A Step-by-Step Guide to Your First Sailboat Charter with Windy City Sailing

Ian Malanes
Apr 22
3 min read

There’s nothing quite like gliding across the sparkling waters of Lake Michigan aboard a sailboat, especially when you’re sharing the experience with friends, family, or colleagues. Don't let the idea intimidate you if you’ve never chartered a sailboat.

At Windy City Sailing, we specialize in making your first sailboat charter smooth, stress-free, and unforgettable. In this step-by-step guide, we’ll walk you through everything you need to know to plan the perfect group outing.

Step 1: Decide on the Purpose of Your Outing

Before diving into the details, consider why you plan this sailboat charter. The purpose will help shape the rest of your decisions:

Corporate Team-Building: Looking to strengthen workplace bonds? Sailing encourages teamwork and communication.
Celebrations: Birthdays, anniversaries, or bachelorette parties—Lake Michigan provides a stunning backdrop for any milestone.
Family Reunions: Bring everyone together for quality time away from screens and distractions.
Relaxation: Simply want to unwind? A leisurely sail is perfect for reconnecting with nature and each other.

Once you’ve defined your goal, it’ll be easier to customize the experience.

Step 2: Pick the Perfect Date and Time

Timing is everything when planning a memorable sailboat outing:

Seasonal Considerations: Late spring through early fall offers the warmest weather and calmest waters.
Day vs. Night Sails: Daytime sails are great for sightseeing, while sunset or evening cruises add a touch of magic.
Weekdays vs. Weekends: Weekday charters are often less crowded and may come with better availability.

Pro Tip: Book early to secure your preferred date, especially during peak seasons like summer weekends.

Step 3: Customize Your Experience

One of the perks of chartering with Windy City Sailing is the ability to tailor every aspect of your trip:

Activities Onboard: To enhance the experience, add extras like sailing lessons, team-building exercises, or even live music.
Catering Options: From light snacks to full gourmet meals, we partner with local caterers to meet your culinary desires.
Themed Events: Want to host a “Roaring Twenties” party or a nautical-themed soirée? Let us know, and we’ll help bring your vision to life.

Customization ensures your outing feels personal and unique.

Step 4: Prepare Your Group

Make sure everyone knows what to expect and how to prepare:

What to Wear: Comfortable clothing and non-slip shoes are recommended. Don’t forget sunscreen, sunglasses, and a hat!
Safety Briefing: Our certified captains will provide a quick safety overview before departure. It’s easy to follow and ensures peace of mind.
Special Requests: Inform us beforehand if anyone in your group has dietary restrictions, mobility concerns, or other special needs.

Step 5: Relax and Enjoy the Ride

Once you’re onboard, let go of any worries and immerse yourself in the beauty of Lake Michigan. Whether you’re steering the boat, snapping photos of the Chicago skyline, or simply lounging with a drink, the experience promises to be magical.

Why Choose Windy City Sailing?

With years of experience and a passion for creating exceptional experiences, Windy City Sailing takes care of all the logistics so you can focus on enjoying the moment. Our knowledgeable crew, top-notch vessels, and commitment to customer satisfaction make us the go-to choice for first-time sailors and seasoned enthusiasts alike.

Your first sailboat charter doesn’t have to be daunting; it should be exciting! Following these steps and partnering with Windy City Sailing guarantees you a seamless and unforgettable day on the water. So gather your group, pick a date, and get ready to set sail.