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Enjoy a private sunset sail on Lake Michigan from Navy Pier, Chicago, with personalized routes, stunning city views, and the chance to bring your own drinks for a relaxing 2-hour experience.

The Serene Private Sunset Sail offers an exclusive way to experience Chicago’s iconic skyline and Lake Michigan. For $507.96 per group (up to 6 people), this 2-hour tour combines the tranquility of sailing with personalized touches that make each trip unique. Departing from Navy Pier, the tour is led by a US Coast Guard-certified captain, ensuring safety and expert guidance. The trip is highly recommended, with a perfect 5.0-star rating based on 27 reviews, and booked on average 46 days in advance.
This private sailing experience emphasizes customization: travelers can select their route, play their favorite music using Bluetooth speakers, and bring their own drinks and snacks to enjoy on board. The tour is ideal for those seeking a peaceful, scenic escape on Lake Michigan, with the flexibility to tailor the voyage to personal preferences.

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The tour begins at Navy Pier Marina, a well-known Chicago landmark and popular tourist destination. The departure point is clearly marked at 801 E Grand Ave, and the experience includes a safety briefing before setting sail. The proximity to public transportation makes it accessible for visitors, and the Navy Pier Facility Fee is included in the price.
The pier offers excellent views of Navy Pier itself, along with the eastern end of the Chicago skyline. The location provides a picturesque setting for beginning your sunset sail and ensures easy access to the boat after a brief safety introduction.
An outstanding feature of this tour is the ability to choose your route. This allows guests to focus on different sights along Lake Michigan depending on their interests. Whether it’s passing the Adler Planetarium on the northeast corner of Northerly Island or catching a glimpse of Soldier Field, the sail takes you past some of Chicago’s most recognizable waterfront landmarks.
Each trip is tailored to the group’s preferences, making each journey truly unique. The captain’s expertise ensures a smooth and safe sail whether you prefer a relaxed cruise or a route that emphasizes particular sights.

Sailing past Navy Pier, travelers enjoy spectacular views of the Grand Ballroom, the Ferris Wheel, and the bustling activity along the shoreline. The scenic waterway offers an entirely different perspective of this lively area.
As the boat moves into Lake Michigan, the Chicago skyline becomes the main focus. The water-based vantage point reveals details about the city’s architecture and landmarks that are often missed from land. The sail provides ample opportunities for photos and quiet reflection while soaking up the breathtaking cityscape.

Chicago’s skyline is renowned for its diverse architecture and distinctive skyscrapers. From the water, the views are especially striking, allowing for an appreciation of the city’s urban design. The sail passes by notable structures like the Adler Planetarium and Soldier Field, providing a visual story of Chicago’s waterfront development.
Travelers report that the water perspective enhances their understanding of Chicago’s architectural history and the story behind its skyline. The experience is perfect for architecture enthusiasts or anyone eager to see the city from a unique vantage point.
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The main highlight of this tour is the sunset experience. As the boat approaches the twilight hours, the city lights begin to glow, and the sky turns vibrant with rich colors. Watching Chicago’s skyline light up from the water creates a serene and memorable atmosphere.
Several reviews mention the gorgeous sunset combined with the progression into night, offering the chance to see the city in both daylight and illuminated splendor. The tour ends back at Navy Pier, often with guests lingering to take in the post-sunset glow.

Unlike many group tours, this sailing experience encourages guests to bring their own drinks and snacks. The vessel is equipped with a refrigerator and ice, making it easy to keep beverages cool. The ability to customize your onboard refreshments adds a relaxed, personal touch to the experience.
The tour explicitly states that alcohol can be consumed within Illinois law, but glass containers are prohibited. Plastic cups are recommended for safety and convenience. This setup makes it ideal for celebrating birthdays, romantic dates, or simply enjoying a quiet evening with friends and family.

To enhance the experience, travelers are advised to arrive on time, as late arrivals may lead to a shortened cruise without refund. Since swimming is not permitted and seasickness can occur, guests should be prepared accordingly. Seasickness sufferers are recommended to stay on deck during rougher waters.
The vessel is non-smoking and no animals are allowed, ensuring a clean and comfortable environment for all onboard. The capable crew also emphasizes respectful behavior, with inappropriate conduct leading to early termination of the trip.
This tour is subject to weather conditions. If the sailing is canceled due to poor weather, guests are offered to reschedule or receive a full refund. The free cancellation policy allows full refunds if canceled more than 24 hours in advance, providing peace of mind for planning.
The captain reserves the right to cancel at any time if safety is a concern, and rescheduling is facilitated to ensure flexibility.
The Come Sailing team manages this private sailing experience. Known for their professionalism and safety standards, they also facilitate a highly personalized and relaxed environment. Their knowledgeable captain has earned praise for making each trip enjoyable and safe.
The company ensures a smooth booking process, with confirmation received immediately upon booking and clear instructions on the departure point. They also maintain high standards for behavior and safety, including strict no-smoking policies and rules about alcohol and glass containers.
This private, customizable sail offers a unique way to see Chicago’s skyline from Lake Michigan. The 2-hour trip balances scenic views, relaxation, and personal touches like the ability to bring your own drinks and music. It suits small groups, families, or couples looking for a peaceful yet memorable experience.
While parking is not included and additional expenses like food or drinks are up to guests, the overall value lies in the privacy, flexibility, and stunning vistas. The highly positive reviews confirm that most find the experience gorgeous and worthwhile, especially for celebrating special moments or simply enjoying a quiet evening on the water.
This tour is best for those who value personalized experiences, beautiful sunsets, and Chicago’s waterfront from a comfortable boat with expert guidance. It’s an elegant way to unwind and take in the city’s iconic beauty in a serene setting.
“A fantastic experience – beautiful weather and relaxing atmosphere. Will definitely try again and recommend to others”
Can I bring my own drinks?
Yes, guests are encouraged to bring their own drinks and snacks, and the boat is equipped with a refrigerator and ice to keep beverages cool.
Is this tour suitable for children?
Most travelers can participate, but children must remain on deck during the sail, as swimming is not allowed and below-deck areas are off-limits.
What is included in the price?
The professional US Coast Guard-licensed captain, all taxes, Bluetooth speakers, and the Navy Pier Facility Fee are included. Food and drinks are not, but you may bring your own.
What happens if the weather is bad?
The tour is weather-dependent. If canceled due to poor weather, guests are offered rebooking options or a full refund.
How far in advance should I book?
Most bookings are made about 46 days in advance, but availability varies.
Are animals allowed onboard?
No, animals are not permitted on this sailing experience.