Private Sailing on Beautiful Lake Michigan – Navy Pier, Chicago

Chicago’s skyline from Lake Michigan: a perspective few get to enjoy. For those seeking a truly unique way to see this vibrant city, a private sailing trip from Navy Pier offers an intimate, picturesque escape on the water. Priced at around $567 for a group of up to six, this two-hour adventure is led by a licensed captain and promises a personalized experience—whether you want to simply relax, learn about sailing, or snap spectacular photos of Chicago’s architecture.

What we love most about this experience is how customizable it is—you can tailor the route to focus on your favorite sights, and with Bluetooth speakers onboard, you can set your own soundtrack as you cruise. Plus, the boat is kept pristine and comfortable, making it suitable even for those new to sailing. The only thing to consider is that food and drinks are not included, so you might want to bring your own snacks or beverages.

This tour is perfect for anyone celebrating a special occasion, from birthdays to anniversaries, or just travelers wanting a quiet, private break from tourist crowds. It’s also highly praised for knowledgeable guides and stunning views, making it a memorable highlight of a Chicago trip.

Key Points

• Private, customizable experience tailored to your interests.
• Spectacular views of Chicago’s skyline and landmarks from Lake Michigan.
• Expert, friendly captains who can answer questions and even let you steer.
• Flexible start times to fit your schedule.
• Includes Bluetooth speakers, making your trip personalized with your favorite music.
• Great for special occasions or quiet escapes from the busy city.

A Close-Up Look at the Private Lake Michigan Sailing Tour

When we consider what makes a memorable city experience, it’s often about seeing iconic sights from a fresh perspective. This private sailing tour from Navy Pier offers just that—a chance to view Chicago’s stunning skyline and waterfront landmarks up close and personal. Think of the experience as a floating window into the city’s scenic beauty, away from the crowds and noise of busy streets.

The departure point is Navy Pier Marina, a well-known Chicago landmark and a hub for water-based activities. After a brief safety briefing—something we found reassuring—the boat is set for your adventure. The boat itself is spotlessly clean and comfortable, with space for up to six guests, making it perfect for family groups, friends, or couples seeking an exclusive outing.

Captain Mike or Ulysses (both highly praised in reviews) are your guides on this journey. Their knowledge about sailing, Chicago’s history, and the local sights helps turn a simple boat ride into an engaging and educational experience. Many reviewers mention how Captain Mike answered all sorts of questions, sharing stories about the city and its architecture, which added a personal touch to the trip.

What’s Included and What to Expect

For the price of around $566, you get the entire boat for your party, a licensed captain, and the use of Bluetooth speakers—allowing you to enjoy your playlist as you cruise. All taxes and the Navy Pier facility fee are included, removing surprises on the billing end. You’ll also receive a brief safety orientation, which we appreciated for peace of mind.

You might wonder about the itinerary—it’s fully customizable. Typical stops include passing Navy Pier itself, which offers fantastic views of the Grand Ballroom and the bustling lakefront. As you sail east, you’ll admire Chicago’s dramatic skyline—a collection of architectural marvels that look even more impressive from the water.

Other highlights include passing by the Adler Planetarium—an iconic dome on Northerly Island—and getting a clear view of Soldier Field, home of the Chicago Bears. As one reviewer put it, “The views of the city from the lake are unlike anything you see from streets or rooftops.”

Authentic Experiences and Highlights from Guest Reviews

Reviewers consistently praise the knowledgeable and friendly guides. “Captain Mike was awesome,” one describes, “answering all kinds of questions about sailing and Chicago history,” which adds depth to the experience. The personal touch makes this feel less like a tour and more like a day out with friends.

Many guests mention the stunning views of Chicago’s architecture, especially the skyline and waterfront landmarks. “The views of downtown from the water are spectacular,” a traveler notes, and several say they could have happily gone all day—“I wish it was longer,” was a recurring theme.

Music and ambiance are also highlights. With Bluetooth-enabled speakers, you can set your favorite tunes, making the trip feel even more relaxed and tailored. As one guest noted, “We loved the way the music added to the vibe, and it was such a peaceful way to enjoy the city.”

The Itinerary in Detail

While flexible, the typical route offers a series of highlights. Starting at Navy Pier Marina, the boat departs on the north side of Navy Pier, famous for its attractions and lively atmosphere. From there, the boat glides past the pier, giving you a chance to see the grand architecture and bustling activity from the water.

Moving eastward, you’ll see the majestic Chicago skyline—a true feast for photographers. Many rave about the up-close view of iconic buildings like the Willis Tower and John Hancock Center, which look even more impressive from the water.

Further along, the boat passes by the Adler Planetarium—a distinctive dome-shaped building that’s been a Chicago fixture since 1930. The proximity gives a great photo opportunity, especially as the boat cruises around Northerly Island.

As you approach Soldier Field, the view of the historic stadium—a modern icon with a storied past—is striking. The area is rich with stories, and your captain can share a few tidbits that make the experience more meaningful.

Depending on your interests, the captain can adjust course, perhaps heading toward Monroe Harbor for a glimpse of the Queen Elizabeth II’s historic visit in 1959 or simply cruising the shoreline to soak in the cityscape.

Authenticity and Comfort: What makes this trip special?

Guests repeatedly mention the cleanliness and comfort of the boat. It’s well-maintained, and given the reviews like “the boat was beautiful and very clean,” you know you’re in good hands. The boat’s size makes it intimate yet spacious enough to relax and enjoy the scenery.

The professionalism of the captain is another highlight. “Captain Ulysses was a wonderful guide—friendly, knowledgeable, and attentive,” one review states. Knowing you’re with a licensed captain who is attentive enhances the safety and enjoyment of the trip.

Price and Value: Is it worth it?

At around $566 for six people, this experience offers good value, especially considering it’s entirely private. Compared to crowded boat tours or expensive rooftop bars, you’re getting a personalized, flexible experience with your own crew. The inclusion of a captain, music, taxes, and facility fees simplifies budgeting, too.

The reviews reinforce that guests feel they received good value, with many saying they would gladly pay for this experience again. Several mention that it was the perfect way to celebrate special occasions like birthdays or anniversaries, emphasizing its suitability for memorable moments.

Practical Considerations

While most travelers find it straightforward, keep in mind that food and drinks are not included, so plan to bring your own snacks or beverages. Glass containers are prohibited, but bottles in protective containers are allowed—bring plastic cups for easy sipping.

Weather plays a role: the captain reserves the right to cancel for safety reasons, and rescheduling is usually flexible. This makes it wise to book with some flexibility in mind. The boat is not suitable for smoking or animals, so plan accordingly.

Finally, punctuality matters—late arrivals may result in shortened trips without refunds, so setting a timely departure is key to making the most of your two hours.

Who Should Consider This Experience?

This sailing tour is ideal for small groups seeking a private, relaxed adventure on Lake Michigan. It’s perfect for romantic getaways, celebrations, or small family outings. If you’re interested in Chicago’s architecture, skyline views, and the lake’s tranquility, this tour offers a distinctive perspective. It’s also well-suited for those who enjoy personalized service and a flexible schedule.

Travelers who love learning about local history or sailing might find this especially engaging, while anyone wanting a peaceful escape from the city’s hustle will appreciate the calm waters and intimate setting.

The Sum Up

A private sailing trip on Lake Michigan from Navy Pier provides a quintessential Chicago experience—the city’s famous skyline, historic landmarks, and shimmering water all in one relaxing outing. With friendly, knowledgeable guides and customizable routes, it’s a genuinely personal way to connect with the city’s waterfront.

Whether celebrating a special day, seeking a peaceful retreat, or simply wanting a different view of Chicago, this experience offers great value and memorable moments. The small group size, intimate setting, and scenic backdrop make it a must-try for travelers who appreciate a mix of adventure, culture, and comfort.

If you’re after a peaceful, visually stunning, and personalized way to see Chicago from the water, this private sailing tour might just be the highlight of your trip.

FAQ

How long is the sailing trip?
The tour lasts approximately 2 hours, giving you plenty of time to relax, take photos, and enjoy the scenery without feeling rushed.

What is included in the price?
Your group will have the exclusive use of the boat, a US Coast Guard licensed captain, and Bluetooth speakers to play your music. Taxes and the Navy Pier facility fee are also covered.

Can I bring food and drinks?
Yes, you can bring reasonable amounts of food and beverages, but glass containers are not allowed. Bring plastic cups for easy drinking onboard.

Is the trip suitable for children?
Most travelers can participate, but it’s best to keep children supervised and be aware that smoking and animals are prohibited.

What happens if the weather is bad?
The captain has the right to cancel the trip for safety reasons. If canceled due to weather, you’ll be offered a rebooking or full refund.

Can I get a refund if I cancel?
Yes, you can cancel up to 24 hours in advance for a full refund. Cancellations within 24 hours won’t be refunded.

Is parking available?
Parking is not included in the price, so plan ahead. Navy Pier has parking options, but they can fill up quickly during busy times.

Can I steer the boat?
You’re welcome to take a turn at the helm if the captain permits, which many guests find fun and educational.

In all, this private sailing trip balances personalized service, stunning visuals, and comfort. It’s an excellent choice for those wanting to see Chicago from a different angle—calm, intimate, and full of memorable sights.