Chicago: Private Catamaran Sailing for up to 12 people

Chicago: Private Catamaran Sailing for Up to 12 People

Imagine gliding across the waters of Lake Michigan aboard Chicago’s largest chartered catamaran. For around $1,500, you and up to 12 friends or family can enjoy a private sailing adventure that lasts between 2 and 4 hours. Starting from Monroe Harbor, right in downtown Chicago, this experience promises spectacular skyline views, a touch of luxury, and plenty of opportunities for relaxation and fun.

What makes this trip stand out? First, the sheer space and comfort of the 38-foot catamaran, which feels more like a floating luxury apartment than a boat. Second, the ability to customize your cruise—whether you want to relax, party, or take a dip in the lake.

A couple of considerations: since you’re responsible for hiring your own qualified operator if your group exceeds six people, it adds a layer of planning. Also, while the boat has plenty of amenities—full kitchen, grill, floaties—drinks aren’t supplied, so you’ll want to bring your own or plan to BYOB.

This cruise suits travelers who crave a flexible, personalized day on the water, especially those celebrating special occasions or seeking a unique way to see Chicago from the lake.

You can check availability for your dates here:

Key Points

• Private luxury experience: Up to 12 guests can enjoy a tailor-made sailing adventure
• Flexible activities: Options for swimming, grilling, relaxing, or partying
• Stunning city views: Unbeatable perspectives of Chicago’s skyline and sunset
• Full amenities onboard: Kitchen, barbecues, floaties, Bluetooth sound system
• Cost efficiency: Great value for a private group in a luxury vessel
• Extra planning needed: Hiring a qualified operator if you’re not skippers yourself

Starting Point: Monroe Harbor and the Docking Experience

Your adventure begins at Monroe Harbor, located at the southeast corner of Monroe and LSD. It’s an ideal departure spot, right in the heart of downtown Chicago, with easy access to the city’s iconic skyline. A quick walk north of the Chicago Yacht Club puts you at the dock, where your boat awaits. Expect a friendly check-in with a yacht concierge who will help you settle in.

The location is perfect for combining your sailing trip with other city activities—no long commutes required. The boat is moored along the wall or at the dock, making access straightforward, especially if you’re staying downtown. An email confirmation with detailed directions will arrive 24 hours before your cruise, removing any last-minute guesswork.

The Vessel: Chicago’s Largest Chartered Catamaran

The 38-foot catamaran, named Latitude Adjustment, is designed with comfort and space in mind. It’s equivalent to a 70-foot monohull in terms of interior room, which means plenty of space to stretch out. The boat accommodates up to 13 guests, but most trips seem to comfortably host around 8-12 people.

Onboard amenities are impressive for a boat—full kitchen (with a stove and oven), large cooler, refrigerator, Bluetooth radio, and a barbecue grill. Floatie toys are available for water fun, making it easy to cool off with a swim if you choose. The vessel’s size and luxury features allow for a relaxed, intimate vibe, whether you’re celebrating a milestone, hosting a team event, or just taking a break from the hustle on a private cruise.

What to Expect During Your Cruise

Your cruise can be anything you want it to be—less about a scripted tour, more about your group’s interests. The owner emphasizes that it’s all about customization. You and your group can opt for a laid-back cruise, a lively party, or a combination of both. You might spend part of the trip sailing past the city skyline, then drop anchor for swimming and sunbathing.

If you decide to swim, you’ll love the floatie toys supplied, and the option to bring your own water toys or inflatables. The boat’s full kitchen and grill make for a great outdoor meal under the sky, with plenty of coolers and a fridge to keep your drinks cold. You are welcome to bring your own food and beverages, although alcohol isn’t provided.

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Setting Sail: From Sunset to City Lights

One of the most praised features is the ability to watch the sunset while sailing—a tranquil, reflective moment as the city’s lights begin to sparkle. Many reviews highlight the breathtaking views of the Chicago skyline, with its towering skyscrapers reflecting in the water. The boat’s open deck provides panoramic views, perfect for photos or just soaking it all in.

The captain or crew (if you hire one) will navigate out of Monroe Harbor, giving you a front-row seat to Chicago’s architectural marvels. The experience is flexible enough that you can focus on relaxing, enjoying a drink, or snapping photos of iconic sights like the Willis Tower, John Hancock, and Navy Pier.

The Experience: Fun, Relaxation, and Personal Touches

Unlike group tours that follow a set route, this private cruise adapts to your desires. If your group opts for a party cruise, the Bluetooth radio will keep the tunes flowing. If you’re celebrating a special occasion, the boat’s amenities make it feel like a floating private lounge.

You might find yourself drifting into quiet reflection as the sun dips below the horizon, or laughing with friends over a grilled meal. Many reviews mention the “unforgettable views” and the sense of freedom that comes from being on the water away from busy streets.

For those who want some adventure, water toys and swimming opportunities are available. Keep in mind, since drinks aren’t supplied, you’ll want to plan your BYOB carefully, especially if you’re celebrating something special.

The Practical Side: Costs, Planning, and Safety

The $1,500 fee covers your entire group for a 2-4 hour cruise, making it a solid value for a private experience. Of course, if you want a longer trip or additional amenities, costs could rise, but the base price is quite reasonable for a luxury private charter.

If your group exceeds six people, you’ll need to rent a qualified operator to skipper the boat. The owner provides a list of vetted professionals, with typical charges around $9-$11 per person per hour. This extra planning step is essential but manageable and ensures your safety and compliance with maritime laws.

While the boat is equipped for comfort and fun, you should bring your own drinks and food, as these are not included. The availability of coolers and a fridge makes it easy to keep your provisions chilled.

Who Is This Perfect For?

This cruise works best for small groups wanting a personalized, relaxed, and scenic outing. It’s ideal for celebrating birthdays, anniversaries, or just a day with friends. If you’re a family with kids who enjoy swimming, or a small team looking for a unique bonding experience, this boat ticks all the boxes.

Summary: Who Should Book This Experience?

If you value stunning skyline views, the flexibility of creating your own itinerary, and a comfortable, luxurious setting on Chicago’s waters, this private catamaran cruise is a winner. It’s particularly well-suited for those who want control over their schedule and enjoy waterside leisure—whether that’s swimming, grilling, or simply absorbing the city’s beauty from the lake.

The only caveats are the extra effort needed to hire a qualified operator if you’re not skipper-certified, and the need to bring your own beverages. But these small considerations are minor when weighed against the intimacy, comfort, and customization of this experience.

In essence, this cruise offers a rare chance to see Chicago from the water in style—a memorable outing for groups who want a little luxury combined with authentic lakefront views.

FAQ

Can I book this cruise for more than 13 people?
Yes, there are options for groups larger than 13. You’ll need to contact the provider directly for details and pricing.

What is included in the price?
The $1,500 fee covers the use of the vessel, a yacht concierge, cooler, refrigerator, full kitchen, Bluetooth radio, barbecue grill, floatie toys, and the ability to customize your cruise. Drinks and food are not supplied but can be brought along.

Do I need to hire a boat operator?
If your group exceeds six people and you do not want to skipper the boat yourself, you will need to hire a qualified operator. The owner provides a list of prescreened professionals.

How long does the cruise last?
Cruises can last anywhere from 2 to 4 hours, depending on your preference and availability.

Is swimming allowed?
Yes, swimming is an option if you want to cool off, with floatie toys provided for water fun.

What should I bring?
Bring your own drinks, food, and any water toys or inflatables you want to use. The boat has coolers and a fridge for your provisions.

Is there an age restriction?
People over 95 years old or prone to seasickness should consider their comfort level, as well as those over 331 lbs, for safety reasons.

What happens if I need to cancel?
You can cancel up to 24 hours in advance for a full refund. The booking is flexible, allowing you to reserve now and pay later.

Where is the meeting point?
Monroe Harbor, at the southeast corner of Monroe and LSD. A map and directions are sent 24 hours before your cruise.

Final Word

Booking a private sail on Chicago’s largest chartered catamaran offers a blend of luxury, flexibility, and breathtaking views. It’s an excellent way to celebrate, relax, and see one of America’s most beautiful skylines from a unique vantage point. Whether you’re planning a special occasion or just want to enjoy a day on Lake Michigan, this experience delivers a memorable, personalized outing that’s worth considering.

You can check availability for your dates here: