Chicago: Private Catamaran Sailing for up to 12 People

Imagine gliding across the tranquil waters of Lake Michigan, with the iconic Chicago skyline as your backdrop. This private catamaran sailing adventure offers a unique way to experience the city’s breathtaking beauty. From the spacious 70-foot vessel, you and up to 11 of your closest friends can soak in the sun, grill up a delicious feast, and create unforgettable memories. The luxury and convenience of this excursion are sure to leave you captivated, but the true highlight might just be the opportunity to unwind and surrender to the serene surroundings.

This experience made our article of 3 Top-Rated Chicago Sailing Experiences.

Key Points

• Enjoy a private catamaran sailing experience in Chicago starting at $1,500 for groups of up to 12 people, with a cruise duration of 2 to 4 hours.
• Spacious catamaran equipped with a full kitchen, grill, floaty toys, large cooler, and refrigerator, offering comfort and amenities for an unforgettable sailing adventure.
• Experienced crew available for hire to handle navigation and boat handling, allowing guests to relax and focus on the breathtaking views of the Chicago skyline and sunset.
• Free cancellation option up to 24 hours in advance with no upfront payment required, making the booking process flexible.
• Catamaran not suitable for individuals prone to seasickness, over 331 lbs (150 kg), or over 95 years old, ensuring a safe and enjoyable experience.

You can check availability for your dates here:

Overview and Pricing

With private catamaran sailing in Chicago, visitors can experience the city’s stunning skyline from the water.

Starting at $1,500 per group, this 2-4 hour cruise allows up to 12 people to sail on the largest chartered catamaran in Chicago.

Fully equipped with a kitchen, grill, toys, and refrigerator, the luxurious amenities ensure a comfortable journey. Guests can relax, swim, and enjoy the breathtaking views, with the option to hire a qualified operator if desired.

Plus, free cancellation up to 24 hours in advance and no upfront payment make booking the experience hassle-free.

Vessel Details and Capacity

Sailing on Chicago’s largest chartered catamaran, equivalent to a 70-foot monohull, guests can experience the city’s waterways in style.

This 13-person vessel comes equipped with a full kitchen, grill, floaty toys, a large cooler, and a refrigerator for all your onboard needs.

Bluetooth radio provides entertainment, while the luxurious amenities ensure a comfortable sailing adventure.

Whether you’re looking to swim, grill, or simply relax and take in the breathtaking views of the Chicago skyline and sunset, this catamaran offers the perfect platform for your group’s private excursion.

Amenities and Experience

Luxurious amenities await guests aboard this private catamaran, ensuring a comfortable and memorable sailing experience.

The vessel boasts:

A full kitchen, grill, and refrigerator, allowing groups to indulge in delectable meals and refreshments while taking in the stunning skyline and sunset.

1. A full kitchen, grill, and refrigerator, allowing groups to indulge in delectable meals and refreshments while taking in the stunning Chicago skyline and sunset.

2. Floaty toys, perfect for cooling off with a refreshing swim during the warm summer months.

3. A Bluetooth radio, setting the mood with your favorite tunes as you relax and unwind on the open waters.

The yacht concierge is on hand to cater to your group’s every need, creating an unforgettable private sailing adventure.

Operator Requirements

For groups over six, the vessel must be rented, and guests can either operate it themselves or hire a qualified operator.

Hiring an experienced crew costs approximately $10 – $11 per person per hour, in addition to the rental fee. A list of prescreened operators is available for verification, ensuring a safe and enjoyable sailing experience.

The operator will handle navigation, boat handling, and cater to the group’s needs, allowing guests to sit back, relax, and enjoy the breathtaking views of the Chicago skyline and sunset.

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Important Information and Restrictions

The meeting point for this private catamaran sailing experience is at the S/E corner of Monroe and Lake Shore Drive in Monroe Harbor.

To ensure a safe and enjoyable voyage, there are a few important restrictions to keep in mind:

1. Not suitable for individuals prone to seasickness, over 331 lbs (150 kg), or over 95 years old.

2. A reminder email will be sent 24 hours prior to the cruise with detailed directions.

3. Guests can expect breathtaking views of the Chicago skyline and sunset, along with opportunities for swimming, grilling, and relaxation during the 2-4 hour sail.

Booking and Reservation

To secure your private catamaran sailing experience in Chicago, guests can reserve their booking easily online.

The reservation process is straightforward, allowing you to select your preferred date, time, and group size. Once your booking is confirmed, you’ll receive a reservation confirmation via email, and there’s no need for any upfront payment.

Simply pay later to finalize your reservation. With a flexible cancellation policy, you can make changes or cancel your booking up to 24 hours in advance for a full refund.

Finalize your reservation with a flexible cancellation policy, allowing changes or cancellations up to 24 hours in advance for a full refund.

Securing your Chicago catamaran sailing has never been easier.

Group Size and Customization

Accommodating groups of all sizes, the Chicago catamaran sets sail with a generous 13-person capacity.

For larger parties, additional options are available, ensuring a customized experience tailored to your needs.

The vessel’s spacious layout and thoughtful amenities create an ideal setting for:

1. Corporate outings and team-building activities

2. Celebratory events like birthdays, anniversaries, or bachelor/bachelorette parties

3. Intimate gatherings of family and friends seeking a unique and memorable outing on the waters of Lake Michigan.

Whether you’re planning a small intimate gathering or a larger celebration, the Chicago catamaran has the flexibility to accommodate your group’s size and preferences.

Getting to the Sailing Location

Reaching the sailing location is a breeze, as the departure point at Monroe Harbor, situated at the S/E corner of Monroe and Lake Shore Drive, offers ample parking nearby. The location is easily accessible by public transportation, with the closest CTA stations being Millennium Station and Monroe Station. For a truly seamless experience, the operator will send a reminder email 24 hours prior to the cruise with detailed directions to ensure a smooth arrival.

| Getting to the Sailing Location |

| — | — | — | — |

| Parking | Public Transportation | Reminder Email |

| Ample parking available near Monroe Harbor | Closest CTA stations: Millennium Station and Monroe Station | Sent 24 hours prior to the cruise with directions |

The Sum Up

Sail away on a luxurious catamaran in the heart of Chicago, taking in the city’s stunning skyline and vibrant atmosphere. This private cruise offers unparalleled relaxation, with ample amenities and the convenience of a dedicated yacht concierge. Whether you’re looking to entertain guests or simply enjoy a serene escape, this sailing adventure promises an unforgettable experience on the waters of Lake Michigan.

You can check availability for your dates here: