Chicago: Private Catamaran Sailing for up to 12 people

If you’re dreaming of seeing Chicago from a fresh angle, a private sailing trip could be just the ticket. While I haven’t personally taken this exact tour, I’ve looked into what it offers—and it sounds like a pretty special way to enjoy the Windy City’s skyline, especially if you’re looking for privacy and a touch of luxury.

What really caught my eye? First, the largest chartered catamaran in Chicago—that’s a lot of space for your crew. Second, the customizable experience, from lounging and swimming to grilling and partying, makes it appealing whether you’re celebrating or just craving a relaxing day on the water.

Of course, there’s a potential caveat: this experience requires you to skipper the vessel yourself if your group is over six people, which might not appeal to everyone. Still, if you’re comfortable with a bit of hands-on sailing or are open to hiring a qualified operator, this could be a memorable getaway. This tour works well for groups who want privacy, great views, and a flexible itinerary.

Key Points

• Largest Charter Catamaran in Chicago offers spacious comfort and versatility.
• Customizable options include lessons, tours, chill-out, parties, and swimming.
• Includes luxury amenities like full kitchen, grill, floaty toys, and Bluetooth sound system.
• Ideal for private groups of up to 12 (13 with special arrangements), perfect for celebrations.
• Requires a skipper if your group has more than six people; you’ll need to hire a qualified operator.
• Breathtaking city views and sunset sailing create memorable moments.

You can check availability for your dates here:

What You Can Expect from This Sailing Experience

This private catamaran adventure starts from Monroe Harbor, nestled in the heart of downtown Chicago. The boat itself is a 38-foot luxury sailing vessel, which, despite its modest size, feels surprisingly spacious—equivalent to a 70-foot monohull, according to the provider. With room for up to 12 guests comfortably, it’s a solid choice for groups seeking privacy without sacrificing space.

The Vessel and Amenities

The Latitude Adjustment catamaran is well-equipped. You’ll find a full kitchen with a stove and oven, which is perfect if you want to prepare a meal or snacks onboard. There’s also a barbecue grill—great for a casual cookout as you sail. For keeping drinks cool, a large Yeti cooler and refrigerator are at your disposal, but drinks themselves are not provided, so bringing your own BYOB is encouraged if you want to loosen up with some beverages.

Onboard entertainment comes from a Bluetooth radio—ideal for setting your playlist—and plenty of floaty toys to keep everyone entertained during swimming breaks. The trip options are flexible—whether you want a lesson, a tour, to chill out, or party cruise mode, the experience can be tailored to your mood.

The Route and Views

Sailing from Monroe Harbor, your route maximizes views of Chicago’s iconic skyline, including the Willis Tower, John Hancock Center, and Navy Pier. The experience promises breathtaking scenery, especially during sunset, which creates a peaceful, almost magical atmosphere. This isn’t just about the sights; it’s about experiencing the city from a different perspective, feeling the wind, and enjoying a slower pace.

Water Activities and Swimming

If you’re craving some water fun, the boat has floaty toys available for swimming and lounging. While the tour doesn’t specify stops at particular swimming spots, the option to anchor and take a dip is available—adding another layer of enjoyment to the trip.

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The Practicalities of Booking

The price is $1,500 per group, accommodating up to 13 people, which breaks down to about $115 per person for a two-hour cruise—less if you extend it to four hours. Given the size of the vessel and the amenities, this seems like good value, especially for a private, customizable experience.

One crucial point: if your group has more than six people, you’ll need to hire a qualified operator to skipper the boat for you. The provider offers a list of vetted professionals, with additional costs estimated around $9 to $11 per person per hour. Be prepared for this extra expense if you want to relax completely and let someone else handle the sailing.

Meeting Point and Logistics

Meet at Monroe Harbor, located on the southeast corner of Monroe and Lake Shore Drive (LSD). The provider sends a reminder email with directions 24 hours before your trip, making it straightforward to find the boat. The process is simple, and the private nature of the cruise means you won’t be sharing the space with strangers.

Duration and Flexibility

Trips range from 2 to 4 hours, depending on your booking. The shorter options are perfect for a quick escape, while a longer cruise offers more time for swimming, relaxing, and enjoying the views. You can reserve now and pay later, giving you the flexibility to plan your trip without upfront commitments.

Who Is This Experience Best Suited For?

This sailing adventure is ideal for groups seeking privacy and flexibility—be it for celebrations, small parties, or simply a different way to see Chicago. It’s perfect if you want a luxurious, customizable experience, and don’t mind paying a bit extra for the amenities and exclusivity.

However, it may not be the best choice for those prone to seasickness, or travelers who prefer a more structured, fully guided tour. If you’re comfortable with a bit of sailing and are willing to hire an operator if needed, this experience could be a highlight of your trip.

The Bottom Line

For anyone looking to enjoy stunning views of Chicago’s skyline from the water, this private catamaran cruise offers a blend of comfort, customization, and exclusivity. The spacious vessel and amenities promise a relaxed day whether you’re celebrating, bonding with friends, or just craving a change of scenery.

The flexibility to bring your own food and drinks, combined with options to swim and party, makes it a versatile choice for many types of trips. A bit of extra planning is required if your group is larger than six, but that’s a small price for the privacy and tailored experience on offer.

If your idea of a memorable day includes good company, stunning city vistas, and a touch of luxury, this sailing trip could be a perfect fit. Just remember to consider your comfort with sailing and hiring an operator, and you’ll be set for a wonderful adventure on Chicago’s waters.

FAQs

Is this a guided tour?
The experience includes a live English tour guide if you opt for a tour or lesson, but if you’re over six guests, you’ll need to hire a qualified skipper separately. The provider supplies a list of vetted operators.

Can I bring my own drinks?
Yes, drinks are not provided, but you’re welcome to bring your own BYOB. The boat has coolers and a refrigerator for your convenience.

What’s the maximum group size?
The maximum is 13 people with special arrangements. The standard capacity for the vessel is 12, but larger groups can inquire about options.

How long is the cruise?
Cruises typically last 2 to 4 hours, depending on what you book. Shorter trips are great if you want a quick escape, while longer ones give more time for activities.

What should I wear?
Casual, comfortable clothing is best. Bring layers if you plan to sail during cooler months or evenings, and don’t forget sunglasses and sunscreen.

Is it suitable for children?
The tour is primarily designed for adults and private groups; there’s no specific mention of children’s suitability. Consider your group’s comfort with sailing.

Do I need to worry about seasickness?
If you’re prone to seasickness, it’s worth noting that this is an open-water sailing experience, and some rocking can occur. If you or any guests are particularly sensitive, take precautions.

What happens if I need to cancel?
You can cancel up to 24 hours in advance for a full refund, which offers some flexibility if your plans change.

If you’re thinking about a unique way to see Chicago and love the idea of a private boat experience, this sailing trip ticks a lot of boxes. Just keep in mind the extra considerations about skipper arrangements and bringing your own drinks, and you’re likely to have a day that’s truly unforgettable.

You can check availability for your dates here: