THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel
Set sail on Lake Michigan aboard the luxurious S/V Dragonfly for a four-hour adventure filled with scenic views and refreshing swims. Discover why this high-end charter is a top choice for water lovers in Chicago.
Set sail on Lake Michigan aboard the luxurious S/V Dragonfly for a four-hour adventure filled with scenic views and refreshing swims. Discover why this high-end charter is a top choice for water lovers in Chicago.
Book with On A Boat Sailing
Verified experiences and guided adventures in the surrounding area.
Operated by On A Boat Sailing · Chicago, Illinois
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.
easy.
4 hours.
All levels; moderate physical activity involved in swimming.
Yes, swimming is a key part of the experience when weather permits.
Yes, you’re welcome to bring along snacks, beverages, and even a bottle of champagne for toasts.
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.
Trips may be rescheduled or canceled in case of storms or unsafe conditions.
Lake Michigan has been vital to Chicago’s development, with shipping and trade dating back over a century.
The charter operators follow sustainable practices to minimize environmental impact and protect Lake Michigan’s natural beauty.
On A Boat Sailing is a Chicago-based private charter company offering curated sailing and yachting experiences on Lake Michigan. The company specializes in a range of private cruises including skyline sunset sails, lakefront sightseeing, swim-and-sail playpen outings, wedding and wedding-party charters, engagement and proposal cruises, Navy Pier fireworks cruises, and group yachting aboard larger vessels. Trips operate aboard a fleet that includes a 37' sailboat, the S/V Dragonfly, and the larger Yacht Guppy for big groups. Each charter includes a USCG-certified captain responsible for navigation, safety briefings, and a professionally managed experience. Add-on services include premium drink packages with pre-ordered wine, champagne, beer, and seltzer, and guests are welcome to bring BYOB snacks and beverages on most cruises. Bookings are designed for private groups seeking a tailored event on the water, from romantic two-hour engagements to four-hour celebration charters and three-hour fireworks cruises. On A Boat Sailing highlights clear departure logistics from Chicago waterfront locations and offers complimentary light snacks and select beverages on several trips. Safety and comfort are emphasized through certified captains, fully equipped yachts, and adherence to local maritime regulations. The business is positioned for authentic Lake Michigan experiences, delivering skyline views, swimming stops, and customizable itineraries for family gatherings, corporate outings, and special events. On A Boat Sailing provides transparent trip summaries, duration options, and vessel details so prospective guests can choose the best private charter for their occasion. Seasonal options.
Book with On A Boat Sailing