easy
4 hours
Accessible for most guests, minimal physical activity required
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!
4 Hour Sail & Swim • Perfect For Bachelor & Bachelorette Parties
Embark on a memorable 4-hour private charter aboard a luxurious 37' sailboat, guided by a USCG-certified captain. Enjoy stunning views of the Lakefront, swim at the Playpen, and indulge in your favorite BYOB snacks. Experience the comfort of a fully-equipped yacht while creating unforgettable memories with your guests.
Our private Wedding Party Cruise will take you & your guests on a favorable sail along the gorgeous Lakefront, giving a unique perspective to the city and a chance to swim at the Playpen. Entwined with comfortable amenities aboard our 37' luxury sailboat, guests will experience Lake Michigan from a privately owned, meticulously-maintained sailing yacht.
✅ USCG-Certified Captain trained in First Aid and CPR.
✅ Private use of our fully-permitted, fully-insured sailing yacht.
✅ Complimentary beverages and snacks on board.
✅ Fully stocked kitchenware, fridge and bathroom.
✅ Stereo surround sound speakers with Bluetooth connection.
✅ Swim platform with ladder, life-jackets, noodles, floaties & towels.
❌ NO Separate captain fee
❌ NO Fuel and docking fee
❌ NO Damage/cleaning deposit
We do our best to have on board everything you might need, some personal items to keep in mind include:
You may bring any food and beverages of your choosing including beer, wine, champagne, or hard seltzers. We have alcohol for purchase on board or ahead of time and can provide catering for an added fee.
If there is current or forecasted lightning or high wind, we make a weather cancellation one hour before your scheduled departure and provide a full refund.
You can see all of our FAQs here on our website
On A Boat Sailing, LLC
info@onaboatsailing.com
312.619.7858
Make sure to arrive at least 30 minutes before your scheduled departure time for a smooth check-in.
Sunscreen, hats, and sunglasses are essential for comfort during daytime cruises.
Bring your own beverages and snacks in a small cooler for convenience and variety.
Monitor weather conditions prior to the trip to ensure a safe and enjoyable experience.
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.
Sunscreen and hats will keep you comfortable during sunny hours.
summer specific
Ideal for swimming at the Playpen stop.
summer specific
Layered clothing for changing weather or cooler evenings.
Capture memorable moments of the cruise.