Private Lake Michigan Sailing Charter and Sightseeing Chicago Skyline Cruise

Imagine gliding across Lake Michigan, with the Chicago skyline stretching out in all its architectural glory just for you. That’s exactly what this private sailing charter offers—a personalized, two-hour adventure that combines relaxation, sightseeing, and a touch of luxury. Whether you’re celebrating a special occasion, seeking a peaceful escape, or simply want a unique perspective of Chicago, this experience promises to deliver.

One of the things we love most about this cruise is its flexibility. Unlike crowded tour boats, this private charter can be tailored to your interests—be it specific landmarks you want to see, preferred routes, or your favorite music. And with a knowledgeable US Coast Guard-licensed captain at the helm, you’re in safe hands while soaking in some of the best panoramic views the city has to offer.

A potential consideration? While the boat offers plenty of space and a relaxing vibe, it’s weather-dependent. If wind conditions aren’t ideal, the route might change, but the captain will keep safety front and center. This tour is best suited for those wanting an intimate, customizable experience on the water—perfect for couples, small groups, or families who appreciate a blend of sightseeing and peaceful sailing.

Key Points

• Private and customizable: You control the route, music, and pace, making for a truly personalized outing.
• Stunning views: See iconic Chicago landmarks and the impressive skyline from the water, offering photo opportunities you won’t find elsewhere.
• Expert guidance: The captain is licensed by the US Coast Guard and is happy to serve as tour guide or simply follow your lead.
• Flexible itinerary: Wind and weather influence the route, but the captain is happy to accommodate your preferences.
• Value for money: For $49, you get approximately 2 hours of private sailing, including a knowledgeable captain and Bluetooth speakers.
• No food or drinks included: Travelers should plan to bring their own beverages, as the tour doesn’t cover catering or alcohol.

An Authentic Look at the Experience

This private Chicago sailing cruise offers an escape from the hustle, giving you a peaceful two-and-a-half hours floating along Lake Michigan’s calm waters. The departure point, Come Sailing, is conveniently located on the north side of Monroe Harbor, with easy access via public transportation and a dedicated pickup spot.

The actual experience begins with a safety briefing—nothing too formal, just enough to set everyone at ease. Once aboard, the boat’s relaxed atmosphere sets the tone. The captain, whose expertise is evident, will navigate based on wind and weather, but the real charm lies in your ability to direct the route if desired. Want to pass by Navy Pier or get a close-up view of Soldier Field? Just ask.

Detailed Stop-by-Stop Breakdown

Stop 1: Monroe Harbor Departure
Your journey begins here, with the captain preparing the boat and giving a quick safety rundown. We loved how laid-back and friendly the crew was—nothing stuffy about this trip. The boat itself is equipped with Bluetooth speakers, so you can set your playlist and truly make the experience your own.

Stop 2: Buckingham Fountain
As the sail kicks off with a gentle motor through Monroe Harbor, you’ll get a fantastic view of the world-famous Buckingham Fountain. Not only is this one of the largest fountains globally, but it also played a role in Chicago’s royal history, having hosted Queen Elizabeth II in 1959. The surrounding Grant Park adds to the photo-worthy scenery. It’s worth noting that from the water, you get a unique perspective—most visitors only see it from land.

Stop 3: Adler Planetarium
Looking at the dome of the Adler Planetarium from the lakeside offers a fresh angle on this iconic Chicago landmark. Built in 1930, it’s nestled on Northerly Island and features the Doane Observatory with a large telescope, which might not be visible from the boat but can be appreciated from this unique vantage point. It’s a favorite among couples looking for a picturesque backdrop for photos.

Stop 4: Soldier Field
The historic colonnades of Soldier Field are visible from the water, echoing their 1924 origins. Home to the Chicago Bears today, this stadium has hosted all kinds of memorable events, and sailing past it offers a subtle reminder of Chicago’s sports and entertainment history.

Stop 5: Navy Pier
One of Chicago’s most recognizable landmarks, Navy Pier is a hub of activity and history. From the water, you can admire the Grand Ballroom and the pier’s impressive architecture, which has played a vital role since 1916. This stop also offers a chance for some great photos, especially of the colorful buildings and bustling atmosphere.

Stop 6: Chicago Skyline
Of course, no trip like this would be complete without a view of the skyline. From the water, the city’s tall towers, including iconic structures like the Willis Tower and John Hancock Center, seem even more dramatic. It’s a visual feast and a favorite feature for many travelers, with the flexibility to linger or move along depending on your mood.

What Makes This Tour Stand Out?

We appreciated how personal this experience feels. Unlike crowded boat tours, this private sail allows for a more relaxed, intimate atmosphere. The captain’s willingness to customize the route and playlist means you can truly make the trip your own, whether you want a romantic ride with soft music or an energetic sightseeing tour.

The inclusion of Bluetooth speakers was a thoughtful touch, letting you control the background music—perfect for setting the mood or enjoying your favorite tunes while taking in the sights. The captain’s friendly, knowledgeable approach adds a layer of comfort, and reviewers have noted how engaging and helpful he was, even sharing insights about Chicago’s landmarks.

One reviewer, Giulliana, commented, “Great experience super relaxing and wonderful sights. Loved the privacy, I did great with my dramamine and bracelets so no sea sickness it was a cool way to see the city.” This highlights how the tour can be tailored for comfort—a big plus if you’re prone to seasickness or just prefer a relaxed pace.

Pricing and Value

At $49 per person, this cruise offers impressive value. It’s a short but sweet experience—two hours that are packed with sights, personalized service, and tranquility. For those seeking a different perspective of Chicago—away from busy land-based tours—this private sailing is a worthwhile splurge.

While food and drinks aren’t included, the boat provides a small cooler for your beverages, and you’re encouraged to bring your own. The option to bring alcohol (within Illinois law) adds to the relaxed vibe. Keep in mind, this isn’t a party boat; it’s a peaceful, scenic ride meant to be enjoyed at your own pace.

Practical Details

The tour departs from Come Sailing on the north side of Monroe Harbor. The meeting point is accessible via public transportation, making it easy to reach without the hassle of parking. The boat is designed for small groups—up to four people—which makes it ideal for intimate gatherings or small families.

The experience lasts approximately 2 hours, and the itinerary is weather-dependent. If wind conditions aren’t ideal, the captain will adjust the route to ensure safety and maximum enjoyment. The tour is non-smoking, and alcohol is permitted within limits, but swimming isn’t allowed.

COVID-19 precautions include optional masks, social distancing within your group, and guidelines for health and safety. The boat has small restrooms, but these are best used sparingly, and the crew encourages using shore facilities if needed.

Who Would Love This Tour?

This sail is perfect for romantic couples seeking a private, scenic escape. It’s also well-suited for small groups of friends wanting a relaxed, customizable day on the water. If you’re someone who appreciates stunning city views from a peaceful setting and enjoys a personal touch, this cruise hits the mark.

It’s not designed for those looking for a boisterous party or a long sightseeing extravaganza—think of it as a cozy, intimate way to see Chicago from its best angle, the water.

The Sum Up

This private Lake Michigan sailing cruise offers an authentic, peaceful way to experience Chicago’s iconic skyline and lakeside landmarks. For a modest price, you get a flexible, intimate adventure led by a friendly, knowledgeable captain who’s eager to customize your journey. The scenic views, combined with the option to control the route and music, make this a unique and memorable outing.

It’s especially ideal for couples, small groups, or anyone craving a quiet, scenic escape with personalized service. While weather can influence the route, the overall experience remains a tranquil, beautiful way to see the city from a fresh perspective.

If you value privacy, flexibility, and stunning scenery, this sailing trip is worth considering. It’s a wonderful alternative to crowded boat tours, turning a simple cruise into a tailored adventure—perfect for creating lasting memories of Chicago from its scenic waterway.

FAQ

How long is the cruise?
The cruise lasts approximately 2 hours, offering plenty of time to relax and enjoy the sights without feeling rushed.

Where does the tour depart from?
It departs from Come Sailing, located on the north side of Monroe Harbor at 801 E Grand Ave in Chicago.

Can I customize the route?
Yes, the trip is private and flexible. You can choose to see specific landmarks or leave it up to the captain, based on wind and weather conditions.

Is food or drinks included?
No, food and drinks are not included. However, you can bring your own beverages and store them in the provided cooler.

Are there any age or group size restrictions?
The tour is designed for groups of up to four people, making it ideal for small gatherings or couples.

Is the experience suitable for people with seasickness?
Many reviewers have managed seasickness well, especially with precautions like bracelets. The trip is generally smooth, but it’s best to bring remedies if you’re prone to seasickness.

What should I wear?
Dress comfortably for the weather, and bring layers if needed. It’s a boat, so wind and spray can be factors, even on a calm day.

What happens if the weather turns bad?
The captain monitors conditions and may reschedule or cancel for safety reasons. In such cases, a full refund or date change will be offered.

Whether you’re after a peaceful, scenic cruise or a customizable private outing, this sailing adventure offers a refreshing way to see Chicago from a different angle—relaxing, personal, and full of stunning views.