top of page


Ian Malanes
Aug 14, 20242 min read
7 Must-Know Tips for First-Time Sailors with Windy City Sailing
Starting out on your sailing voyage can bring a mix of excitement and a touch of nervousness. At Windy City Sailing we aim to ensure you...

Ian Malanes
Aug 7, 20242 min read
A Yacht Tour Can Elevate Your Wedding Anniversary Celebration
Celebrating your wedding anniversary is an occasion that deserves an unforgettable experience. Picture commemorating this milestone on...

Ian Malanes
Jul 23, 20242 min read
Why Choose Windy City Sailing for Your Private Yacht Charter Experience?
Looking for a top-notch luxury yacht charter in Chicago? Look no further than Windy City Sailing! Whether you're seeking an escape...

Ian Malanes
Jul 15, 20242 min read
The Ultimate Chicago Air Show Viewing Party on a Yacht
Experience the magic of observing the Chicago Air Show from the setting of a yacht! Say goodbye to the crowded beaches. Come aboard for...

Ian Malanes
Jul 5, 20242 min read
2024 Summer Guide to Chicago
Welcome to the summer guide for 2024 in Chicago also known as the Windy City! There are plenty of events amazing attractions and endless...


Ian Malanes
Jul 5, 20242 min read
Why Sailing is Great for Your Mind and Relaxation Needs
In today's paced world it's crucial to find ways to unwind and take care of your well-being. Sailing offers a blend of peace, excitement,...


Ian Malanes
Jun 29, 20242 min read
Planning to Celebrate 4th of July on the Water; Windy City Sailings Special Charter Experience
The 4th of July is a time to come together show patriotism and create lasting memories, with loved ones. This year elevate your...

Ian Malanes
Jun 14, 20242 min read
Plan Your Perfect Special Event with Windy City Sailing: Birthdays, Anniversaries, and More
Picture yourself marking a moment surrounded by the views of Chicago's skyline and the calm waters of Lake Michigan. Whether it's a...

Ian Malanes
Jun 7, 20242 min read
Lake Michigan's Hidden Gems: Explore with Windy City Sailing
Lake Michigan, known as the gem of the Midwest is more than a body of water with picturesque views. Along its shoreline lie hidden...

Ian Malanes
Jun 6, 20242 min read
Welcome To Sailing Season: Experience Lake Michigan like Never Before with Windy City Sailing
Welcome to the sailing season on Lake Michigan! With the arrival of weather and calm waters now is the time to immerse yourself in the...

Ian Malanes
May 31, 20242 min read
How to Create Memorable Moments with a Navy Pier Firework Charter
When it comes to creating memories there are things that can compare to a Navy Pier Firework Cruise with Windy City Sailing. Imagine...

Ian Malanes
May 27, 20242 min read
Corporate Retreats and Teambuilding on Lake Michigan
Organizational getaways and team-building exercises are crucial, for promoting collaboration lifting spirits, and improving efficiency....

Ian Malanes
May 24, 20242 min read
Summer Evenings in Chicago: Enjoying the Navy Pier Fireworks Show aboard a Yacht
When it comes to summertime in Chicago there's nothing like the excitement and beauty of watching the Navy Pier fireworks display from...

Ian Malanes
May 14, 20242 min read
How Long Is a Yacht Season? When to Charter in Chicago
When thinking about renting a yacht in Chicago timing plays a role. Chicago's yachting season provides views of the city skyline and...

Ian Malanes
May 8, 20242 min read
Make Father's Day Extraordinary with Chicago Bareboat Charter
Father's Day is here. What a perfect way to celebrate with a special sailing trip on Lake Michigan! Treat your dad to an experience with...


Windy City Sailing
Jun 14, 20236 min read
Insider’s Guide to Chicago Summer 2023 Activities
Chicago is a city that comes alive during the summer months, with plenty of exciting things to do and see. As a local, I have explored...


Windy City Sailing
Jun 7, 20233 min read
Experience the thrill of Sail Grand Prix at Navy Pier – Chicago in 2023
Calling all sailing enthusiasts! Get ready to witness some of the world’s best sailors compete at the upcoming Rolex United States Sail...


Windy City Sailing
May 22, 20233 min read
Catch the Perfect Sunset on Chicago Sailing Trips
For the perfect summer evening activity, why not take a sailboat out onto the water and watch the sun slowly set over the stunning...


Windy City Sailing
May 1, 20236 min read
Discover the Best Things to Do in the Windy City during Summer
Are you looking for something to do in the Windy City this summer? Look no further than Chicago’s countless attractions, events, and...


Windy City Sailing
Apr 24, 20232 min read
Boating Safety Tips
Boating is a fun and relaxing way to enjoy the water. However, it also comes with some risks and responsibilities you should know before...
bottom of page