Private Chicago Sunset Sailing Charter on Lake Michigan

3 hours (approximately)
Offered in: English

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.

What's Included

Private Sailing Charter
Captain Included
Life Jackets Onboard
Gratuity for Captain and Crew

Meeting and pickup

Meeting point

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.

End point
This activity ends back at the meeting point.

Itinerary

Duration: 3 hours (approximately)
  • 1
    Chicago Skyline

    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.

    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
Supplied by Two Brothers Sailing Adventures

Tags

Day Cruises
Sailing
Nature and Wildlife Tours
Extreme Sports
Half-day Tours
Private and Luxury
Romantic Tours
Private Sightseeing Tours
Sunset Cruises
Photography Tours
Cultural Tours
Historical Tours
Safaris
Ports of Call Tours
City Tours
Water Tours
Sightseeing Cruises
Shore Excursions
Food & Drink
Adventure Tours
Involves Animals

Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

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