cancellation up to 7 days before your trip.
Weather Policy: If it is unsafe to operate on the day of your charter due to weather, then we will give you a full refund or reschedule at a discounted rate on a date/time the boat is available. On the day of your charter, we have the authority to deem whether weather conditions are considered safe or unsafe. Uncharterable weather conditions are typically the result of (but are not limited to) heavy storms, waves forecasted over 4+ feet, small craft advisory warnings, gale storms, and strong winds. Light rain and passing storms are typically considered safe. In the case that conditions are considered unsafe, our team will work with the guests to temporarily postpone or reschedule your charter to a future date. RENTAL AGREEMENT: A boat rental agreement will be sent by email, following the booking confirmation, for your review and signature. This agreement must be signed for the rental to proceed. WAIVERS: Our insurance company requires that all passengers sign a liability waiver. This waiver must be signed by all passengers prior to the boat's departure from the dock. Please note - hourly pricing varies between weekdays, weekends and holidays. Pricing noted is for regular weekend rates.