Is swimming included in the trip?

Yes, swimming is a key part of the experience when weather permits.

Can we bring food and drinks?

Yes, you’re welcome to bring along snacks, beverages, and even a bottle of champagne for toasts.

Is the trip suitable for children?

Absolutely, families with children are welcome, provided they are comfortable around water.

Comfortable clothing suitable for sailing, plus swimwear and sun protection.

Pets are not typically permitted onboard for safety and comfort.

What happens if the weather is bad?

Trips may be rescheduled or canceled in case of storms or unsafe conditions.

Water Activities & Sail & Swim Playpen Charter on Lake Michigan | Events | Boat Tour

Lake Michigan’s vast shimmering waters set the stage for an unforgettable adventure aboard the S/V Dragonfly, a 37-foot sailing yacht known for its comfort and style. Located in Chicago, this luxurious boat provides an ideal escape for those craving a taste of open water. Whether you're celebrating a special occasion or simply seeking a serene break from city life, the Sail & Swim Playpen Charter delivers an experience steeped in elegance and excitement.

This 4-hour voyage combines the thrill of on-water sailing with the relaxation of swimming in clear lake waters. Under the guidance of a USCG-certified captain, guests are treated to breathtaking panoramic views of Chicago’s skyline, especially during sunset, which casts a warm glow over the water. The yacht comes fully equipped with amenities for comfort, including a shaded deck, cushioned seating, and a champagne toast to mark the moment.

What makes this trip unique? It’s the perfect synergy of luxury and adventure in an iconic Midwest setting. The boat’s sleek design and well-maintained state ensure a smooth sail, while the inviting swim area offers a refreshing escape. The captain’s knowledge of Lake Michigan's local history and natural features adds an educational touch, making the experience both fun and informative.

This adventure is suitable for small groups, families, or couples looking for a private, high-end outing on the water. The trip’s flexibility allows customization—whether you want to anchor for a swim, enjoy a scenic sail, or simply unwind with good company. No matter your experience level, this sail and swim voyage brings a splash of luxury and a dash of adventure to Chicago’s shores.

Ready to cast off? The Sail & Swim Playpen Charter promises an immersive lake experience, blending spectacular scenery with onboard comfort. It’s a standout way to enjoy Lake Michigan’s natural beauty in style and ease.