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Navy Pier Chicago: Private Sailboat Charter with Captain

Chicago, USA
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from $1,109 per group (up to 7)

Lowest Price Guarantee
Navy Pier Chicago: Private Sailboat Charter with Captain Image 1
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3 hours (approx.)
Mobile ticket
Instant confirmation
Offered in: English

Overview

On A Boat Sailing offers an all-inclusive, private VIP sailing experience departing from the brand-new Navy Pier Marina in Downtown Chicago. If you appreciate attention to detail, hospitality, and sophisticated service, this is the boat rental for you! Amenities on board include:

Pricing for private groups up to 7 guests.
Custom pricing available for larger groups up to 12.
Anchoring in the Chicago Playpen for swim and float parties.
Swim platform with rinse shower-lily pad, noodles, life-jackets and floaties.
Large open cockpit seating area.
Complimentary beverages and snacks or BYO (alcohol allowed).
Stereo surround sound speakers with Bluetooth connection.
Fridge with ice, fully stocked kitchenware.
Skyline views of Downtown Chicago, Navy Pier and the Chicago Lighthouse.
Anchoring for concerts at Northerly Island.
Kitchen, bathroom and changing room on board.

What's Included

  • Snacks
  • Carbonated beverages Soda/Pop
  • Bottled water
  • Alcoholic beverages Available for purchase or BYO
See 1 moreSee 1 more

Meeting Location

Meeting point

797 East Grand Avenue
Chicago, IL 60611, USA

Show on Google Maps

Detailed check-in instructions, including the exact address, are provided with your booking confirmation.

End point

This activity ends back at the meeting point.

What To Expect

On A Boat Sailing offers an all-inclusive, VIP sailing experience departing from the brand-new Navy Pier Marina in Downtown Chicago. If you appreciate attention to detail, hospitality, and sophisticated service, this is the private boat rental for you! Amenities on board include:

Pricing for private groups up to 7 guests.
Custom pricing available for larger groups up to 12.
Anchoring in the Chicago Playpen for swim and float parties.
Swim platform with rinse shower-lily pad, noodles, life-jackets and floaties.
Large open cockpit seating area.
Complimentary beverages and snacks or BYO (alcohol allowed).
Stereo surround sound speakers with Bluetooth connection.
Fridge with ice, fully stocked kitchenware.
Skyline views of Downtown Chicago, Navy Pier and the Chicago Lighthouse.
Anchoring for concerts at Northerly Island.
Kitchen, bathroom and changing room on board.

No added fees for fuel, security deposit, cleaning or water toys. Fully licensed, permitted and insured boat operating at the highest safety standards set and maintained by the US Coast Guard.

Additional Info

  • Confirmation is instant and will be received at time of booking
  • Service animals allowed
  • Public transportation options are available nearby
  • Suitable for all physical fitness levels
  • Infants and small children can ride in a pram or stroller
  • Infants are required to sit on an adult’s lap

Frequently Asked Questions

(8)

Q: Will I get seasick on Navy Pier Chicago: Private Sailboat Charter with Captain?

A: If you have any doubts about becoming seasick on the water, we recommend taking a Dramamine® Motion Sickness Relief tablet the night before your trip. Some people recommend taking it the night before your cruise and then again that morning so you will not feel so drowsy. Read more Feb 2023

Cancellation Policy

You can cancel up to 24 hours in advance of the tour for a full refund.

Still have questions?

We're here to help.
Activity code: C-5647184P1


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Frequently Asked Questions (8)

Activity name

The answers provided below were previously given in response to questions from Cool Destinations customers.

Filter by:

Q: Will I get seasick on Navy Pier Chicago: Private Sailboat Charter with Captain?
A:

If you have any doubts about becoming seasick on the water, we recommend taking a Dramamine® Motion Sickness Relief tablet the night before your trip. Some people recommend taking it the night before your cruise and then again that morning so you will not feel so drowsy.

Feb 2023
Q: What is the cancellation policy for the Navy Pier Chicago: Private Sailboat Charter with Captain?
A:
You can cancel up to 24 hours in advance of the tour for a full refund.
  • For a full refund, you must cancel at least 24 hours before the tour start time.
  • If you cancel less than 24 hours before the tour start time, the amount you paid will not be refunded.
  • Any changes made less than 24 hours before the tour start time will not be accepted.
  • Cut-off times are based on the tour local time (CDT).
Apr 2025
Q: What's included in the price?
A:
The following is included:
  • Snacks.
  • Carbonated beverages. Soda/Pop.
  • Bottled water.
  • Pool floats, rafts and towels.
The following is NOT included:
  • Alcoholic beverages. Available for purchase or BYO.
Apr 2025
Q: What is the weather cancellation policy?
A:

This tour requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.

Apr 2025
Q: What is the minimum age for this tour?
A:

There is no minimum age for this tour, so bring your wee one along for an adventure..

Apr 2025
Q: My date is not available in the calendar, I am just checking to see if it is available?
A:

If a date or time is not listed on the calendar, it’s sold out or unavailable for another reason. Support cannot assist further if a date or time is not on the calendar.

If you find a date and time that works for you, book it NOW because things always sell out at this time of year.

Apr 2025
Q: Is this an accessible tour?
A:

Accessibility information for the Navy Pier Chicago: Private Sailboat Charter with Captain is as follows:

  • Service animals allowed
  • Public transportation options are available nearby
  • Not recommended for travelers with spinal injuries
  • Suitable for all physical fitness levels
Apr 2025
Q: Where is the meeting point for this activity?
A:

Detailed check-in instructions – including meeting point address, Google map, and parking information – for Navy Pier Chicago: Private Sailboat Charter with Captain will be included in your confirmation email from Cool Destinations. Please be sure to double and triple check your email address is correct at checkout so this important email makes its way to you!

 

 

Mar 2024

What's Included

Activity name

  • Snacks
  • Carbonated beveragesSoda/Pop
  • Bottled water
  • Pool floats, rafts and towels
  • Alcoholic beveragesAvailable for purchase or BYO

Additional Info

Activity name

  • Confirmation is instant and will be received at time of booking
  • Service animals allowed
  • Public transportation options are available nearby
  • Not recommended for travelers with spinal injuries
  • Suitable for all physical fitness levels
  • Infants and small children can ride in a pram or stroller
  • Infants are required to sit on an adult’s lap
  • Operated by a business

Protecting you

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For your protection and stress-free bookings, use our secure platform to pay for bookings. On A Boat Sailing

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Lowest Price Guarantee

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We guarantee the lowest price on all the tours available to book on our site. We'll refund the difference if you find the exact tour cheaper online until 48 hours before your tour starts.

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Locate your Cool Destinations Booking Number and the proof of the lower price you found.

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Email priceguarantee@mybookings.zendesk.com with the documents, your name, and your home address.

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We'll review your materials and get in touch as soon as possible.

Receive your refund

If everything checks out, we'll refund you the price difference.

Refund Terms & Conditions

The following conditions apply to all lowest price guarantee refund requests:

  • The lowest price guarantee is available to any customer who makes a qualifying purchase through our website. The qualifying purchase must be a minimum of US$20 (or equivalent).
  • The lowest price guarantee covers retail and prepaid rates available to the general public. This does not include discounts or promotions you may receive (or be eligible for) from third-party sites or organizations such as AAA or AARP or special offers made as part of a membership program, corporate discount, daily deal, group, or rewards program.
  • Cool Destinations promotions cannot be combined with the lowest price guarantee.
  • If you find a lower retail or prepaid rate for the same tour, offered on the same date, time and priced in the same currency as your original purchase, on any other website between the time you book on Cool Destinations and 48 hours before your trip starts, we will refund the difference.
  • The lowest price guarantee does not apply where a lower overall price is found by breaking down the purchased tour into one or more parts sold separately.
  • Cool Destinations reserves the right to verify the lower price details. Examples of acceptable forms of verification include a web screenshot or a web address.
  • All refund decisions will be made at the sole discretion of Cool Destinations.
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Free Cancellation

100% refund
No refund

You can cancel up to 24 hours in advance of the tour for a full refund.

  • For a full refund, you must cancel at least 24 hours before the tour start time.
  • If you cancel less than 24 hours before the tour start time, the amount you paid will not be refunded.
  • Any changes made less than 24 hours before the tour start time will not be accepted.
  • Cut-off times are based on the tour local time (CDT).
  • This tour requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.

Sorting, ranking, and search results

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Cool Destinations wants to make your searches as relevant as possible. That's why we offer many ways to help you find the right experiences for you.

On some pages, you can select how to sort the results we display and also use filter options to see only those search results that meet your chosen preferences. You'll see explanations of what those sort options mean when you select them.

If you see a Badge of Excellence label, the award is based on average review ratings, share of bookings with a review, and number of bookings through Cool Destinations over a 12-month period.

The importance of any one factor over any other in a sort order varies, and the balance is constantly being reviewed and adjusted. We're always updating our systems and testing new ways to refine and improve your results to make them as relevant as possible to meet your needs.

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Cool Rewards Terms & Conditions

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Cool Rewards

  • Cool Rewards is a loyalty program operated by Cool Destinations. Rewards may be earned by any eligible person holding a Cool Destinations account, subject to the Cool Destinations customer Terms of Use.

Earning rewards

  • Rewards can be earned by making bookings on the Cool Destinations website. You will be able to see the value of the rewards you can earn during the booking process.
  • Earned rewards will be issued in a pending state and will move to a confirmed state 24 hours after the start time of the experience.
  • Earned rewards will be available to redeem once they are no longer in a pending state.
  • For bookings that are moved to a different travel date, the rewards will be redeemable after the amended travel date.
  • If a booking where rewards were issued is canceled, the earned rewards will not be redeemable and will be moved to a canceled state.

Redeeming rewards

  • To redeem rewards, you must be logged into your Cool Destinations account.
  • Any available rewards will be automatically applied the next time you make a booking, and their value will be deducted from your order at checkout, unless you choose not to apply them, which requires you to indicate this via the toggle switch. Bookings made using rewards are subject to the standard Cool Destinations Customer Terms of Use.
  • You will not be able to redeem only a portion of your available rewards at checkout. It is only possible to redeem all or none of your available rewards.
  • There is no minimum order value required to redeem your rewards. This means that you can pay for 100% of your order with rewards.
  • Rewards are non-transferable and cannot be redeemed for cash.
  • If rewards are redeemed against a booking that is canceled or refunded, the rewards will be reissued to your account.

Miscellaneous

  • You can check your Cool Destinations account to see the rewards you have collected at any time. You are responsible for ensuring that your rewards balance is correct.
  • We reserve the right to modify these Cool Rewards Terms and Conditions at any time, with or without notice, including the rules for earning and redeeming rewards. Any changes will be reflected in the updated Terms and Conditions.
  • We reserve the right to terminate the Cool Rewards program and cease issuing any further rewards on future bookings. All pending and available rewards balances will be honored.
  • By earning and redeeming rewards, you agree to these Terms and Conditions, as well as any subsequent changes made to them.