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Dorchester Center, MA 02124
Experience Chicago’s skyline on a private 38' luxury catamaran with amenities, swimming, and sunset views—ideal for groups seeking a memorable water adventure.
Chicago: Private Catamaran Sailing for up to 12 people — A Complete Review
Sailing across Lake Michigan on a private catamaran offers a one-of-a-kind way to see Chicago from a fresh perspective. This experience, hosted by 3rd Coast Cruising, promises a luxurious, customizable outing suited for groups of up to 12 people, whether celebrating a special event, team-building, or simply craving an escape on the water. The vessel is Chicago’s largest chartered catamaran, equipped with all the bells and whistles to turn a day on the lake into a memorable adventure.
What immediately catches the eye is the stunning skyline views and the overall sense of comfort and exclusivity. We love that this trip isn’t just about sightseeing — it’s about creating moments, whether through a relaxing sail, a swim, or a lively barbecue. The only potential drawback? The cost might seem steep for some, but considering the size, amenities, and flexibility, it offers excellent value for a private, personalized experience.
This tour is best suited for groups who want an intimate, high-end experience that combines relaxation, fun, and unbeatable scenery. If you’re planning a special celebration or simply want a unique way to explore Chicago from the water, this private catamaran ticks all the boxes.
Setting the Scene: Departure from Monroe Harbor
Your adventure begins at Monroe Harbor, situated on the southeast corner of Monroe and LSD, conveniently close to downtown Chicago. As you walk north of the Chicago Yacht Club, you’ll find the dock where your vessel, Latitude Adjustment, awaits. The owner or a designated captain will conduct a safety briefing before setting sail, ensuring everyone is well-informed and comfortable.
The departure point’s location is perfect for those staying in or visiting downtown Chicago, providing easy access without long transit times. The email reminder 24 hours prior offers helpful directions, so arriving on time is straightforward.
The Vessel: Chicago’s Largest Chartered Catamaran
The boat itself is a sight to behold — a 38-foot luxury catamaran, which, in terms of space, feels more like a 70-foot monohull. The generous layout means your group has plenty of room to spread out and enjoy the ride. The vessel features a full kitchen with a stove and oven, a barbecue grill, a Bluetooth radio for tunes, and a large Yeti cooler and refrigerator for drinks and snacks.
What Sets This Apart: The Amenities and Customization
Guests frequently mention how well-equipped the boat is — from floaty toys for water fun to a full kitchen for preparing grilled meals. The flexibility to bring your own food and drinks (BYOB) adds a personal touch, letting you tailor the experience to your tastes. Whether it’s a casual chill-out cruise, a lively party, or a combination of both, this vessel adapts to your mood.
The Itinerary: Highlights and Flexibility
Spectacular Views and Photo Opportunities
Guests consistently mention the breathtaking views of the Chicago skyline, especially during sunset. Watching the city light up as the sun dips below the horizon creates a peaceful, reflective atmosphere. For those who love photography, this cruise offers plenty of chances to capture stunning vistas framed by the city’s towering buildings.
Water Activities and Relaxation
If your group wants to cool off, the boat’s floaty toys and proximity to Lake Michigan make swimming an appealing option. While drinks are not supplied, the cooler and refrigerator make it easy to keep beverages chilled. Many reviewers note that the vessel’s comfort and amenities made the experience feel more like a floating luxury lounge than a standard boat trip.
The Crew: Attentive and Flexible
The yacht concierge and crew members are praised for their attentive service and flexibility. They’re there to cater to your needs, whether that’s helping with grilling or providing water toys. If you prefer not to operate the boat yourself, you’ll need to hire a qualified operator, which is a legal requirement. The owner provides a list of vetted operators, with costs estimated around $10-$11 per person per hour, plus gratuity.
Pricing: An Investment in Experience
At $1,500 for up to 13 guests, this experience offers significant value for a private, luxury outing. When you consider the amenities, the exclusivity, and the stunning views, it’s a compelling option for groups wanting more than just a boat rental — it’s a tailored adventure. The price includes taxes, cleaning, and fuel, making it a transparent deal.
Duration and Flexibility
Available from 2 to 4 hours depending on your booking and preference, you can choose a shorter sunset cruise or a longer daytime trip. The flexibility to reserve now and pay later adds to the convenience, especially if your plans are still taking shape.
Sailing fans have several other Chicago options to choose from
If you’re seeking a high-end, private water adventure in Chicago, this cruise is hard to beat. It’s perfect for celebrations like birthdays, anniversaries, or bachelor/bachelorette parties, as well as corporate team-building or client outings. The ability to customize the trip makes it suitable for laid-back relaxation or lively parties.
However, remember that it’s not suitable for those prone to seasickness, over 331 lbs, or with mobility issues, given the boat’s specifications and safety regulations. Also, if you’re not comfortable skippers or hiring a captain, you’ll need to budget extra for operator services.
This private catamaran experience combines luxury, stunning scenery, and flexibility to create a memorable day on Lake Michigan. The focus on customization means you can craft an outing that suits your mood perfectly, whether that’s a relaxing cruise, a water-based celebration, or a lively party. The vessel’s amenities, like the full kitchen, barbecue, and floaty toys, elevate the experience from ordinary to extraordinary.
While the cost may seem high compared to standard boat rides, the exclusivity, size, and comfort justify the price for those seeking a premium outing. It’s an ideal choice for groups wanting privacy, flexibility, and a chance to see Chicago from a unique vantage point.
For those who value the stunning skyline views, personalized service, and a luxurious setting, this cruise offers a fantastic way to enjoy Chicago’s lakeside charm.
Is this experience suitable for large groups?
Yes, the boat can host up to 13 people comfortably, making it perfect for small groups or celebrations.
Can I bring my own food and drinks?
Absolutely. You can BYOB and bring food to grill on board. The boat has a full kitchen, refrigerator, and cooler to keep everything fresh.
How long does the cruise last?
The duration ranges from 2 to 4 hours, depending on your booking. Check availability for specific starting times.
Do I need to hire a captain or operator?
If your group exceeds six people and you choose to bareboat, you’ll need a qualified operator, which costs approximately $9-$11 per person per hour. The owner provides a list of vetted operators.
What should I wear?
Casual, comfortable clothing suitable for being on the water. Bring layers if you plan to stay until sunset, as it can get cooler.
Is this experience child-friendly?
Most reviews don’t specify age restrictions, but given the water-based nature and safety requirements, it’s best suited for older children and adults.
What about seasickness?
The tour is not suitable for those prone to seasickness. If unsure, consider taking precautions beforehand.
To sum it up, this private Chicago catamaran cruise offers a blend of luxury, adventure, and unparalleled views that are perfect for making special memories. Whether you’re celebrating or just wanting a unique way to see the city, it’s a splurge worth considering for your next Chicago trip.
More ways to experience Chicago from the water include these boat tours