How to rent a boat for the playpen: #1 Ultimate

Introduction: Welcome to Chicago’s Ultimate On-Water Playground

How to rent a boat for the playpen is simpler than you might thinkand it opens the door to one of Chicago’s most exclusive on-water experiences. Here’s what you need to know:

1. Determine your group size (most boats hold 9-20 guests)
2. Choose between a captained charter (captain included, no license needed) or bareboat rental (you provide the captain)
3. Book early (especially for summer weekends and special events)
4. Expect to pay $200-$400+ per hour, plus captain fees and gratuity
5. Reserve through platforms like Playpen Chicago or directly with local charter companies

The Playpen is Chicago’s famous floating social huba section of Lake Michigan just off Oak Street Beach where boats anchor together for parties, celebrations, and unforgettable days on the water. With the iconic Chicago skyline as your backdrop, it’s become the go-to destination for bachelor parties, bachelorette celebrations, birthdays, and corporate events.

According to Chicago Scene Boat Party owner Ted Widen, who’s been hosting parties in the Playpen for over 20 years: “You are Guaranteed to have a great time!”

The Playpen isn’t just about renting a boatit’s about joining a vibrant boating community where luxury yachts raft up alongside sport boats, music plays across the water, and exclusive events like the Glow in the Dark Yacht Party bring hundreds of boaters together under the stars.

Why rent a boat for the Playpen? Because it’s the only way to access this floating party scene. You can’t walk there, swim there, or get invited unless you’re on a boat. Whether you’re looking to host your crew on a private charter or purchase a seat on someone else’s vessel, renting a boat is your ticket to Chicago’s most sought-after summer experience.

Step 1: Choosing Your Perfect Playpen Vessel

When we set out to rent a boat for the Playpen, the first thing we need to consider is our group size, what our budget looks like, and what kind of activities we have in mind. These factors will directly influence the type and size of boat that’s perfect for our Playpen adventure. Whether we’re planning a lively party or a relaxed day of sunbathing and swimming, there’s a vessel out there for us.

Types of Boats Available for a Playpen Adventure

Chicago’s Lake Michigan offers a fantastic array of boats suitable for the Playpen, catering to every taste and group dynamic. From nimble sport boats to spacious luxury yachts, we have plenty of options to make our day unforgettable.

• Sport Boats: These are typically 30-40 feet in length, like the Rinker Fiesta Vee or Sea Ray Sundancer models. They’re excellent for day trips, river cruises, and getting to the Playpen with speed and style. They offer a good balance of comfort and agility. For instance, a 33’ Rinker Fiesta Vee might start around $200 per hour, while a 37’ Sea Ray Sundancer could be around $262.50 per hour.
• Pontoon Boats: Often described as “party huts,” pontoon boats like a 30-foot Sun Tracker Pontoon are fantastic for groups looking for a relaxed, social experience. They offer ample deck space, comfortable seating, and often come equipped with amenities like sound systems, blenders, and even water guns! These vessels comfortably seat up to 12 people. A luxury large pontoon boat can accommodate up to 12 people.
• Luxury Yachts: For those seeking the ultimate in comfort and sophistication, luxury yachts ranging from 40-70 feet are available. These “Premium” (40-50′) and “Luxe” (50-70′) vessels, such as the Sea Ray Express or Sea Ray Sun Sport, often feature air-conditioned cabins, full kitchens, and state-of-the-art entertainment systems, making them perfect for longer outings or more upscale events. Rates for these can range from $275 per hour for a 50′ Sea Ray Sundancer to $387.50 per hour for a 70′ Sea Ray Sun Sport.
• Sailing Yachts: While less common for the high-energy Playpen party scene, a sailing yacht like the 37′ S/V Dragonfly offers a unique “Sail & Swim” experience, combining the thrill of sailing with anchoring for water activities. These often cater to smaller, more intimate groups, typically up to 7 guests, and usually include a captain.

Here’s a quick comparison to help us decide:

Boat Type	Capacity (Typical)	Typical Cost (Hourly)	Best Use Case
Sport Boats	9-12 people	$200 – $275	Day trips, river cruises, fast Playpen access
Pontoon Boats	8-12 people	$210 – $300	Relaxed parties, social gatherings, casual fun
Luxury Yachts	12-20 people	$275 – $387.50+	Upscale events, longer outings, ultimate comfort
Sailing Yachts	6-7 people	$250 – $300	Intimate groups, unique sailing & swimming experience

Captained Charter: The Easiest Way to Enjoy the Playpen

When we’re figuring out how to rent a boat for the playpen, one of the most significant decisions is between a captained charter and a bareboat rental. For most of us, a captained charter is the easiest and most enjoyable way to experience the Playpen.

A captained charter means the boat comes with a professional, USCG-licensed captain, and sometimes even additional crew. Our job? Simply show up, relax, and celebrate! The captain handles all navigation, safety, and operational aspects of the boat. This means we don’t need any prior boating experience or a boating license ourselves. It’s an all-inclusive experience where we can focus entirely on having fun with our friends and soaking in the Chicago skyline. For example, a 4-hour private charter for up to 7 guests on a sailing yacht includes a USCG Captain, with no hourly captain fees or surprise charges.

In contrast, a bareboat rental means we rent just the vessel itself and are responsible for providing our own qualified captain. While this offers more control and flexibility for experienced boaters, it adds a layer of responsibility and planning. For a hassle-free Playpen experience, especially for parties and social events, we highly recommend a captained charter. Many rental services, including those listed on the Playpen Chicago platform, primarily offer captained charters for the Playpen.

How to Choose the Right Boat Size for Your Group

Choosing the right boat size is critical for both comfort and safety. Our headcount directly impacts the kind of boat we’ll need, as every vessel has a strict capacity limit.

• Small Groups (2-7 people): For more intimate gatherings, a smaller sport boat or a sailing yacht like the S/V Dragonfly (7 guests) is ideal. These boats offer a cozy atmosphere and can be more budget-friendly.
• Medium Groups (8-12 people): This is the sweet spot for many Playpen charters. Pontoon boats (up to 12 people) or mid-sized sport boats (e.g., 30-40 ft) are excellent choices. Boats like the XOXO – ROAM pontoon comfortably seat 12 passengers, ensuring everyone has space to relax and party.
• Larger Groups (12-20 people): Many larger charters can hold between 9-20 people. If our group is on the higher end, we might need a larger luxury yacht (40-50 ft or even 50-70 ft). Some owners even have multiple boats that can “tie-up” together in the Playpen to accommodate bigger parties, like Ted Widen’s ability to combine his 35′ and 51′ Sea Ray Sundancers for up to 25 people.

Capacity limits are mandated by the U.S. Coast Guard for safety. We cannot exceed these limits, so keeping our numbers tight and accurate when booking is essential. For more detailed information on exclusive boat charters and finding the perfect fit for your group, explore our options for More info about exclusive boat charters.

Step 2: The Ultimate Guide on How to Rent a Boat for the Playpen

Once we’ve decided on the type of boat, the next step is to steer the booking process. This involves understanding when to book, what costs to expect, and what happens if plans change.

Planning and Booking Your Charter

When we’re trying to figure out how to rent a boat for the playpen, timing is everything. Chicago’s boating season is vibrant but relatively short, typically from spring to early fall, and demand for Playpen charters is incredibly high, especially during the summer.

• Book Early, Especially for Peak Times: Summer weekends, holiday weekends (like the 4th of July or Labor Day), and popular events (like the Chicago Air & Water Show or Lollapalooza) book up fast. We’re talking months in advance for prime dates. For example, Ted Widen, a seasoned Playpen host, advises us to “reserve ASAP as boats book up early.” If we want to guarantee our spot for a sunset cruise or a specific event, early booking is non-negotiable.
• Booking Windows: While some shorter rentals (less than 3 days, though this is less common for Playpen charters) might be booked just a couple of days in advance in other locations, for Chicago’s Playpen, think weeks to months. For events like the “Glow in the Dark Yacht Party,” organizers strongly recommend booking early to ensure availability.
• Midday vs. Sunset vs. Evening: We have timing options that offer different experiences. Midday cruises are perfect for sunshine and Playpen visits, while sunset sails offer breathtaking city views and are highly requested. Evening charters can transition us into Chicago’s nightlife.
• Making the Reservation: Most platforms and charter companies require a deposit, often 50%, to secure our booking. The remaining balance is typically auto-debited a few days before the reservation. For an incredible sailing and swimming experience, consider a Sail & Swim Playpen Charter for your group.

Understanding Costs and Inclusions

Let’s talk numbers! The typical cost of renting a boat for the Playpen can vary significantly, but we can break down the key components:

• Hourly Rates: As we saw earlier, hourly rates can range from approximately $200 for smaller sport boats or pontoons to over $387.50 for larger, more luxurious yachts. Most rentals have a minimum duration, often 3-4 hours. For example, the XOXO – ROAM pontoon has a minimum rental of 4 hours at $300 per hour.
• Captain Fees: For captained charters, the captain’s fee is a significant component. Some all-inclusive charters, like the Sail & Swim Playpen Charter, include the captain’s fee in their listed price. However, for others, the captain fee might be separate, such as $100 per hour for the XOXO – ROAM boat. Captains are typically independent contractors, not employees of the rental company.
• Fuel Costs: Fuel can either be included in the rental price (as with some all-inclusive charters) or charged separately based on consumption. If it’s separate, we’ll usually start with a full tank and pay for what we use at the end of our trip.
• Gratuity: It’s customary to tip our captain and any crew for excellent service. A gratuity of 10-20% of the total charter fee is generally recommended and greatly appreciated. This can often be paid directly to the captain via cash, Venmo, or Zelle.
• Security Deposits: A security deposit, usually a hold on our credit card rather than an actual charge, is common practice to cover any potential damages. This hold is released after the rental is complete and if no claims are made.

What’s Typically Included vs. Extra Costs:

• Typical Inclusions:
  • USCG-licensed captain (for captained charters)
  • Life jackets and other safety equipment
  • Coolers and ice
  • Basic amenities like sound systems (often Bluetooth-enabled)
  • Sometimes water toys (e.g., water guns, inflatable rafts)
  • Refueling and docking fees (for some all-inclusive charters)
• Potential Extra Costs:
  • Captain fees (if not included in the base rate)
  • Fuel (if not included)
  • Gratuity for captain and crew
  • Optional add-ons like catering, jet ski rides, photography, or special decorations
  • Marina entry fees (less common in Chicago, but good to be aware of)
  • Cleaning fees (if the boat is left excessively messy, especially with pets)

Decoding Cancellation Policies

Life happens, and sometimes plans change. Understanding the cancellation policies for Playpen boat rentals is crucial. These policies can vary between providers, so always read the fine print!

• Cancellation Windows: We’ll generally find tiered refund structures based on how far in advance we cancel:
  • 15+ days in advance: Often a 100% refund.
  • 8-14 days in advance: Sometimes a 50% refund.
  • Within 7 days: Usually no refund, but sometimes options to reschedule.
  • Within 24-48 hours: Typically no refund. Ted Widen’s charters offer free cancellations up to 24 hours before the booking, but within 24 hours, it’s non-refundable. The Sail & Swim Playpen Charter offers 100% refund up to two weeks out, and 50% up to 48 hours.
• Weather-Related Cancellations: This is a big one on Lake Michigan! Most reputable charter companies have a clear bad-weather policy. Cancellations due to unsafe weather conditions (e.g., heavy winds, storms) are usually initiated by the captain for safety reasons. In such cases, we typically receive a 100% refund or the option to reschedule without penalty. However, it’s important to note that rain alone might not always trigger a cancellation, and if a trip is cut short due to weather, a partial refund may not be guaranteed.
• Rescheduling Options: Many companies are flexible and will work with us to reschedule our charter if we need to cancel outside of the full refund window, subject to availability. This is often a better option than losing our entire payment.

Step 3: Prepping for a Safe and Unforgettable Day on the Water

Now that our boat is booked, it’s time to get ready for an epic day! A little preparation goes a long way in ensuring a safe, enjoyable, and unforgettable Playpen experience.

Your Essential Playpen Packing List

To make sure we have everything we need for a fantastic day on Lake Michigan, here’s a checklist:

• Sun Protection: Sunscreen (crucial! but avoid spray-on sunblock as it can damage boat surfaces), sunglasses, and hats.
• Swim Gear: Swimsuits, towels, and maybe a change of clothes if we plan on taking a dip.
• Food and Drinks: Most rentals are BYOB-friendly, and we can bring our own food. However, there are some important rules:
  • NO GLASS CONTAINERS! This is a universal safety rule on boats. Opt for cans or plastic bottles.
  • Avoid red wine or brightly colored beverages/foods (like red/blue/purple drinks) that can easily stain boat upholstery.
  • Bring plenty of water to stay hydrated.
  • Many boats provide coolers and ice, but we should confirm this beforehand.
• Music: Bring a downloaded music playlist! Wi-Fi isn’t always reliable on the lake, but most boats have excellent Bluetooth sound systems ready for our tunes.
• Essentials: Our ID and the credit card used for the booking (for verification), any necessary medications, and a waterproof bag for electronics.
• Comfort Items: Flip-flops or boat shoes (some boats require shoes off, providing shoe bags), light jackets or cover-ups for cooler breezes.

How to rent a boat for the playpen and ensure a safe trip

Safety is paramount on the water, and we want everyone to have a blast without any worries. Here’s how we ensure a safe and enjoyable experience:

• Listen to Your Captain: This is the golden rule! Our USCG-licensed captain is the ultimate authority on the boat. They are responsible for our safety and the vessel’s operation. Their instructions should always be followed without question. The captain may return guests to the dock for safety risks, extreme intoxication, or refusal to follow instructions.
• Life Jacket Requirements: While adults aren’t typically required to wear life jackets at all times on a charter, children are a different story. In Illinois, children under 13 years of age are generally required to wear a life jacket while on a moving vessel. Confirm any specific requirements with our charter company, and if we have infants, it’s best to bring our own infant-sized life jackets, notifying the company in advance.
• Boating License Requirements for Rental Boats: If we opt for a bareboat rental (where we drive the boat ourselves), we’ll need to meet specific requirements. Generally, to rent and operate a boat with a motor, we must be at least 18 years old. For those born on or after January 1, 1988, a Boater Safety Card is typically required. Even if we’re born before this date, some companies might require previous boating experience. If we don’t have a license, some providers might offer a brief safety exam. For more information on boating safety and licensing, we can check official resources from the Illinois Department of Natural Resources. However, with a captained charter, we don’t need to worry about any of these requirements!
• Respect Capacity and Weight Limits: Boat capacity limits (both passenger count and total weight) are strictly enforced for safety. We must ensure our group does not exceed these limits, including infants.
• Stay Hydrated and Pace Ourselves: Sun and alcohol can be a potent combination. Drink plenty of water throughout the day.
• Designate a Trip Coordinator: It’s often helpful to have one person in our group act as the primary contact with the captain.

Playpen Rules, Activities, and Special Events

The Playpen isn’t just a place; it’s an experience with its own set of unwritten rules and vibrant activities.

• Rules and Regulations:
  • No-Wake Zone: The Playpen is generally a no-wake zone, meaning boats must proceed at a slow speed that creates minimal waves.
  • Anchoring: Boats anchor together in the Playpen, forming a floating community.
  • Tie-Ups: While spontaneous tie-ups between private boats are common, recent US Coast Guard regulations mean that charter boats are typically not permitted to tie-up directly to other charter boats. Our captain will anchor in a safe and suitable spot near other boats.
  • No Smoking: Many charter boats have a strict no-smoking policy on board, though e-cigarettes or vapes might be permitted.
  • Shoes Off: It’s common practice to remove shoes before boarding to protect the boat’s surfaces.
• Popular Activities:
  • Swimming and Floating: Once anchored, it’s common to jump in the refreshing waters of Lake Michigan, swim, and float around with friends.
  • Sunbathing: Lounge on the deck, soak up the sun, and enjoy the stunning skyline views.
  • Partying and Socializing: The Playpen is famous for its party atmosphere. Music, laughter, and good vibes are always in abundance.
  • Water Toys: Some boats come with water guns or inflatable rafts for extra fun.
• Special Events: The Playpen is a hub for themed parties and major Chicago events:
  • Glow in the Dark Yacht Party: Imagine electrifying lights, high-energy beats, and an epic foam party under the stars. These events often require an official event flag for participation.
  • Fireworks Cruises: Witness Chicago’s spectacular fireworks displays from the unique vantage point of Lake Michigan, often on Wednesday and Saturday nights.
  • Chicago Air & Water Show: Renting a boat is one of the best ways to experience this incredible aerial display up close. These dates are highly sought after.
  • Lollapalooza: While not directly in the Playpen, many boaters enjoy listening to the concert from Monroe Harbor, turning it into a unique on-water concert experience.

To stay updated on all the exciting happenings and find when to experience these events, explore our Discover Chicago boating events.

Frequently Asked Questions about Playpen Boat Rentals

What is the first step in how to rent a boat for the playpen?

The very first step in how to rent a boat for the playpen is to determine your group size, set a realistic budget, and decide on the type of activities you envision. This foundational planning will guide all subsequent decisions. Once you have a clear idea of these factors, we recommend choosing between a captained charter (for ease and convenience) or a bareboat rental (if you have a qualified captain in your group). This initial clarity makes the booking process much smoother.

Do I need a boating license to rent a boat in Chicago?

If you opt for a captained charter, no, you do not need a boating license. The licensed USCG captain onboard will operate the vessel. This is the most common and recommended option for Playpen outings. However, if you choose a bareboat rental and intend to operate the boat yourself, you will need to meet Illinois boating license requirements. Generally, to operate a boat with a motor, you must be at least 18 years old. If you were born on or after January 1, 1988, you typically need a Boating Safety Certificate. Individuals between 12-17 years old also have specific requirements. For most Playpen partygoers, a captained charter bypasses these requirements entirely.

What is the typical cost of renting a boat for the Playpen?

The typical cost of renting a boat for the Playpen varies widely based on boat type, size, duration, and whether a captain is included. We can expect hourly rates to range from approximately $200 for smaller sport boats or pontoons to over $400 for larger luxury yachts. Most rentals have a minimum duration of 3-4 hours. Captain fees, if separate, can add around $100 per hour. Don’t forget to factor in fuel costs (if not included), and a customary 10-20% gratuity for your captain and crew. For example, a 4-hour charter on a mid-sized boat could cost anywhere from $800 to $1,500+ before gratuity, depending on the vessel and inclusions.

Conclusion: Your Unforgettable Chicago Experience Awaits

Renting a boat for the Playpen is more than just a transaction; it’s your gateway to an unparalleled Chicago experience. From the initial excitement of choosing your perfect vessel to the joyous moments spent with friends against the stunning city skyline, every step is part of an unforgettable adventure. We’ve walked through the essential steps, from selecting the right boat and navigating booking logistics to packing smart and ensuring a safe, fun-filled day.

The Playpen isn’t just a location; it’s a vibrant social hub, a place where memories are made, and Chicago’s unique boating culture truly comes alive. So gather your crew, pick your perfect boat, and get ready to dive into the heart of Lake Michigan’s premier party destination. Your unforgettable Chicago experience awaits, and we’re here to help you open up it. Join our community and find even more about Chicago’s boating scene and exclusive events by visiting Join the Playpen Chicago community.