Chicago's Premier Yacht Fleet
Find Your Perfect Charter Experience
Alongside Chicago's most recognizable yachts, like Amalfi, Montauk and Sophisticated Lady, our 23-boat fleet is also well known for its cabin cruiser yachts, from 37 to 56 feet. A licensed captain handles the helm, so you can just enjoy the day.
BROWSE THE FLEET
The right boat for the day you're planning.
Coming March 2027 Burnham Harbor78' Amalfi
1 yacht in the fleet
Step aboard Amalfi, our 78' Power Catamaran—a commercial USCG Inspected yacht perfect for corporate events, weddings, and private parties. Inspired by sun-drenched Mediterranean elegance, Amalfi features a full service bar, premium bluetooth audio sound system, and multiple bathrooms—all managed by our professional captain and crew.
- Guests
- Up to 125
- Length
- 78 feet
- Bathrooms
- 2
- Harbor
- Burnham Harbor
- Full Service Bar
- Bluetooth Audio
- 2 Bathrooms
- Captain & Crew
$1,600/ hour
Captain & crew included. Bar packages, tax and service charges additional.
Burnham Harbor72' Sophisticated Lady
1 yacht in the fleet
The Sophisticated Lady, a 72' Chris Craft moored out of Burnham Harbor, is a commercial USCG Inspected yacht that accommodates up to 49 passengers. Perfect for corporate events and large reception boat parties, this yacht includes 3 floors, 2 bathrooms, a full service bar, and premium bluetooth audio sound system.
- Guests
- Up to 49
- Length
- 72 feet
- Bathrooms
- 2
- Harbor
- Burnham Harbor
- Full Service Bar
- Bluetooth Audio
- 3 Floors
- 2 Bathrooms
$1,350/ hour
Captain & crew included. Bar packages, tax and service charges additional.
River North Marina57' Montauk
3 yachts in the fleet
Set sail in style aboard our newest vessel, Montauk. This luxurious power catamaran, inspired by the timeless charm of the Hamptons, comfortably accommodates up to 49 passengers. Featuring a sleek design with coastal decor, the boat reflects Montauk's relaxed elegance. Enjoy top-tier amenities including a full service bar, catering options, a full JL Audio surround sound system, and a private bathroom—all managed by our professional crew. Whether you're planning a private event or a scenic tour, Montauk delivers an unforgettable experience on the water.
- Guests
- Up to 49
- Length
- 57 feet
- Bathrooms
- 1
- Harbor
- River North Marina
- Full Service Bar
- Bluetooth Audio
- 1 Bathroom
- Captain & Crew
$1,000/ hour
Captain & crew included. Bar packages, tax and service charges additional.
Planning something for work? See our Chicago corporate boat charter packages for team outings, client events, and company parties.
Planning food for your charter? See our yacht catering menus and bar packages, delivered to the dock and served aboard.
31st Street Harbor56' Sea Ray Sundancer
2 yachts in the fleet
Excellent for entertaining, this stylish sport coupe yacht features an oversized U-shaped seating area equipped with a custom dual PA and DC Bluetooth Audio. Below deck, the yacht features a cherry wood-finished saloon, well equipped galley, wet bar, two staterooms, and two full bathrooms.
- Guests
- Up to 13
- Length
- 56 feet
- Bathrooms
- 2
- Harbor
- 31st Street Harbor
- Kitchen
- Wet Bar
- Fuel
- Bluetooth Audio
$420/ hour
Captain fees additional. Under USCG bareboat regulations, the vessel is chartered without crew and you select and pay your captain directly. During checkout, choose from our list of approved licensed captains, averaging $100–$125/hr.
31st Street Harbor52' Sea Ray Sundancer
1 yacht in the fleet
Step aboard the Sea Ray 460 Sundancer, a spacious and comfortable yacht designed for an unforgettable day on the water. For a boat in this size range, the 460 offers an excellent layout for entertaining, with a roomy cockpit, comfortable seating, and plenty of space for guests to relax, socialize, and enjoy the views.
- Guests
- Up to 13
- Length
- 52 feet
- Bathrooms
- 2
- Harbor
- 31st Street Harbor
- Kitchen
- Wet Bar
- Fuel
- Bluetooth Audio
$395/ hour
Captain fees additional. Under USCG bareboat regulations, the vessel is chartered without crew and you select and pay your captain directly. During checkout, choose from our list of approved licensed captains, averaging $100–$125/hr.
31st Street Harbor50' Sea Ray Sundancer
3 yachts in the fleet
Meet the Sea Ray 450 Sundancer, a sleek, well-appointed cruiser built for easy days on Lake Michigan. The 450 pairs a wide-open cockpit and generous bow seating with plenty of room for your group to spread out, soak up the sun, and take in the skyline.
- Guests
- Up to 13
- Length
- 50 feet
- Bathrooms
- 2
- Harbor
- 31st Street Harbor
- Kitchen
- Wet Bar
- Fuel
- Bluetooth Audio
$350/ hour
Captain fees additional. Under USCG bareboat regulations, the vessel is chartered without crew and you select and pay your captain directly. During checkout, choose from our list of approved licensed captains, averaging $100–$125/hr.
31st Street Harbor48' Sea Ray Sundancer
4 yachts in the fleet
Equipped with one of Sea Ray's widest beams, this yacht is most popular for its large open cockpit and cabin floorplan, making it phenomenal for social events, birthdays, and bachelorette parties.
- Guests
- Up to 13
- Length
- 48 feet
- Bathrooms
- 1
- Harbor
- 31st Street Harbor
- Kitchen
- Wet Bar
- Fuel
- Bluetooth Audio
$335/ hour
Captain fees additional. Under USCG bareboat regulations, the vessel is chartered without crew and you select and pay your captain directly. During checkout, choose from our list of approved licensed captains, averaging $100–$125/hr.
31st Street Harbor46' Sea Ray Express
4 yachts in the fleet
Equipped with an upgraded JL Audio Bluetooth Audio, starboard facing U-shaped seating area, and full sized cabin with bathroom. This express style cruiser is great for both family outings and entertaining.
- Guests
- Up to 13
- Length
- 46 feet
- Bathrooms
- 1
- Harbor
- 31st Street Harbor
- Kitchen
- Wet Bar
- Fuel
- Bluetooth Audio
$310/ hour
Captain fees additional. Under USCG bareboat regulations, the vessel is chartered without crew and you select and pay your captain directly. During checkout, choose from our list of approved licensed captains, averaging $100–$125/hr.
31st Street Harbor37' Sea Ray Sundancer
4 yachts in the fleet
The 37ft Sea Ray Sundancer is ideal for small groups seeking a sleek, intimate day on the water. Featuring an upgraded JL Audio Bluetooth sound system, a comfortable cockpit, and a cozy cabin with one stateroom, one bathroom, and a convenient kitchenette, it’s the perfect compact cruiser for relaxed lakefront adventures.
- Guests
- Up to 13
- Length
- 37 feet
- Bathrooms
- 1
- Harbor
- 31st Street Harbor
- Kitchen
- Wet Bar
- Fuel
- Bluetooth Audio
$285/ hour
Captain fees additional. Under USCG bareboat regulations, the vessel is chartered without crew and you select and pay your captain directly. During checkout, choose from our list of approved licensed captains, averaging $100–$125/hr.
Choosing the boat is just
the beginning.
Skyline cruises, Playpen afternoons, fireworks after dark.
Where will your day take you?