Sail & Swim Playpen Party Cruise

What you'll do:

Get the group together for the best Batch party ever! This 4-hour cruise will take you and your guests on a favorable sail from Monroe Harbor along the gorgeous coastline of Chicago's Lakeshore. Party at the playpen or lay low and anchor in a private area on Lake Michigan to swim and float on our Lily Pad and pool floats. Our 37' luxury sailboat is the perfect venue for your celebration. The boat comes complete with everything you need - complimentary beverages and snacks, Bluetooth speakers, private bathroom, changing rooms, refrigerator, and kitchenware.

Why we love it for your party:

• Sail in style (Your private 37’ luxury sailboat comes equipped with everything you need for a first-class celebration on the water)

• Party at the playpen (Anchor in Chicago’s favorite boating hotspot, turn up the music, and soak in the summer vibes with your crew)

• Swim, float, and chill (Make a splash in Lake Michigan with our Lily Pad, pool floats, and all the water toys you need for the ultimate boat day)

• BYOB & sip away (Bring your favorite drinks and snacks—we provide the coolers, glassware, and good vibes for a seamless party experience)

• Unforgettable skyline views (Cruise along Chicago’s iconic waterfront for picture-perfect moments against the city’s breathtaking backdrop)

About this experience partner:

On A Boat Sailing is the premier purveyor of sailing charters & cruises for intimate group celebrations in Chicago. We have over 500 five-star reviews in our seven years in business.

Additional Information:

• What's included:

  • USCG-certified Captain trained in First Aid and CPR (with no separate Captain's fee)

  • Private use of our fully permitted, fully insured sailing yacht (with no fuel or docking fee)

  • Complimentary beverages and snacks on board (with BYOB available)

  • Fully stocked kitchenware, fridge and bathroom (no damage/cleaning deposit)

  • Surround sound Bluetooth speakers

  • Swim platform with ladder, lily pad, life-jackets, noodles, floaties & towels

• What to pack

  • Bathing suit and towel

  • Sunglasses, hat, sunscreen

  • Rain jacket or layers

  • Boat shoes, sandals, light-soled tennis shoes

  • Comfortable, breathable clothes