SailTime Chicago

07/02/2026

Rick W has a boat in our Waukegan, IL fleet. But, he wanted to catch the fireworks at Navy Pier last night. Should he sail his own boat down, 5 hours each way?

Nope, Rick took advantage of our SailTime Plus program and booked a Beneteau 38.1 in Burnham Harbor! For a few hundred dollars, he and his guests had a completely new sailing experience at a marina he'd never been to before.

SailTime Plus is available to all our members, giving them access to boats across our network from Chicago to Sydney Australia.

06/14/2026

There are still a few more hours of the boat show left! Come on down to Burnham Harbor and check it all out!

A three-day event featuring more than 100 in-water boats and yachts is taking place in Chicago this weekend.

06/13/2026

Thanks to everybody who has made this event at the Windy City Boat & Yacht Show a sailing success!

06/03/2026

Have you signed up for the Start Sailing Now experience at the Windy City Boat & Yacht Show yet? Space is filling for fun!

06/02/2026

The Windy City Boat & Yacht Show is featuring a program just for never-ever sailors that we are doing called Start Sailing Now!
Sign up today to reserve your spot! link in the comments

05/28/2026

Start Sailing Now! At the Windy City Boat & Yacht Show Space is extremely limited and the sign up link is in the comments!

Most people say they've always wanted to try sailing.
Most people never do.
This is your excuse.
Sign up now 👉 Link in comments
June 12-14 | Burnham Harbor | $89 | Spots limited at the Windy City Boat & Yacht Show with SailTime Chicago ⛵

05/19/2026

Want to take a 3 hour sail with a SailTime captain and 5 of your best friends out of Waukegan Harbor? Of course you do, that sounds like a really fun day. Nice wind, glass of wine or 2, plenty of sunshine and laughs.

But what if I told you that this fun day of sailing also benefitted local co-op AAUW Preschool that could use the support? Well, now your fun day with friends is also uplifting our community.

So please, bid on a fun day of sailing at the link below. And know your fun times will be giving support to kids that need it in Waukegan.

Relax on the waves of Lake Michigan on a 3-hour sail with up to six (6) of your closest friends! Board a SailTime luxury sailboat out of Waukegan Harb

05/06/2026

Rest in Peace to Sailing Hall of Famer Ted Turner.

Back in 1970 Ted sailed in the Race to Mackinac, and beforehand scoffed at Lake Michigan, calling it a "mill pond". Days later he was fighting 60knot winds and massive seas that forced 88 boats out of the race. During the storm he announced to his crew mates that he publicly renounced any aspersions he cast on inland lake sailing.

Hell of a sailor, that guy.

04/10/2026

We got the Eye of Tiger today, 4 boats floating already and we're working through lunch to launch as many as we can before quitting time.

03/24/2026

If you know anyone looking to have a sailing adventure this Spring, our buddies at SailTime Boston Boat Club and First Reef Sailing School are sailing their boats from the USVI back to Boston. And you can join them as crew!

Locally, our Spring deliveries are about 35 miles. They have 2 non-stop legs of 650 and 850 miles to cover!

The goal of First Reef Sailing’s mile-building passages is to provide our students the first hand experience of sailing a multi-day offshore passage as we deliver our training boats from our summer location in Boston, MA to our winter location in the US Virgin Islands and back. This provides an o...