Looking for a unique way to see Chicago?Trade traffic for tranquility aboard a private sailboat and glide across Lake Michigan. Whether it’s a romantic evening, a laid-back gathering, or a learning adventure, this is your ticket to fresh air, stunning skyline views, and unforgettable moments.

What We Offer

• 1-Hour Private Boat Tour for Six People

• 2-Hour Private Boat Tour for Six People with Fireworks

• 3-Hour Private Sailing Lesson

Good to Know

• BYO Food & Drink: You're welcome to bring your own snacks, meals, and beverages (alcohol allowed — please drink responsibly).

• Restroom Onboard: The boat has a toilet for your comfort during the cruise.

• Scenic Routes: Choose from three different sailing routes, all offering stunning views of the Chicago skyline.

• Amenities Provided: Flatware, cups, plates, and a cooler are included for any items you bring onboard.

• Custom Soundtrack: Bring your music and play it during your cruise.

• Meeting Location: The dock is located just 100 yards north of the Chicago Yacht Club (this is not the exact meeting point).

• More Info Available: For additional details, check out the FAQ page provided by the merchant.

Why You Should Grab This Offer

This isn’t just another city tour—it’s an invitation to escape the crowds and experience Chicago from a completely different angle. Lake Michigan provides the perfect setting to relax, reconnect, or celebrate with those who matter most. Whether you’re sailing past Navy Pier, admiring a sunset behind the skyline, or learning the ropes during a sailing lesson, each experience is designed with personalization and comfort in mind. The flexibility to bring your own food and drinks adds an extra layer of charm, while the routes ensure that no two trips are the same. With the boat docked just north of the Chicago Yacht Club, it’s a breeze to get started. Choose your route, bring your people, and set sail for a memorable time on the water.