Private Sailing on Beautiful Lake Michigan – Navy Pier, Chicago

Imagine gliding across Lake Michigan, your eyes taking in the iconic Chicago skyline from a perspective few visitors get to see. That’s exactly what this private sailing tour offers—an intimate, customizable adventure on the water that’s perfect for celebrating a special occasion or simply treating yourself to a different view of the city. It’s a chance to escape the crowds and soak in the city’s beauty at your own pace.

What makes this experience stand out? First, the personalized nature of the trip, with itineraries tailored to your group’s interests and the option to take the helm yourself. Second, the stunning views of Chicago’s architecture and landmarks from a peaceful vantage point. The only potential drawback? Since it’s weather-dependent, a good day is essential—bad weather means rescheduling or a full refund. This tour suits those who appreciate quiet moments on the water, want a private experience, or are celebrating something special.

Key Points

• Fully customizable itineraries allow you to focus on what interests you most
• Exclusivity with private use of a sailboat, perfect for small groups
• Spectacular views of Chicago’s skyline, Navy Pier, and iconic landmarks
• Knowledgeable captain who shares stories and answers questions
• Flexible start times to suit your schedule
• Includes Bluetooth speakers for personalized music on the water

An Overview of the Experience

This private sail on Lake Michigan lasts around two hours—enough time to relax, take photos, and enjoy the peacefulness of the lake without feeling rushed. Departure is from Navy Pier Marina, a lively hub that’s easily accessible and a tourist favorite. The trip begins after a quick safety briefing, and then you’re whisked away into a world of sparkling waters and city views.

The boat itself is well-maintained, clean, and designed for comfort. The professional US Coast Guard-licensed captain is the highlight, offering insights on sailing, Chicago history, and interesting tidbits about the sights you pass. Many reviews rave about Captain Mike and Captain Ulysses, who are described as knowledgeable, friendly, and attentive—making the journey not just beautiful but also informative.

Breaking Down the Itinerary

Start at Navy Pier Marina

Navy Pier is Chicago’s most recognizable waterfront landmark, bustling with activity and offering a perfect starting point. As you cast off, you’ll immediately see the city’s skyline open up in front of you. From the water, the architecture and engineering marvels of Chicago become even more impressive, with stories hidden behind every building.

Passing the East End of Navy Pier

Sailing past this iconic spot gives you a view of the Ferris wheel, the Centennial Wheel, and the lively crowds below. Many guests appreciate how different it feels to see this lively hub from the quiet of a boat, giving you an almost secret glimpse.

Chicago Skyline Views

From the water, you’ll see the city’s impressive skyline—neighborhoods like the Loop and the Gold Coast from a fresh perspective. The views are especially striking with the city’s architecture lit up at sunset or during the day when the skyscrapers shine brightly against the lake.

Iconic Landmarks

A highlight is passing by the Adler Planetarium on Northerly Island, built in 1930. The dome is striking from the boat, and many mention their fascination with the way the city and water frame this historic structure.

Soldier Field, home of the Chicago Bears, is another memorable sight. Built in 1924, it’s a stadium with a storied past, its silhouette clear from the lake. Many reviews note how it has changed over the years but remains a significant Chicago landmark.

A Royal Visit and Other Stories

One fun historical tidbit involves Queen Elizabeth II’s visit in 1959, when her barge was ferried from Monroe Harbor to Queens Landing. Such stories add a layer of charm and context that captains are happy to share.

What to Expect on the Boat

The vessel is designed for comfort, with space to spread out and enjoy the scenery. The tour includes Bluetooth-enabled speakers, allowing you to play your favorite tunes while taking in the views. Many guests mention how the music adds a personalized touch, making the experience feel even more relaxed.

You’re encouraged to bring drinks, and alcohol is permitted within Illinois law, but glass is not allowed on board. Many reviews highlight how the experience is perfect for celebrating birthdays, anniversaries, or just a relaxing day out with friends. The boat is private for your group of up to six, making it an intimate alternative to crowded tours.

Captain Mike and others are praised for their responsiveness—they answer questions about sailing, Chicago’s history, and the sights. The captain’s knowledge makes the ride not just scenic but also educational, especially if you’re interested in architecture or local stories.

Additional Details and Practicalities

The tour costs about $566.82 per group, which includes all taxes, the Navy Pier Facility Fee, and the use of the boat and captain. While this may seem steep at first glance, the exclusivity and personalized experience provide good value, especially for celebrating a special occasion or enjoying a unique outing with friends or family.

Timing options are flexible, with several start times to fit your schedule. The tour is suitable for most travelers, but keep in mind it’s weather-dependent, and sea or weather conditions could lead to rescheduling. It’s a fully private experience, so you’re not sharing the boat with strangers, which many reviews find particularly appealing.

Parking at Navy Pier can be tricky and costly, so plan ahead or consider public transit. Also, note the policies on smoking, glass containers, and behavior—professionalism and safety are emphasized, which keeps the experience enjoyable for everyone.

Why This Experience Is Worth It

The standout feature here is the combination of privacy, customization, and scenic beauty. You’re not just a passenger; you can influence the route and even try sailing yourself if you’re interested. Many guests cite the friendly, knowledgeable captains and the stunning city views as the best parts of their trip.

The reviews consistently praise the excellent customer service and the beautiful, clean boat. Guests also mention how memorable it is—whether celebrating a birthday, enjoying a romantic outing, or just escaping the city for a peaceful hour or two.

While food and drinks are not included, you’re encouraged to bring your own. Many guests bring snacks and beverages, creating a relaxed, picnic-like atmosphere on the water. The experience is great for those who love being outdoors and want an authentic, local perspective of Chicago.

Who Will Love This Tour?

If you’re seeking a private, scenic, and relaxed way to see Chicago’s skyline, this sail is ideal. It’s perfect for celebrating special occasions, romantic getaways, or just enjoying a peaceful break from busy city life. The customizable itinerary and knowledgeable guides make it appealing for history buffs and architecture enthusiasts alike.

Travelers who appreciate personalized experiences and want to avoid crowded boat tours will find this private sailing to be a refreshing change. It’s also well-suited for groups of friends or family who want intimate, memorable time together with stunning views as a backdrop.

If weather is a concern, just remember that the tour can be canceled for poor conditions, but the company offers full refunds or rescheduling options, providing peace of mind.

FAQs

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

Where does the tour start?
It begins at 801 E Grand Ave, Chicago, right at Navy Pier Marina, which is a convenient and well-known location.

Is this experience suitable for children or non-sailors?
Most travelers can participate, and the experience is generally suitable for most ages. However, children should be comfortable on a boat, and safety guidelines must be followed.

Can I bring my own drinks?
Yes, you can bring and consume reasonable amounts of alcohol, following Illinois law. Just avoid glass containers—plastic cups are recommended.

What if the weather is bad?
The tour requires good weather. If canceled due to poor conditions, you’ll be offered a different date or a full refund.

Is there parking available?
Parking is not included, and Navy Pier parking can be expensive, so plan accordingly.

Can I take photos during the tour?
Absolutely—there are plenty of great photo opportunities, especially with the city skyline and landmarks as your backdrop.

Final Thoughts

This private sailing tour on Lake Michigan offers an excellent way to see Chicago from a new perspective. Its personalized nature, combined with stunning views of the skyline, makes it a memorable experience for couples, families, or friends celebrating a special occasion. The knowledgeable captains, comfortable boat, and flexible itinerary ensure you’re not just along for a ride but part of a tailored adventure.

While it does require good weather and involves a higher price point, many reviewers agree that the intimacy and exclusivity add tremendous value. If you love being on the water, enjoy spectacular city views, and want to steer your own little piece of Chicago, this sail is well worth considering.

In brief, this experience is perfect for those who desire a quieter, more personal way to take in the city’s beauty and enjoy quality time on Lake Michigan. It’s an authentic, memorable, and scenic escape that’s likely to be one of your trip’s highlights—no matter if you’re celebrating a milestone or just seeking a peaceful day away from the hustle.