CHICAGO BOAT TOUR FIELD GUIDE
Beach Please: Private Large-Boat Charters Off Chicago for Groups Up to 13
Private charters run 3–8 hours (rates from $1,050) aboard spacious large boats equipped with Bluetooth stereo and a Yeti cooler.
Beach Please: Private Large-Boat Charters Off Chicago for Groups Up to 13.
Adventure brief
Beach Please: Private Large-Boat Charters Off Chicago for Groups Up to 13
Beach Please is a private large-boat charter out of Chicago that puts groups aboard roomy vessels with indoor and outdoor areas, Bluetooth stereo and a Yeti cooler; trips are fully crewed and customizable with your choice of captain.
Chicago’s sweeping lakefront offers a fresh perspective from the water, where urban skyline views meet the dynamic pulse of Lake Michigan. Aquatainment, LLC’s signature trip, Beach Please, invites adventurers to seize the day aboard a large, well-appointed boat designed for comfort and flexibility. With indoor and outdoor seating and an integrated Bluetooth stereo system, this vessel turns a simple charter into a personalized aquatic escape.
Operating out of the city’s southern reaches, Beach Please creates an ideal platform for both social gatherings and tranquil scenic cruises. Its substantial size accommodates groups up to 13, making it perfect for everything from intimate celebrations to larger meetups. Captains are provided to steer the course, allowing passengers to fully immerse in the experience without worry. Guests are encouraged to bring their own food and beverages, turning the boat into a moving private picnic out on the water.
What makes this experience stand apart is its approachability and customization. Chicago’s harbor, along with proximate bays and channels, offers a unique natural backdrop framed by the striking juxtaposition of city architecture and open water. The route you take can be adjusted depending on your interests—whether that means cruising past famed landmarks like Navy Pier or venturing toward calmer waters ideal for relaxing.
Beyond the cool breeze and open skies, this activity shines in bringing the local outdoor recreation scene to the water itself. Aquatainment, LLC bridges urban adventure with the tranquility of the lake, delivering a seamless blend of access and escape. It’s a distinctive option for visitors who want a day on the water that feels crafted specifically for them.
Whether you’re new to boating or a seasoned lake enthusiast, Beach Please is an invitation to see Chicago from an exceptional vantage point. It’s an accessible, enjoyable way to connect with the city’s aquatic environment and enjoy a memorable day under the sun and sky.
Route Schematic
Itinerary Schematic
Typical charters follow a simple board–cruise–return flow; specifics are customizable with your captain.
Boarding & departure
Guests board the large boat and depart under the captain’s direction to begin the charter.
Open-water cruise
The boat spends the bulk of the charter cruising the waters while guests use indoor and outdoor areas and the onboard stereo.
Return & disembark
At charter end the captain returns the vessel to the pickup point and guests disembark, taking their gear and rubbish with them.
Operators require a captain and may adjust routing; follow the captain’s safety guidance and be prepared to manage your own food, drink and waste at trip end.
Highlights
Outing Highlights
Roomy, well-equipped vessels
Each charter is on a large boat fitted with indoor and outdoor spaces, a Bluetooth stereo system and a Yeti cooler—setups intended for relaxed days on the water.
Charter with your choice of captain
All charters require a captain; the operator provides a list of captains and related information in the confirmation so you can tailor the crew to your group.
Multiple durations to match your plan
Charters are offered in increments from 3 to 8 hours, letting you choose the length that fits your gathering and schedule.
What the day feels like
What the day feels like
The outing is a private boat charter that places your group aboard a large vessel for a multi-hour cruise; you supply food and drink, pick a captain from the operator’s roster, and spend the charter moving between indoor and outdoor spaces aboard the boat.
Suitability
Who it's for
Who this charter suits—and who should consider alternatives.
Practical planner
Details to review before reserving
Bring your own food and drink (including water and ice). Also bring cups, plates and any serving gear you need. You are responsible for removing all items and rubbish at trip end; a damages fee may be charged for excessive filth.
Boats include a Bluetooth stereo and a Yeti cooler, plus indoor and outdoor areas for guests to use during the charter.
A 50% deposit is required to secure booking; additional confirmation materials—such as a list of captains and captain information—are provided after booking.
Review cancellation policies before reserving.
Frequently asked questions
Planning Your Outing
Is a captain provided with the charter?
All charters require a captain; the operator will send a list of captains and related information in your confirmation email.
How is the captain paid?
The captain’s fee is separate from the charter rate and is paid directly to the captain.
What about gratuity for the operator?
A customary gratuity to the operator is 15–20% of the total fee.
Do I need to bring food and drink?
Yes—guests should bring their own food and drink, plus water and ice; bring cups, plates and other serving items you need.
Is a deposit required to book?
A 50% deposit is required to secure booking of the yacht.
What happens to rubbish after the charter?
Guests are asked to take all items and rubbish with them when departing; a damages fee may be charged for excessive filth.
How this guide was prepared
This field guide is synthesized using verified supplier specifications, route descriptions, and destination data. Some booking links may generate affiliate revenue for ADV Guides.
- Verified: 2026-09-08T19:50:48.931Z
Some booking links may generate revenue for ADV Guides or The Adventure Collective.
Availability, pricing, schedules and operating details can change.
Trip details and contextual sources were reviewed by ADV Guides Editorial.