A group of friends relaxing on the pontoon with the Chicago skyline behind them

See Chicagofrom the water.

Party cruises, sunset skyline runs and float-mat afternoons with Captain Trooper at the helm.

Pick the kind of day you want on the water.

Captain Trooper hosts every trip himself. Tell him your group size and the mood, and he’ll point the boat at the right stretch of the lakefront. Trip length and pricing depend on the day, so call or text for a quote.

Six friends smiling together on the boat with the skyline in the distance

Party cruises

Birthdays, reunions, office escapes. Captain Trooper hosts, so everyone on board gets a good time and nobody has to run the boat.

Guests on the boat at night with glowing skyscrapers rising behind the canopy

Bachelorette and birthday trips

Bring the whole crew, cue the playlist and watch the skyline light up after dark.

The sun dropping toward the horizon over Lake Michigan, seen from the boat

Sunset and skyline runs

Out past the harbor as the sun drops behind the towers. Bring a camera.

Friends floating and waving on a big blue water mat beside the boat

The Playpen

Anchor up with the other boats, hop on the float mat and spend the afternoon in the water.

Looking out from the boat at dusk, a guest seated by the rail and downtown towers lit up across the water

5 of 26

Google reviews
mention safety

Calm when it counts.

A good party boat is fun until something goes wrong. Two guests wrote about the day Captain Trooper stepped in, in their own words.

After docking at the Playpen, her group watched a nearby boat get into trouble.

“He handled the situation very well, contacted the coast guard and the police, and took everyone to safety.”

Anastasia Belozertseva, Google review

During her bachelorette trip, her group’s original boat lost its engines.

“Captain T came to our rescue. We were fighting nasty waves and he calmed all of us down and got us safely onto his boat and back to the dock.”

Nicole Chow, Google review

And the everyday version, from Gordon Skeoch: “Captain was safe, fun, and made us all feel comfortable and prioritized the entire experience.”

From the deck.

Photos from Captain Trooper’s Google listing and from the guests who tagged along. Tap any photo to see it full size.

5.0

26 Google reviews, every one five stars.

Guests mention the safety, the fun and the skyline. Read the rest, or add your own, on Google.

Read all reviews

Sara Allaire
Google review, a year ago
“Captain Trooper did a great job hosting our party and providing a fun experience for all!”
Gordon Skeoch
Google review, a year ago
“Captain was safe, fun, and made us all feel comfortable and prioritized the entire experience.”
haley vanfossen
Google review, a year ago
“We had SO much fun on the boat with captain Trooper!!!! He was so much fun and really cared about our safety.”
23 more guests
left five stars.
See them on Google

The skyline glowing under a sunset sky, photographed by a guest

Tell the captain when and who.

Fill in your pass and send it as a text. It opens in your messaging app, ready to go to Captain Trooper. Prefer to talk it through? Call any day from 7:30 AM to midnight.