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Duration: 1 hour and 15 minutes

Overview

Set sail on Lake Michigan with the Chicago Tall Ship Skyline Sail and witness the Windy City's skyline from an unforgettable vantage point. Choose from themed sails like maritime stories, architecture tours, happy hour, or sunset views for a unique 75-minute journey that's perfect for any occasion.

🌆 Experience the iconic Chicago skyline from the unique perspective of Lake Michigan

🏴‍☠️ Dive into maritime stories or architectural wonders on specialized sails

🍹 Enjoy a 'Happy Arr-our' or serene sunset with themed drinks available

📸 Capture breathtaking photos of Chicago’s famous landmarks from the water

Availability

When do I choose a date?

After purchase, you can request your preferred dates and times by following the instructions in the email you receive. If it's a gift, the recipient will also get an email with booking instructions.

Seasonal,
May - October 1st:
Daily 1:00pm, 3:00pm, 5:00pm or 7:00pm

Full description

Escape the concrete jungle and set sail on Lake Michigan for a refreshing 75-minute voyage with Chicago's Tall Ship Skyline Sail. It's your ticket to the ultimate chill-out session, gliding past the iconic skyline that makes the Windy City oh-so-photogenic. Whether you're a history buff ready to dive into pirates and maritime tales at 1 pm or an architecture aficionado eager for the 3 pm skyline tour, there's a sail with your name on it. Fancy a tipple with a view? The 5 pm Happy Arr-our has you covered, or maybe it's the magic of the golden hour you're after during the 7 pm sunset sail. And don't forget, from September 3, the sunset gets even sweeter with a Twilight Sail. It's the perfect blend of relaxation and discovery, all while basking in the beauty of Chicago from a perspective not many get to see. So why wait? Click through, pick your sail, and let the adventures begin!

Practical information

Any restrictions to participate?

  • Age: All age groups are welcome.
  • Physical limitations: Must be able to board and disembark the ship with minimal assistance.
  • Experience level: Suitable for beginners; no prior sailing experience required.

Who can you accommodate for?

  • Children: Children of all ages are welcome but must be supervised by an adult.
  • Individuals with disabilities: Please contact us in advance to discuss specific needs and accommodations.
  • Pets: Unfortunately, pets are not allowed onboard for safety reasons.

What to expect on the day of the experience?

  • Duration: Each sail is approximately 75 minutes long.
  • What’s included: A scenic sail around Lake Michigan with various themes depending on the time of day.
  • Who will be present: A skilled sailing crew and a guide for thematic sails.
  • Photo/ video: Guests are encouraged to take photos and videos to remember their experience. Professional photography may also be available.
  • Specific rules to follow: Safety instructions provided by the crew must be followed at all times. Smoking is not allowed on the ship.

How to prepare?

  • Weather dependency: Sails are weather-dependent; check in advance for any weather-related changes to your booking.
  • Arrival: Plan to arrive at least 30 minutes in advance of your sail time to check in.
  • Parking: Available at Navy Pier; see the detailed directions provided for the best parking options.
  • What to wear: Dress for the weather with comfortable shoes. Layers are recommended as it can be cooler on the water.
  • What to bring: Sun protection, water, and any personal items you might need. Remember, space on the ship is limited.
  • Restrooms/ lockers/ changing rooms: Available at Navy Pier but not on the ship. Plan accordingly.

Returns, exchanges and cancellation

Unused Experience Vouchers can be returned within 30 days for a full refund to the original purchaser, no questions asked.

If you have any unused Experience Vouchers, you can exchange them for anything else in our marketplace, no matter when. If you choose an experience that's more expensive, you'll need to pay the difference, but if you choose one that costs less, you'll receive a credit towards your next booking.

No refunds are allowed once the experience is booked, but you can reschedule up to 48 hours before your experience, for a date within a year of the original booking. To reschedule, contact the experience provider directly. No-shows or rescheduling less than 48 hours in advance means losing the value of your experience.

Duration: 1 hour and 15 minutes
Regular price $55
$55 Regular price $59 Sale price
You save $4

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Here's what others have to say!

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Daniel M.

Gliding past Chicago's skyline on a tall ship offered a refreshing escape, blending historical insights and scenic beauty into a perfect outing.

Matthew O.

The fireworks sail provided an unmatched viewing experience, combining the tranquility of Lake Michigan with the spectacle of Chicago's night sky.

Sophia N.

The blues concert sail turned a mundane Monday into an extraordinary evening of music and skyline views, offering a unique blend of entertainment on the water.