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On A Boat Sailing

Luxury Sailing Adventures Along Chicago's Lakefront

📍Navy Pier Marina - Downtown Chicago

All bookings protected by our "Golden Sail" Money-Back Guarantee

What makes On A Boat Sailing different?

If you appreciate attention to detail, hospitality, and luxury amenities, this is the group booking for you! Our Chicago sailboat charters & cruises have been enjoyed by thousands of guests since we started in 2018. As we hit the waterfront for our 8th season, we pride ourselves on offering an unforgettable way to experience Lake Michigan from the City.

25+ years of sailing experience means smooth sailing for guests.

Captain Greg Scannell and First Mate Cait Scannell are world-class sailors. Their resumé includes an 8-month, 5,500 nautical mile voyage from Chicago to the Bahamas and back in 2021. They share their passion for sailing and affinity for Lake Michigan with guests every year.

Enjoy VIP amenities aboard our french-built, 37' sailing yacht, S/V Dragonfly.

Dragonfly offers the flexibility of adventurous sailing with the option to drop anchor & swim or float on The Lake. Passenger amenities include full access to upper and lower cabin seating, ample fridge space, and a private bathroom.

We're still perfecting the art of luxury sailing experiences in Chicago. Let us show you!

This isn't like other boat rentals. Our custom charters go above and beyond to provide luxury and comfort for your group. On top of world-class sailing

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700+ PRIVATE SAILING CHARTERS SINCE 2018

Trusted superhost to thousands of guests, each & every year.

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Check out our luxury sailing experiences with this reel:

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BYOB. Luxury Amenities. Captain Included. starting at $899

Lock in your preferred date & time with a 50% fully-refundable deposit. Availability is limited.

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This 4-hour, all-inclusive group sailing adventure is our best seller for birthdays and bach parties! Enjoy world-class sailing paired with a private swim & float party aboard our 37' luxury sailboat, Dragonfly.

Bookings include:

 

🥂  Complimentary Champagne Toast

🥜  Unlimited Snacks & Non-Alcoholic Beverages

🍻  BYOB + Fully-Stocked Ice, Beers & Seltzers

🦩  Access to All Floaties & Rafts

🛎️  Fresh Towel Service for All Guests

 Starting at $1,199
Up to 7 Guests

FRI • SAT • SUN
Departing 10am & 2:30pm

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Looking to Sail & Swim with more than 7 guests?

Check out Sailing Chi's Sail & Swim+ for more time on a larger boat with a bigger group of your friends!

​This 3-hour, all-inclusive sail & sip cruise begins with sunset sailing along Chicago's famous skyline, with optional night swimming and concludes with a VIP viewing of the famous Navy Pier fireworks show.

 

Bookings include:
 

🥂  Complimentary Champagne Toast

🥜  Unlimited Snacks & Non-Alcoholic Beverages

🍻  BYOB + Fully-Stocked Ice, Beers & Seltzers

Starting at $899
Up to 7 guests

WEDNESDAY'S 6:30pm SATURDAY'S 7:30pm

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Real reviews from actual guests:

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This 3-hour private sailboat cruise will take you & your guests on a favorable sail down the gorgeous coastline of Chicago's lakeshore, all aboard our 37' luxury sailboat, Dragonfly. Expect: 

🌆  Clear views of Chicago's iconic architecture
⛵  The waterfront experience
in style, comfort & class

📸  Unlimited snapshots to get the perfect summer profile pic

Starting at $899
Up to 7 guests

WED • FRI • SUN
Departing 3pm & 6:30pm

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​This 2-1/2 hour private sailing cruise promises breathtaking views of our nightly summer sunset aboard Dragonfly. Enjoy the sights & sounds of Lake Michigan at sundown, including:​​
 

🌇 Unbelievable views of Chicago's historic skyline
📷 Incredible lighting to get the perfect summer pic

🌅 Golden hour like you've never seen before

Starting at $899
Up to 7 guests

FRIDAY'S & SUNDAY'S
Departing 6:30pm

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Three easy steps to pre-book your private boat party for summer 2025:

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STEP 1 - Choose Your Adventure
Browse our all charters & cruises page to choose the experience that suits you.

STEP 2 - Recruit Your Crew
Fire up those group chats and start recruiting. S
ummer weekends will sell out.

STEP 3 - Lock-In Your Big Day
Book with a 50% fully-refundable deposit. Remaining balance to be auto-debited 5 days ahead of reservation.

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Golden Sail Money-Back Guarantee

Bad weather? Unexpected issues? We recognize things come up. Our money-back guarantee ensures you have the freedom to make adjustments with ease, providing peace of mind in the weeks and days leading up to your planned outing with us.

100% Refund up to Two Weeks From Departure

50% Refund up to 48 Hours From Departure

Full Refund for Weather Related Cancellations

Swap Dates With No Fees
Subject to Availability

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Our Chicago sailing experiences are filling up.
Don't get left in the wake - Book now!

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