top of page

Search


Sailing the Caribbean Begins!
The Joy of Sailing Carib is about to begin cruising the Windward Islands. That is Grenada to Martinique. There is a dedicated website for information about what we do and when. www.thejoyofsailingcarib.org We have so much fun in the Chicago summers...let's keep it going! The action starts mid January and ends in early June. We sail out of four major islands and take in others when we can - Grenada, St. Vincent/Grenadines/Bequia, St. Lucia and Martinique. Check out the website

Captain Lynda
Nov 211 min read
End of Season Bookings
Ahoy sailors! As the season winds down we are getting very few bookings and it's coming in as one sailor per session which as you know...

Captain Lynda
Oct 11 min read


Last Sail of the Season Oct. 18
There's room for six sailors to join for the 5-6 hour sail up to Waukegan where Leela will sleep for winter. Come join us for an...

Captain Lynda
Oct 11 min read



Captain Lynda
Sep 230 min read


Air and water Sailing Sat and Sun
There are two spots left on both Saturday and Sunday come join us bring snacks. We start at 11 and finish at three. We will swim if the...

Captain Lynda
Aug 131 min read
Let's Make Waves for the Great Lakes!
We’re hitting the water and racing with purpose! Our crew has come together not just to sail fast—but to make a real impact for the Great...

Captain Lynda
Aug 121 min read



Captain Lynda
Jul 310 min read


Save the Date: Sunday 12/15/24 Launch Party for The Joy Of Sailing the Caribbean! 3-6 pm
Yes it’s finally here! We have purchased a Bavaria 39 Cruiser for fun times in the Spanish Virgin Islands as well as the US and British...

Captain Lynda
Nov 26, 20241 min read


Game Night & celebrating Nicole Tonight!
7 pm Chicago Corinthian Yacht Club. Help us cheer for Nicole’s bday. The galley and the bar will be open for food and drink. We will of...

Captain Lynda
Oct 5, 20241 min read


Long distance opportunity! Chicago - Waukegan - Racine October 12 and 13, 2024
Ok, so things always get a little back n forth when deciding when to take the boat North. As of right now the weather is looking good...

Captain Lynda
Oct 1, 20241 min read


End of Season Schedule 2024
Join us for the last few sails of the season! Sign up online today or call Lynda for a last minute add. Wed Oct 2 - 6 pm Pleasure Thu Oct...

Captain Lynda
Oct 1, 20241 min read
Mid Day Sail Thursday 1 pm
Lets grab some sunshine and sail early on Thursday. It’s noted as a pleasure sail, but those who want to can work the boat. The season...

Captain Lynda
Sep 30, 20241 min read
Parade Postponed!
Mermaids and Pirates Parade will now be Sunday Sept. 8 at 1 pm

Captain Lynda
Sep 1, 20241 min read
4th of July Weekend!
Ahoy Joy of Sailing website and sailing members! We have plans for a great holiday weekend including a full day of floatin' and boatin'....

Captain Lynda
Jul 2, 20241 min read
Leela Delivery Sat/Sun
It has been a real trial, trying to find the right weather window to bring Leela down from Racine. After many reschedules it now looks...

Captain Lynda
May 5, 20241 min read


Black Friday Sale Helly Hansen Vests
Ahoy! The Helly vests are on sale at Amazon! Was $125 is now $93.75 We will be printing them with Joy of Sailing so grab yours and then...

Captain Lynda
Nov 21, 20231 min read
Save the date! Nov. 16. @ 7pm
All sailors from the season 2023 are invited to My Home for our end of year gathering and the first book club planning meeting! More...

Captain Lynda
Nov 3, 20231 min read


Sat Oct 21/22. Still room!
Weather has pushed us to one week later. As of right now, weather looks like our favorite west wind at 10 to 15 kn which is perfect! 60...

Captain Lynda
Oct 16, 20231 min read


Rainy Day Game Day! Saturday 10/14 @ 1 pm
We sailors need to make cheery as the season end presses on us and the weather prohibits us. With our sail to Waukegan and Racine now...

Captain Lynda
Oct 13, 20231 min read


Fall return trip postponed! Now Sat Oct 21/22
Weather has pushed us to one week later. As of right now, weather looks like our favorite west wind at 10 to 15 kn which is perfect! 60...

Captain Lynda
Oct 10, 20231 min read
bottom of page
