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Offered languages
- English
A private sailing charter on Lake Michigan offers a serene escape with stunning skyline views of Chicago. Departing from Montrose Harbor, enjoy a relaxed atmosphere ideal for families, couples, or casual groups looking for a break from city life. Experience the charm of a personal sailing trip as you glide across the water, capturing perfect moments of the skyline from your private vessel. This charter caters to visitors and locals alike, providing a unique perspective of the city while ensuring a peaceful outing on the lake.
- Private sailboat reserved exclusively for your group
- BYOB-friendly with restroom and cooler space onboard
- Scenic views of the Chicago skyline and lakefront
- Ideal for families, groups, couples, and first-time sailors
What's Included
Meeting and pickup
Meet at Dock F inside Montrose Harbor. Please arrive early and look for the Dock F entrance/gate near the harbor docks. Your captain or crew member will meet you there and help guide you to the boat. If you have trouble finding the dock, call or text us and we’ll help direct you.
Itinerary
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1Chicago Skyline
Guests will board a private sailboat at Montrose Harbor and head out onto Lake Michigan for a scenic Chicago sailing experience. After a brief welcome and safety overview from the captain and crew, the boat will leave the harbor and sail along the Chicago lakefront. From the water, travelers can enjoy wide-open views of Lake Michigan, the Chicago skyline, nearby beaches, and the city’s north lakefront. Depending on wind, weather, and lake conditions, the route may include views toward downtown Chicago, Navy Pier, the Playpen area, and other scenic lakefront landmarks. During the cruise, guests can relax on deck, take photos, enjoy snacks and drinks they bring aboard, feel the lake breeze, and experience Chicago from one of its best viewpoints: the water. This is a private, relaxed sailing experience rather than a crowded tour boat, making it ideal for couples, families, friends, birthdays, visitors, and small group celebrations.
3 hours • Admission ticket free
Additional info
- Public transportation options are available nearby
- Infants are required to sit on an adult’s lap
- Suitable for all physical fitness levels
Tags
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
Cancellation Policy
- For a full refund, you must cancel at least 24 hours before the experience’s start time.
- If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.
- Any changes made less than 24 hours before the experience’s start time will not be accepted.
- This experience requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.
You can cancel up to 24 hours in advance of the experience for a full refund.
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