Imagine waking up to the gentle sway of a sailboat on crystal-clear Caribbean waters, surrounded by lush islands, vibrant cultures, and endless opportunities for adventure. The Joy of Sailing Carib 2027 is ready to make that dream your reality. After a highly successful season with over 10 groups exploring the stunning Caribbean, we are excited to announce our sailing schedule for 2027 — now featuring new destinations like Grenada, St. Lucia, Martinique, and Dominica. To secu

Friday 2-6 pm at Leela. B dock slip 55. Get sparkly! You’ll love it!!!

The Joy of Sailing Carib Gals at SVG Race Week! The Joy of Sailing Carib continues to be an awesome program with women joining and Sailing throughout St. Vincent and Grenadines. Just wanted to send an update to help you motivate for the beginning of The Joy of Sailing in Chicago season 2026. Our Sailing vessel Life Aquatic will be brought back to Trinidad and hauled out on June 5. After six days, I will return to Chicago and begin preparing Sailing vessel Leela! Looks like th

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

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...

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...

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...