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 12 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 flying by! This is how you get out of the group chat and on a boat while it’s still here!!! ⚓️ ⛵️
07/14/2026

Summer is flying by! This is how you get out of the group chat and on a boat while it’s still here!!! ⚓️ ⛵️

On Wednesday, June 24th, 2026, we had the honor of organizing an informal regatta for the Equilar Summit 2026 in Chicago...
06/27/2026

On Wednesday, June 24th, 2026, we had the honor of organizing an informal regatta for the Equilar Summit 2026 in Chicago. Twenty-six sailors learned the basics of sailing, raced on Lake Michigan and got to enjoy a raft up picnic lunch at Ohio Street Beach. Not the weather we had hoped, but it was all smiles! Big thank you to Morgan Stanley for sponsoring the event and Navy Pier Marina for hosting. Photos by Mega Snaps Inc thank you Sailing Chicago and Nijole Z Adler for captaining as well. “I am not afraid of storms, for I am learning how to sail my ship.” — Louisa May Alcott

Need weekend plans? Look no further! We are wide open and Summer-Time-Chi is officially here! We are giving 20% off all ...
06/23/2026

Need weekend plans? Look no further! We are wide open and Summer-Time-Chi is officially here! We are giving 20% off all bookings plus a free premium drink package (valued at $200) for any Sail & Swim booking

05/06/2026

Who’s ready for summertime chi and nights like these?

04/20/2026

PSA: sunset cruises make for the perfect date 😉🧡🌇

Navy Pier Fireworks return Memorial Day Weekend and continue every Wednesday and Saturday evening through Labor Day! Our...
04/10/2026

Navy Pier Fireworks return Memorial Day Weekend and continue every Wednesday and Saturday evening through Labor Day! Our location offers the best possible location for boating to and from the show.

03/27/2026

The best way to catch a sunset in Chicago is On A Boat Sailing!

Counting down the days until we’re back on the docks
03/07/2026

Counting down the days until we’re back on the docks

Exumas, Bahamas February 2026 with our two best crew!
02/28/2026

Exumas, Bahamas February 2026 with our two best crew!

Address

Chicago, IL
60605

Telephone

+13126197858

Website

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