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Two people on a boat with a clear sky and water in the background. 1
A group of people on a sailboat with a city skyline in the background. 2
A person holding a rope on a boat with a city skyline in the background. 3
A sailboat with people on deck, a city skyline in the background, and calm waters. 4
A person sailing on a sailboat with a clear sky and calm sea. 5

Private Chicago Sunset Sailing Charter on Lake Michigan

By Two Brothers Sailing Adventures
Free cancellation available
Price is P 81,794 per traveler* *Get a lower price by selecting multiple travelers
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Features

  • Free cancellation available
  • 3h
  • Mobile voucher
  • Instant confirmation

Overview

Enjoy a serene evening on Lake Michigan with a private sunset sailing charter, where the stunning Chicago skyline transforms as the sun sets. Departing from Montrose Harbor, this exclusive experience offers a cozy atmosphere for date nights, anniversaries, and memorable celebrations. Aboard the Vagabond, a Beneteau Oceanis 393 yacht, guests can unwind, capture picturesque moments, and savor their favorite BYOB drinks and snacks against the backdrop of golden-hour light. With a dedicated captain overseeing your journey, relish a tranquil escape just minutes from the bustling city.

Activity location

  • Chicago Skyline
    • 60601, Chicago, Illinois, United States

Meeting/Redemption Point

  • 344 W Montrose Harbor Dr
    • 344 West Montrose Harbor Drive
    • 60640, Chicago, Illinois, United States

Check availability

Private Chicago Sunset Sailing Charter on Lake Michigan

  • Activity duration is 3 hours3h
    3h
  • English
Language options: English
Starting time: 18:00
Price details
P 81,793.80 x 1 TravelerP 81,793.80
Total
Price is P 81,793.80

What's included, what's not

  • What's includedWhat's included
    Private Sailing Charter
  • What's includedWhat's included
    Captain Included
  • What's includedWhat's included
    Life Jackets Onboard
  • What's excludedWhat's excluded
    Gratuity for Captain and Crew

Know before you book

  • Public transportation options are available nearby
  • Infants are required to sit on an adult’s lap
  • Suitable for all physical fitness levels

Activity itinerary

Chicago Skyline

  • 3h
Guests board a private sailboat at Montrose Harbor and sail onto Lake Michigan for a scenic Chicago sunset experience. After a brief welcome and safety overview from the captain and crew, relax on deck, take photos, enjoy the lake breeze, and watch the city begin to glow as the sun sets over the skyline. Depending on wind, weather, and lake conditions, the route may include views toward downtown Chicago, nearby beaches, Navy Pier, the Playpen, and other scenic lakefront landmarks. This private sunset sailing experience is ideal for couples, date nights, anniversaries, proposals, birthdays, visitors, and small group celebrations. It offers a peaceful, romantic, and personal way to experience Chicago from the water during one of the most beautiful times of day.

Location

Activity location

  • LOB_ACTIVITIESLOB_ACTIVITIES
    Chicago Skyline
    • 60601, Chicago, Illinois, United States

Meeting/Redemption Point

  • PEOPLEPEOPLE
    344 W Montrose Harbor Dr
    • 344 West Montrose Harbor Drive
    • 60640, Chicago, Illinois, United States

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