Chicago Private Sailboat Charter with Captain at Navy Pier
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Experience Chicago from a whole new perspective with the Navy Pier Chicago: Private Sailboat Charter with Captain. Departing from the newly renovated Navy Pier Marina, this all-inclusive VIP sailing adventure offers stunning skyline views and personalized service. Whether you're celebrating a special occasion or just want a relaxing day on the water, this private boat rental delivers a memorable experience.
Enjoy amenities like a spacious open cockpit, a swim platform with a rinse shower, and plenty of floats and noodles for fun in the Chicago Playpen. Bring your favorite snacks and drinks—alcohol is welcome onboard—and listen to your favorite tunes with Bluetooth-connected stereo speakers. The boat features a fully stocked kitchen, a bathroom, and a changing area, making it perfect for a comfortable outing.
With options for groups up to 7 guests, and custom pricing for larger parties up to 12, this private sailing trip offers flexibility and exclusivity. Whether you're cruising past Navy Pier, enjoying a swim, or catching a concert at Northerly Island, this experience puts you right in the heart of Chicago’s vibrant waterfront.
Frequently asked questions
How long is the sailing experience?
The private sailboat charter lasts approximately 3 hours.
What is included in the package?
Your booking includes soda, bottled water, snacks, pool floats, rafts, and towels.
Can I bring my own drinks or food?
Yes, you can bring your own beverages and snacks. Alcohol is allowed onboard.
Is the boat accessible for all ages?
Absolutely. Infants and small children can ride in strollers, and the trip is suitable for all physical fitness levels.
What if I need to cancel?
You can cancel for a full refund at least 24 hours before your scheduled departure. Cancellations within 24 hours are not refundable and may be affected by weather conditions.
Free cancellation
Cancel at least 24 hours before your scheduled departure for a full refund.
Reserve now
Check a date here, then finish booking with our partner. Payment options are confirmed at checkout.
Duration 3 hours
Check availability to see start times.
Live tour guide
English
Key facts
What's included
Included
- Soda/Pop
- Bottled water
- Snacks
- Pool floats, rafts, and towels
Not included
- Additional items available for purchase or BYO
Itinerary
A private 3-hour sailing trip departing from Navy Pier Marina, with options to swim, enjoy Chicago skyline views, and anchor for concerts or relaxing in the water.
Meeting point & pickup
Meet at Navy Pier Marina
All trips start and end at Navy Pier Marina, located at 797 E. Grand Ave., Chicago, IL 60611. The dock is near Gate B or C. The closest parking is the Navy Pier West Parking Garage. For ride shares, the East Parking turnaround is recommended.
Open in Google MapsCancellation & confirmation
Free cancellation
Cancel at least 24 hours before your scheduled departure for a full refund.
- 100% refund if cancelled at least 1 day in advance
- No refund if cancelled within 24 hours or due to bad weather
Instant confirmation
Your booking is confirmed immediately after checkout.
From $1,399.00 per person
- Free cancellation
- Secure checkout with our booking partner
