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Celebrate your special day on a private sailboat cruising Lake Michigan, with stunning skyline views and a customizable itinerary. Perfect for weddings and special gatherings!
Celebrate your special day on a private sailboat cruising Lake Michigan, with stunning skyline views and a customizable itinerary. Perfect for weddings and special gatherings!
Book with On A Boat Sailing
Verified experiences and guided adventures in the surrounding area.
Operated by On A Boat Sailing · Chicago, Illinois
On the picturesque Lake Michigan shoreline, the Wedding Party Cruise offers a stylish and intimate way to celebrate your special day. This private 4-hour charter takes place aboard a sleek 37-foot sailboat, expertly guided by a U.S. Coast Guard-certified captain. The vessel’s spacious deck and luxurious amenities provide a comfortable setting for wedding parties seeking a unique, memorable backdrop. As you cruise, you'll enjoy panoramic views of the Chicago skyline and Lakefront landmarks, perfect for photos or simply soaking in the scenery. The route includes a stop at the popular Playpen, an ideal spot for a swim or a quick dip in the refreshing waters. With a fully-equipped yacht, guests can BYOB and bring along their favorite snacks, making the celebration personalized and relaxed. What truly sets this experience apart is the sense of exclusivity; each cruise is tailored to your party’s needs, whether you're exchanging vows, celebrating an anniversary, or hosting a bachelor/bachelorette party. The Lake Michigan setting combines the thrill of the open water with the comfort of private luxury, making it one of Chicago’s standout water activities. The business’s emphasis on safety, combined with friendly, professional crew, ensures a smooth, unforgettable outing. Six miles from downtown Chicago, this cruise offers a welcome escape from the city hustle, delivering both adventure and elegance in one package. Whether it’s a sunset sail or a daytime celebration, this charter guarantees spectacular views, fresh breezes, and a truly one-of-a-kind experience on one of America’s Great Lakes.
easy.
4 hours.
Accessible for most guests, minimal physical activity required
Yes, the captain can tailor the cruise to your preferences, including special stops or events.
Yes, there is parking available near the departure point in Chicago.
If weather conditions are unsafe, the cruise may be rescheduled or canceled for your safety.
Pets are generally not permitted, but please inquire directly for special accommodations.
The boat comfortably seats up to 12 guests for private charter bookings.
Yes, guests are encouraged to BYOB and enjoy beverages during the cruise.
Lake Michigan has been vital to Chicago’s development as a port city and has hosted numerous historic events and vessel explorations.
The company promotes environmentally responsible boating practices, including waste management and minimal disturbance to local wildlife.
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