On A Boat Sailing

On A Boat Sailing ⛵️ Private Sailboat Charters & Cruises
📍 Navy Pier Marina - Chicago, IL
👨‍✈️ USCG-certified Cpt.

Greg Scannell
👥 Accommodates up to 7 guests
🌇 Celebrate birthdays, bach parties, engagements, proposals, reunions, family outings and more! We're a one boat, one captain business sharing our passion for sailing from the docks of Monroe Harbor in Downtown Chicago. 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.

Summer is half way over or just half way getting started?! Get us on the calendar now, your winter self will thank us la...
08/01/2025

Summer is half way over or just half way getting started?! Get us on the calendar now, your winter self will thank us later

Happiest of days on a boat sailing! 📸
07/31/2025

Happiest of days on a boat sailing!
📸

Summer vibes off to a hot start ☀️😎🌆📸 radziszewski eats.chi
06/26/2025

Summer vibes off to a hot start ☀️😎🌆

📸 radziszewski eats.chi

500 five star reviews and accounting! Thank you for all the positive feedback over the years ⛵️💛🌆
06/17/2025

500 five star reviews and accounting! Thank you for all the positive feedback over the years ⛵️💛🌆

“Nikolina, will you marry me?” 📸
06/05/2025

“Nikolina, will you marry me?”

📸

Some of our favorites from 2024, can’t wait to see what 2025 brings! Reserve your date now for an exclusive sailing phot...
05/05/2025

Some of our favorites from 2024, can’t wait to see what 2025 brings! Reserve your date now for an exclusive sailing photoshoot. Link in bio.
📸
📸

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

Alerts

Be the first to know and let us send you an email when On A Boat Sailing posts news and promotions. Your email address will not be used for any other purpose, and you can unsubscribe at any time.

Contact The Business

Send a message to On A Boat Sailing:

Shortcuts

Featured

Share

Category