Private Sailing on Beautiful Lake Michigan – Navy Pier, Chicago

Looking for a relaxing, scenic way to see Chicago from a different perspective? This private sailing tour on Lake Michigan might just be what you need. While I haven’t personally taken this exact trip, the glowing reviews and detailed descriptions paint a clear picture: it’s an intimate, customizable experience that offers a unique view of the Windy City’s skyline and waterfront.

One of the things I really appreciate about this tour is the flexibility it offers. With fully customizable itineraries and the ability to set your own start time, it’s tailored to your preferences—whether you want a quick afternoon sail or a more leisurely exploration. Plus, the inclusion of a knowledgeable US Coast Guard-licensed captain means you’re in good hands, ready to learn, relax, or even take the helm if you feel like it.

However, one consideration worth noting is the price point—around $566.82 for a group of up to six. While this might seem steep at first glance, the value lies in exclusivity, personalized service, and the gorgeous views that come with it. This experience tends to attract those looking for a special occasion or a memorable day out on the water, rather than a casual group activity. If you’re after a private, scenic escape with a touch of luxury, this could be a perfect fit.

This sailing trip suits travelers who appreciate a mix of relaxation, stunning visuals, and a bit of personal interaction with the crew. Whether celebrating a birthday, anniversary, or just seeking a peaceful way to enjoy Chicago’s iconic skyline, this tour has something to offer.

Key Points

• Exclusive experience: Only your group will be on the boat, offering privacy and personalized attention.
• Customizable itinerary and schedule: You can choose start times and tailor the route to your interests.
• Stunning views: Expect impressive sights of Navy Pier, Chicago’s skyline, and landmarks like the Adler Planetarium and Soldier Field.
• Informative and friendly crew: Passengers praise the captains for their knowledge and friendliness.
• Music on board: Bluetooth-enabled speakers allow you to set your playlist and create a fun, relaxed vibe.
• Good value for special occasions: While not cheap, the experience provides a memorable, intimate outing that’s often highlighted as a highlight of trips to Chicago.

An In-Depth Look at the Experience

Starting Point and What to Expect at Navy Pier

The tour kicks off at Navy Pier Marina, a bustling Chicago landmark and one of the city’s most visited spots. You’ll meet your captain and crew here, and after a quick safety briefing, the sails are set. The dock lines will be taken aboard, and from that point, the adventure begins. Navy Pier itself is a lively backdrop, and sailing past it offers a wonderful contrast between the busy shore and the calm lake waters.

The Itinerary and Stops

The tour is designed to be flexible, with the captain steering a route that highlights the best views and interests of your group. You can expect to see several iconic sights:

• Chicago skyline: The views from the water are often described as breathtaking. The towering skyscrapers, the gleam of the buildings, and the overall majesty of the city look especially stunning from Lake Michigan. One reviewer mentioned how the views of the skyline are “best seen from the water,” and we agree—seeing the city from this angle is a different, more immersive experience.

• Adler Planetarium: Sitting on Northerly Island, this distinctive dome is a recognizable Chicago landmark and a photo-worthy stop. The combination of the planetarium’s architecture and the lake backdrop makes for a memorable shot.

• Soldier Field: Known as the home of the Chicago Bears, this stadium’s history and size are impressive even from afar. It’s one of the many interesting sights along the water.

• Royal Visit: An amusing highlight mentioned in reviews is the passage of a barge ferrying Queen Elizabeth II in 1959. It’s a little piece of history that adds flavor to your cruise.

The Experience on the Water

The 2-hour trip is just enough time to relax, take in the scenery, and enjoy some gentle sailing. Reviewers often comment on the boat’s cleanliness and comfort, which makes a significant difference in how much you enjoy the trip. The onboard Bluetooth speakers mean you can set your own soundtrack—whether that’s a playlist of your favorite tunes or some relaxing background music.

Many guests have expressed how they could have stayed out longer—it’s that peaceful and enjoyable. The captain’s knowledge adds another layer, as they’re happy to answer questions about sailing, Chicago history, or the sights passing by. Several reviews mention captains like Mike or Ulysses, praising their friendliness, competence, and storytelling skills.

Food, Drinks, and Other Amenities

While food and drinks are not included in the price, guests are allowed to bring their own, including reasonable alcoholic beverages, which can enhance the experience. Just remember, glass containers aren’t permitted, so keep your wine or champagne in plastic cups or bottles in protective sleeves. Passengers often bring snacks, drinks, or even music to personalize their trip.

The boat’s environment is designed for comfort, with plenty of space to spread out. Some reviews mention enjoying a relaxed atmosphere with friends or family, making for a memorable celebration or just a peaceful escape from the city buzz.

Practical Details and Considerations

• Price: At around $566.82 for up to six people, you’re paying for privacy, exclusivity, and a tailored experience. For special occasions or a romantic escape, many find it worth the splurge.

• Duration: Two hours might seem short, but it’s enough to see many sights and enjoy the tranquility of the lake. Longer trips are available in other experiences, but this length keeps it manageable and fun.

• Booking Flexibility: The ability to choose from several start times makes it easy to fit into your schedule, whether you want a morning calm or a sunset sail.

• Weather and cancellations: The captain can cancel due to weather or mechanical issues but will reschedule or provide a full refund if needed. Keep an eye on the forecast for the best experience.

• Behavior and safety: The crew emphasizes respectful conduct, and smoking or weapons are strictly prohibited. Seasickness can occur; if you’re prone, it’s best to be prepared and stay on deck if you feel unwell.

What Reviewers Love Most

Many guests highlight the expertise and friendliness of the captain—names like Mike and Ulysses come up often. They’re praised for their knowledge, patience, and the way they enhance the trip with stories and insights. The views are consistently described as “spectacular,” especially when passing Chicago’s famous landmarks.

The atmosphere is often described as intimate and relaxing, with music, drinks, and good company making the trip even better. Several reviews detail how this trip was the highlight of their visit, with some mentioning it as the best part of their vacation.

Who Should Consider This Tour?

This private sailing experience is best suited for those seeking a personal, relaxing outing on Lake Michigan. It’s ideal for celebrating special moments, like birthdays or anniversaries, thanks to the customizable itinerary and exclusive nature. It also appeals to travelers who want to see Chicago from a different angle and enjoy a peaceful, scenic ride away from crowded tours.

If you’re comfortable with a bit of wind and open water, and looking for a memorable, intimate experience, this tour hits the mark. Keep in mind, it’s not a party boat, nor does it include food or drink—so if you’re after a full meal or lively party, you might want to look elsewhere.

FAQ

Is this tour suitable for children or families?
While the experience is more adult-focused, it’s open to most travelers who are comfortable on open water. Children who can handle being on a boat and are respectful of safety guidelines should be okay, but there’s no specific mention of family-friendly features.

Can I bring my own food and drinks?
Yes, you’re welcome to bring food and beverages, including alcohol, within Illinois law. Just remember to avoid glass containers and use plastic cups for drinks.

How long is the tour?
The standard tour runs about 2 hours, which gives plenty of time to see key sights and enjoy a relaxing sail without feeling rushed.

What is included in the price?
The fee covers the boat, a licensed captain, use of Bluetooth speakers, all taxes, and the Navy Pier Facility Fee.

What if the weather is bad?
The captain reserves the right to cancel due to weather or mechanical issues. If canceled, you’ll be offered a reschedule or a full refund.

Can I take the helm?
While the guide is onboard to steer, you are welcome to ask if you’d like to take a turn at the wheel—depending on the captain’s discretion and your comfort level.

Final Thoughts

All in all, this private sailing tour on Lake Michigan offers a special way to experience Chicago. It’s perfect for couples, small groups, or anyone wanting a peaceful, intimate escape with stunning skyline views. The combination of personalized service, flexible scheduling, and a gorgeous setting makes it stand out from typical Chicago tours.

While the price isn’t pocket change, the exclusivity and quality of the experience often make it worth it. If you’re celebrating a special occasion or just want a quiet, scenic way to enjoy the city’s waterfront, this trip promises a memorable, relaxing outing.

This experience isn’t for those seeking a lively, party atmosphere or a large group adventure. Instead, it’s best for travelers who value comfort, intimacy, and a personal touch while soaking in some of the best scenery Chicago has to offer.

Happy sailing, and I hope you find the perfect day to see Chicago from Lake Michigan!