Come Sailing with us at Navy Pier: Sunset Sail on Lake Michigan

Imagine gliding across Lake Michigan just as the sun dips below the Chicago skyline. That’s exactly what this private sunset sailing tour offers — a chance to see one of America’s most iconic cities from a fresh, water-based perspective. Whether you’re celebrating a special occasion or just seeking a quiet moment with loved ones, this experience promises a relaxed yet unforgettable view of Chicago’s stunning waterfront.

What we love about this tour is the personalized approach — you get to choose your route, music, and even up to five additional guests. Plus, it’s led by a US Coast Guard–certified captain, which adds a reassuring layer of safety and expertise. On the flip side, one thing to keep in mind is that this experience costs around $508 per group, which might seem steep for some, but the intimate, private nature of the cruise offers good value for a tailored experience.

This cruise feels best suited for groups looking for a memorable, flexible, and scenic outing. No doubt, it’s a hit with couples, families, or friends celebrating a milestone. If you’re after a more crowded boat with touristy commentary, this might not be your best fit — but for those craving an authentic, personalized adventure, it hits the mark.

Key Points

• Private, customizable sailing experience with up to 6 guests
• Spectacular views of Lake Michigan and Chicago’s skyline
• Led by a US Coast Guard–licensed captain for safety and local knowledge
• Flexibility to choose route, music, and landmarks
• Includes refrigerator and ice for drinks and snacks
• Ideal for special celebrations or intimate outings

The Itinerary: What You Can Expect

The tour departs from Navy Pier Marina, a lively Chicago landmark that’s worth exploring even before your sail (think: shops, restaurants, and photo ops). The initial safety briefing prepares you for a smooth trip, after which your captain takes the helm. Since this is a private charter, the route isn’t fixed — expect a lot of flexibility based on wind conditions and your preferences.

Navy Pier itself offers a striking backdrop as you head out, with the Grand Ballroom and other historic structures passing by in the blink of an eye. Many reviews mention how great it is to sail past this spot, with Elizabeth noting, “Wonderful city views, pleasant conversation about sailing, and a memorable experience for us all.”

As you move along, the skyline unfolds in all its glory — tall glass skyscrapers, historic buildings, and landmarks like Soldier Field, which retains some of its original colonnades despite its modern renovations. The captain can point out the various architectural feats, but you’re also free to just soak in the view and enjoy the moment.

One less obvious highlight is the view of the Adler Planetarium’s distinctive dome — a classic Chicago sight that appears even more impressive from the water, especially at sunset. The tour passes close enough to appreciate its lakeside setting, which most land-based visitors don’t see.

Another “must-see” along the route is the Buckingham Fountain, a Chicago icon and one of the world’s largest fountains. The captain might slow down here, giving you a perfect chance for photos. With the sunset casting a warm glow, waves of orange and pink reflect off the water, making for a magical moment as Elizabeth describes, “The sunset was gorgeous and perfect.”

Finally, the cruise ends back at Navy Pier, with ample opportunities for photos and reflection on what may be the best view of Chicago you’ve ever experienced.

What Makes This Experience Special

Many reviews emphasize how the personalized nature of the tour elevates it beyond a typical boat ride. Captain Mike, for example, is praised for his knowledge, friendliness, and flexibility. Daniel shares, “Captain Mike was easy to talk to and made us feel safe but also let us eat and play music. I couldn’t ask for anything better.” This highlights how the captain not only ensures safety but also adapts to your wishes, whether you want a leisurely sail, music, or a quiet moment.

The view of the Chicago skyline at sunset is a recurring highlight. As Christine notes, “The sunset cruise was gorgeous and perfect. We got day views, sunset views, and night views — so special.” The gentle ride on a private boat, combined with the changing light, makes for a truly memorable experience.

Authentic reviews also mention how relaxed and comfortable the experience feels. Many guests highlight the smooth sailing, the ability to bring their own drinks and snacks, and how the captain’s local insights added depth to the trip.

Analyzing the Cost and Value

At just over $500 for a group of up to six, this sail isn’t cheap, but it’s important to consider what you’re getting. The price includes the private boat, a licensed captain, all taxes, and the Navy Pier facility fee. For a personalized, intimate experience with spectacular views and the freedom to customize your route, many find it well worth the expense.

Compared to crowded boat tours or expensive dinner cruises, you’re paying mainly for the privacy, flexibility, and the chance to set your own pace. If you’re celebrating a significant event like a birthday or anniversary, the cost becomes more justifiable given the memorable ambiance.

Practical Details

The tour lasts approximately two hours, starting at 801 E Grand Ave near Navy Pier. You’ll want to arrive a little early for the safety briefing and to get comfortable. The experience is suitable for most travelers, with most conditions geared towards safe, smooth sailing.

Since the tour is completely private, you won’t be sharing the boat with strangers — a major plus for those wanting privacy and a relaxed atmosphere. The group size is limited to six, ensuring an intimate setting.

You can bring your own food and drinks — just avoid glass containers for safety and environmental reasons. The boat has a refrigerator and ice, making it easy to keep beverages chilled. Remember, smoking, swimming, and bringing animals are prohibited for safety and comfort.

Weather plays a crucial role; the captain can cancel if conditions are unsafe, but if that happens, you’ll be offered a reschedule or a full refund. Keep an eye on the forecast if you’re planning a sunset sail, as wind or storms could impact your plans.

FAQs

How far in advance should I book? The average booking window is about 43 days ahead, so it’s wise to reserve early, especially during peak seasons or weekends.

What is included in the price? The cost covers the private boat, a US Coast Guard–licensed captain, all taxes, and the Navy Pier facility fee. You need to bring your own drinks and snacks.

Can I bring alcohol? Yes, guests may bring their own alcohol and enjoy it responsibly onboard, but glass containers are prohibited for safety.

What if the weather is bad? The captain can cancel the trip if conditions are unsafe. In such cases, you’ll be rescheduled or offered a full refund.

Is the tour suitable for children? The tour is generally suitable for most travelers; however, swimming is prohibited, and children should be supervised. The private nature makes it a good option for family groups.

What’s the best time of day for this tour? The sunset timing is ideal; the tour lasts about two hours, and the experience is most magical during the hour before dusk.

Is parking available? Parking isn’t included; you’ll need to find your own near Navy Pier. Consider public transit options for convenience.

Final Thoughts

This private sunset sail at Navy Pier offers a unique and personalized way to see Chicago from the water. It’s a calm, scenic, and flexible experience that emphasizes comfort, safety, and stunning views. If you’re looking to celebrate a special occasion, or simply want a peaceful escape from the city’s hustle, this tour delivers.

The ability to customize your route and music, combined with the expert guidance of a US Coast Guard–certified captain, makes it a standout option for those seeking a tailored and authentic Chicago experience. The reviews speak volumes about how memorable and enjoyable this cruise is, with many calling it the best way to view the city’s skyline.

While it’s somewhat pricier than a standard boat ride, the private setting and flexibility justify the cost for most travelers looking for a special outing. It’s especially well-suited for small groups, couples, or families who value intimacy and personalized service.

If you want a peaceful, scenic, and deeply personal way to take in Chicago’s beauty, this sunset sail is a highly recommended choice. Just remember to book early, check the weather, and come prepared to relax and enjoy one of the city’s most beautiful perspectives.

Happy sailing!