Frequently Asked Questions

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How do I book a charter?

To view availability and book online, please click HERE. For special requests, please feel free to contact us by calling our office at 847-714-3644 or emailing

Why should I book through The Playpen Chicago?

Our team is dedicated to providing our customers with the best boating experiences that fit their needs at the lowest prices possible. We partner with the highest rated boat companies in Chicago and can provide our customers with exclusive discounts. By booking through us, you are guaranteed to receive lower prices than if you were to book directly through our partners.

Where are you docked?

Knot My Boat Charters provides all boats listed on our booking platform and they are docked at 31st Street Harbor at 3155 S Lake Shore Drive in Chicago, IL. For directions, please click HERE.

How do I hire a captain?

After booking, Knot My Boat Charters will provide You (the "Charterer") with a confirmation email that includes a list of Operators/Captains for hire that are vetted and familiar with their vessels.

You may choose an Operator/Captain known to You or from a list provided by Knot My Boat Charters. If You would like to provide your own qualified Operator/Captain, please email Knot My Boat Charters at prior so that they may review their credentials and approve them prior to your charter.

How much does a Captain cost?

Operators/Captains typically command $80-120 per hour before gratuity.

It is customary to leave a gratuity to your hired Crew for 15-20% of the total charter price (not to be confused with your Operator/Captain's hourly rate).

Payment and gratuity can be handled directly with your Operator/Captain.

Is there parking available?

Yes, 31st Street Harbors offers plentiful parking options for guests. Please click HERE or more information on 31st Street Harbor and nearby parking options.

What should I bring?

We suggest that all parties to bring:

  • Bottled Water
  • Ice
  • Beverages & Snacks
  • Sunscreen
  • Sunglasses
  • Bathing suit & towel (if swimming)
  • Your Playpen Merch of course!!

Onboard there is a cooler, refrigerator, and bathroom for guests to use.

What is the maximum capacity of each vessel?

Per USCG law, the maximum capacity for a bareboat charter is 1 charterer + 12 passengers before a hired crew.

Please note that the hired Captain/Operators and any additional crew compensated by the Charterer for the reasonable and safe navigation of the vessel are not considered passengers and do not count towards the 12 passenger capacity while under charter.

What is a "bareboat" charter?

Per the USCG, a bareboat charter is a demise charter where the  Charterer (renter) takes temporary ownership of a vessel during the chartered time. As the temporary owner, The Charterer is responsible for the the vessel, his/her Passengers, selecting a capable Operator/Captain, and furnishing his own supplies such as food and drinks. Please note that the Charterer may either operate the vessel or select a competent Operator/Crew to operate the vessel.

A bareboat chartered vessel may not exceed 1 Charterer + 12 Passengers, before a hired crew, regardless while moored, underway, or anchored.

What types of payment do you accept?

Knot My Boat Charters accepts all major credit cards, in addition to Zelle and Venmo. 

Please note that they legally cannot accept payment on behalf of your hired Operator/Captain as they are independent contractors (not employed by or affiliated with Knot My Boat Charters) that are selected and/or hired by the Charterer. 

For crew payment, we suggest reaching out to your hired Operator/Captain directly to discuss their preferred mode of payment.

Are infants and children allowed on board?

Children are allowed! Please note that children do count towards the capacity total and that ages 13 years and younger are required to wear a life jacket at all times. For babies and infants, we highly encourage parents to bring their own infant sized life jackets. 

If parents would like to use Knot My Boat Charters' infant sized life jackets, they ask to please please let them know in advance via phone or email so that their team may prepare them in advance for your reservation.

Can we go on the river?

Absolutely! While this is very common, it is important to note that all vessels must enter/leave through the Chicago Locks when traveling through the Chicago River, which may take up to 1 hour each way on high traffic days. This can quickly occupy the bulk of your charter reservation time, especially during high traffic days like Friday & Saturday afternoons during peak river traffic. To ensure that your charter has ample time and an enjoyable boating experience, we suggest letting both the Knot My Boat Charters team and your Operator/Captain know that you would like to visit the Chicago River prior to your charter date.

What amenities are included?

Each yacht is equipped with a bluetooth sound system, kitchen, restroom, and cooler on board for guests to use.

Additional add-ons are for purchase at charter checkout, such as lily pads.

Can we bring our own food and alcohol?

Yes, all guests are welcome to provide their own food and beverages, including alcohol. Onboard we provide a complimentary cooler, refrigerator, and well-equipped kitchen for you to use.

We suggest avoiding glass containers and staining liquids (like red wine, cranberry juice, etc) as they can damage the upholstery and boat interiors may result in a damage fee.

Each vessel's stove is disconnected for safety and fire prevention reasons and that, consequently, cooking inside the cabins is not possible.

Microwave use is available on each vessel while docked and plugged into shore power. Microwave power cannot be guaranteed while the boat is underway or anchored.

Is there a cooler or refrigerator on board?

Yes, all boats provide a cooler and on-board refrigerator for your use.

Do you offer food & beverage catering?

We do work with several third party preferred caterers that are familiar with both food & beverage catering for pick up and delivery orders. Please reach out to the Knot My Boat Charters team to learn more about our preferred caterers.

Can we play our own music?

Yes, all vessels are equipped with premium upgraded bluetooth sound systems for guests to connect to and enjoy while underway.

Can we bring our own decorations?

Absolutely! Prior to your charter, Knot My Boat Charters requires guests to submit a list of all decoration items for approval. Items such as glitter, confetti, feathered boas, or open flame items (fireworks, sparklers, and candles) are not allowed. Items such as balloons, cakes, costumes, props, watertoys, and flowers are always welcome.

Please note that depending on the timing of other bookings, we cannot always guarantee that guests may be able to board early to set up decorations prior to their charter start time.

Can we go swimming?

Yes, we do allow guests to go swimming during sunlight hours. For your own safety, please note that we do not allow swimming after sunset or if water conditions are unfavorable.

Do you allow tie-ups?

Knot My Boat Charters does NOT allow tie ups while under charter. Referencing USCG bareboat charter guidelines, tie ups increase the risk of illegal bareboat charter activity with guests unknowingly exceeding the 12 passenger capacity restriction.

For group requests over 12 passengers, we do recommend and allow groups to rent multiple vessels and anchor near one another with a minimum of 75' between each vessel. While anchored, guests are able to float, swim, and enjoy the water with passengers from other vessels, however, they are not allowed to board each other's chartered vessel, regardless whether anchored, moored, or underway.

Is there an age requirement?

You must be a minimum of 21 years old to rent and charter a boat as the "Charterer". 

Passengers do not have an age requirement, however. There is no age requirement to be a passenger of the Charterer.

What is the cancellation policy?

Cancellations 14 days or prior to your charter date can be completed on your customer portal and are subject to a 5% service fee. Cancellation requests within 13 days or fewer of your charter date are subject to a 50% cancellation fee and must be requested in writing via email to Please include the following information:

  • Charterer’s Full Name
  • Scheduled Date and Time
  • Written Request for Cancellation
  • Reason for Cancellation

Please note that all rescheduled charterers are exempt from the above-mentioned cancellation schedule (meaning that charterers may not reschedule a charter for a future date and cancel it 14 days or more out in order to receive a full refund).

What is your weather policy?

To ensure guest safety, the Knot My Boat Charters team has the authority to deem whether conditions are “charterable” or “uncharterable” due to weather conditions. Uncharterable weather conditions are typically the result of (but are not limited to) heavy storms, small craft advisory warnings, gale storms, strong winds, and large waves. Light rain, passing storms, and cooler temperatures are typically considered charterable.

In the case that conditions are deemed uncharterable, the Knot My Boat Charters team will work with the charterer to temporarily postpone or reschedule your charter to a future date. In the case of a reschedule, Knot My Boat Charters will issue a rescheduling credit to the Charterer valid up to one year on a charter of equal or lesser value.