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We will go as far as wind takes us, with no destination, but never loose sight of beautiful Chicago skyline.

Sunsets are so beautiful and almost never the same.

Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois

With Captain

5.0(336 reviews) ·

610 bookings

the United States,Illinois,Chicago,Sailing

Unavailable
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Relaxed, scenic sails on Lake Michigan with a calm, welcoming vibe, mixing peaceful cruising, city views, swimming, sunsets, and even fireworks outings.

Comfortable classic sailing vessel that cruisers praise for smooth, quiet rides, easy lounging on deck, and a pleasant setup for photos, swimming, and city viewing.

Guests highlight exceptionally clear communication, flexible timing, skilled, safety‑minded captains, and a warm, confident presence that helps everyone feel at ease.

Renters say this listing is great for:

Family TimeDate NightsSunset CruisingPhotography

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AI Overview

Owner's Description

ABOUT THE TRIP: Experience the beauty of Chicago from the water aboard our private 36' C & C Cruising Monohull, “Harmony.” Whether you're celebrating a special occasion or simply enjoying a day on the lake, this sailing adventure is perfect for up to 6 people. Cruise the waters and take in the stunning views of the Chicago skyline, enjoy the tranquility of the lake, and create unforgettable memories with friends and loved ones. This private charter is ideal for birthdays, anniversaries, engagements, photo shoots, or just a relaxing get-together. Set sail during the day to soak up the sun or in the evening for a breathtaking view of the city lights. On Wednesday and Saturday nights, enjoy the spectacular fireworks show from Navy Pier right from the comfort of the boat—no crowds, just a perfect view! ABOUT THE BOAT: “Harmony” is a 36’ C & C racing/cruising monohull, designed for comfort and performance. This sleek and well-maintained vessel offers ample space for up to 6 passengers, ensuring a relaxing and smooth ride on the water. WHAT'S INCLUDED: - A private, luxurious sailing experience for up to 6 guests - Captain to guide your journey - Stunning views of Chicago’s skyline and waterfront - A relaxing and comfortable sail on a well-maintained 36' monohull WHAT'S NOT INCLUDED: - Tips for the captain (always appreciated, but not mandatory) - Food and beverages (available for you to bring along) DEPARTURE LOCATION: Depart from the beautiful Chicago shoreline for your unforgettable adventure on the water. OTHER THINGS TO KNOW: - Minimum booking of 2 hours - Fireworks shows on Wednesday and Saturday nights for an added treat - Food and drinks are welcome to be brought along for your charter

Nijole

610 total bookings

Superowner

Best of 2026

Capacity: 6 guests

Sailing: Cruising Monohull

Reviews

5.0 (336 reviews)

Listing Accuracy
Awesome
Departure & Return
Awesome
Vessel & Equipment
Awesome
Communication
Awesome
Value
Awesome
Itinerary & Experience
Awesome

244 photos have been added by reviewers who booked this listing.

MJ
Meneka

Sailing with Nijole and her husband was an incredible experience! From the start, they were very responsive in communication and flexible with our requested times, even allowing us to extend once on the water. Their knowledge, warmth, and passion for sailing made the trip both safe and fun, with stunning views that we’ll never forget. Highly recommend!
SB
Sean

Excellent experience all around. Our excursion was a great mix of swimming and peaceful cruising under sail. Nijole was a great captain and created a wonderful experience for a family afternoon on the water.
ZD
Zinnia

Amazing experience with top-notch communication from start to finish. Super responsive and incredibly knowledgeable—especially helpful for first-timers in Chicago. They guided us around the lake and to the perfect fireworks viewing spot, even capturing great photos for us. The captain was skilled and professional, and the music made the ride even better. Highly recommend!
KM
Kasey

I booked this experience because Nijole had amazing reviews — and now I truly know why. She is talented, no-nonsense host who knows exactly how to make you feel comfortable when you're aboard. We could not have been more grateful or had a better time. Thank you, Nijole! A superstar.
Alexander

Such a great outing! We went for my girlfriend’s birthday and had the best time. Amazing boat, amazing captain, amazing dog! Could not have gone better.