What you'll do:

You and your crew take over a private boat on Lake Michigan for four hours: cruising Chicago's lakefront, anchoring at The Play Pen, and making the most of a full day on the water with your own sound system, open deck, and room to move.

• Cruise the Chicago skyline: you depart from the harbor and cruise along the lakefront, taking in close-up views of the Chicago skyline that you simply cannot get from shore.

• Anchor at The Play Pen: your captain brings you to Chicago's most popular on-water gathering spot, where you can swim, float, and hang out alongside other boats in a lively open-water setting.

• Jump in and cool off: guests are free to dive off the boat and swim directly in Lake Michigan, making the water itself a core part of the four-hour outing.

• Control the playlist: the vessel runs a premium Bluetooth sound system connected to an onboard iPad with Apple Music, so your group sets the tone from departure to dock.

• Eat, drink, and settle in: you are welcome to bring your own food, beer, wine, and spirits aboard, and a cooler is provided on the boat so everything stays cold.

Four hours on the lake goes faster than expected, so most groups mix time on the move with time anchored at The Play Pen. The boat has enough space to split up: some dancing, some lounging, some in the water.

Why we love it for your party:

• Private charter: your group has the entire vessel to yourselves for all four hours, with no strangers sharing the space.

• The Play Pen access: this is Chicago's go-to on-water spot for swimming and socializing, and arriving by private boat is the best way to experience it.

• Bring your own bar: guests can bring alcohol and food aboard, keeping costs down without sacrificing the party.

• Powerful sound system: the onboard Bluetooth setup connects to Apple Music, so you are not stuck with a pre-loaded playlist or a volume cap.

• Spacious deck layout: there is dedicated space for dancing, lounging, and moving around, so the boat does not feel crowded even with a full group.

About this experience partner:

Wet Again Charters operates private boat charters on Lake Michigan out of Chicago, specializing in group outings for birthdays, bachelor parties, bachelorette parties, and celebration days on the water. Their fleet is equipped with premium Bluetooth sound systems and full deck space for groups that want to move, swim, and stay out for hours. Guests bring their own food and drinks, and the team provides a vetted captain list upon booking for bareboat charter reservations.

Additional information:

• A captain is not included in the base price: for bareboat charters, guests hire a captain separately at $125 to $175 per hour, paid directly. A recommended captain list is provided after booking.

• No glass containers or staining liquids like red wine or cranberry juice: damage fees apply for stains to upholstery or surfaces.

• No denim: denim can dye the seats, which also triggers a damage fee.

• Plan to arrive at least 30 minutes before departure: parking near the harbor is limited and costly, so ride-share is strongly recommended. Factor in walking time from drop-off to the dock.