On A Boat Sailing

On A Boat Sailing We're a one boat, one captain business sharing our passion for sailing from the docks of Monroe Harbor in Downtown Chicago.

⛵️ Private Sailboat Charters & Cruises
📍 Chicago, IL
👨‍✈️ Captain Greg & 1st Mate Cait
👥 Up to 10 Guests
🌇 Chicago Lakefront Cruises, Skyline Sunset Cruises, Sail & Swim Playpen Charters, Navy Pier Fireworks Cruises
www.onaboatsailing.com Our trips have been enjoyed by thousands of guests since our first private charter in 2017. We pride ourselves on offering a safe & unforgettable experience on Lake Michigan for you & your group.

It’s been another epic year of sailing. Thank you for incredible memories and new experiences. We hope your upcoming yea...
12/31/2024

It’s been another epic year of sailing. Thank you for incredible memories and new experiences. We hope your upcoming year is full of sailing. With us!

Anyone else remember when you had to post one photo at a time on Instagram so you picked the raddest one?📸
08/29/2024

Anyone else remember when you had to post one photo at a time on Instagram so you picked the raddest one?

📸

Raise a glass if you’re ready for the first weekend of summer 🙋‍♀️🥂⛵️ 📸 💃 .andrews
06/21/2024

Raise a glass if you’re ready for the first weekend of summer 🙋‍♀️🥂⛵️

📸
💃 .andrews

We are avid sailors and enjoy sharing our passion for sailing with travelers and locals! For us, sailing offers adventur...
05/22/2024

We are avid sailors and enjoy sharing our passion for sailing with travelers and locals! For us, sailing offers adventure, relaxation, and the discovery of new places and people. Greg holds a Master Captain’s license from the US Coast Guard, and Cait is a professional architect. Together we have sailed the Great American Loop, Bahamas and Caribbean.

Cait first bought Dragonfly in 2016 after having taken lessons from Greg earlier that summer. Greg said, “I hope you kno...
05/22/2024

Cait first bought Dragonfly in 2016 after having taken lessons from Greg earlier that summer. Greg said, “I hope you know boats are a lot of work.” Cait thought to herself, “I need a guy who likes to work on boats.” The rest is history, but little did the two of us know that in 2018 we’d start a sailing charter together on Dragonfly. Eight years later, over 600 private charters, a great loop trip and countless memories it’s needless to say the boat is a part of the family.

03/30/2024

Sometimes we sail into a dreamscape. Come sail away with us into cotton candy skies.

Address

Chicago Yacht Club 400 E Monroe Street
Chicago, IL
60605

Telephone

+13126197858

Website

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Our 2025 Schedule is live and the Black Friday/Small Business Saturday Sale is now on! Book with code “BlackFriday” and receive $300 off!!

Sometimes we sail into a dreamscape. Come sail away with us into cotton candy skies.

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