Private Sailing on Beautiful Lake Michigan – Navy Pier, Chicago

A Closer Look at Private Sailing on Lake Michigan from Navy Pier, Chicago

If you’re seeking a way to see Chicago from a fresh vantage point, a private sailing trip on Lake Michigan might just be your perfect answer. This experience offers an intimate, relaxed way to enjoy the city’s iconic skyline, with the flexibility to tailor your outing to what interests you most. While we haven’t personally been on this specific tour, reviews and details paint a picture of a memorable and valuable adventure.

What immediately stands out is the personalized nature of the trip and the expert guidance offered by friendly, knowledgeable captains. The chance to take the helm or just kick back with your favorite tunes on Bluetooth speakers makes it clear this experience is about quality, comfort, and fun. That said, it’s good to keep in mind that it’s a two-hour trip, so it’s best suited for those with a flexible schedule and a love for water-based activities. This sail is ideal for couples, families, groups celebrating special occasions, or anyone wanting a unique Chicago story to tell.

Key Points

• Fully customizable itineraries allow you to focus on what interests you most.
• The two-hour duration offers enough time for a relaxed yet engaging experience.
• Expert US Coast Guard licensed captain guides the boat, ensuring safety and knowledge.
• The exclusive private group makes for a personalized, intimate outing.
• You can bring your own music via Bluetooth, adding a personal touch.
• The experience is well-reviewed—a perfect blend of scenic beauty and informative guidance.

Why Choose a Private Sailing Tour in Chicago?

Chicago’s skyline is world-famous, and while many visitors admire it from street level or from tall observation decks, seeing it from the water offers a whole new perspective. The views of the city’s architecture, the Adler Planetarium, Soldier Field, and even the historic Queen Elizabeth II visit, all become more vivid when viewed from Lake Michigan.

This tour’s value extends beyond just sightseeing. It provides an unmatched sense of tranquility in a busy city, where you can relax aboard a well-maintained sailboat, listen to your favorite tunes, and soak in the scenery. Many reviews highlight how the experience feels exclusive—your own private slice of Chicago’s water.

What to Expect During the Itinerary

Departure from Navy Pier Marina

Your adventure begins just off Navy Pier’s north side, a central and accessible starting point. After a brief safety briefing, you’ll be ready to set sail. The departure location itself is worth noting because Navy Pier is a major Chicago icon, and watching the city from this spot adds to the anticipation.

Cruising Past Chicago Landmarks

As the boat glides out onto Lake Michigan, you’ll immediately notice the spectacular city skyline. Many reviews mention how “time flew by,” with captains sharing stories about the city’s architecture and history. Highlights include Grand Ballroom, the Adler Planetarium, and the historic Soldier Field—all visible from the water, giving you a fresh appreciation of Chicago’s design and development.

Customizable Route Options

Because the itinerary is fully flexible, your captain will tailor the route to your interests. Whether you want to focus on capturing that perfect skyline shot, learn about Chicago’s history, or just enjoy the tranquility of the lake, the captain adapts accordingly. This makes each trip feel personal—a significant advantage over more generic group tours.

Enjoying the Water and Views

The tour’s two hours offer ample time to relax, take photos, or even try your hand at steering the boat if you’re feeling adventurous. One notable feature is the Bluetooth speaker setup, allowing you to play your own playlist—a small touch that elevates the experience.

Return to Navy Pier

After approximately two hours, the sail concludes back at the marina. Many reviews mention how difficult it is to leave, with some wishing for longer trips, but the short duration is perfect for a quick escape or a break during a busy city visit.

The Experience and the Guides

What do travelers rave about? According to reviews, Captain Mike and Captain Ulysses are both praised for their friendly professionalism and wealth of knowledge. Guests appreciate how they’re willing to answer questions about sailing, Chicago landmarks, and the lake’s history.

Many mention the clean boat, the comfortable setting, and the informative commentary. Several reviews highlight the personalized attention—with captains making efforts to ensure everyone feels engaged, whether through storytelling or inviting guests to participate in sailing.

Pricing and Value

At $566.82 for a group of up to six people, this private tour might seem steep at first glance. However, when you consider the exclusive access, personalized route, expert guidance, and the overall experience, it becomes clear this is about value rather than just cost. For a special occasion—birthday, anniversary, or just a memorable day in Chicago—this private sail offers a level of intimacy and flexibility that larger tours can’t match.

Plus, the price covers all taxes, the Navy Pier facility fee, and the use of Bluetooth speakers—no surprising extra charges. Food and drinks are not included, but you’re welcome to bring reasonable alcohol in secure containers, making it easy to customize your onboard experience.

Practical Tips for Planning Your Trip

• Start times are flexible—choose a time that best fits your schedule, especially if you want to catch sunset views.
• Parking at Navy Pier can be pricey, so plan accordingly. Public transportation is a good alternative.
• Since it’s a private tour, you control the experience to some extent—so communicate any special requests or interests to your captain beforehand.
• Dress comfortably and bring layers, as it can get breezy on the water.
• Bring your own music for a personalized soundtrack—just connect via Bluetooth.

Who Is This Tour Best For?

If you love a mix of scenic beauty, a touch of adventure, and personalized service, this cruise hits the mark. It’s perfect for romantic couples, families wanting a unique outing, or groups celebrating a special event. Those seeking a peaceful yet engaging way to see Chicago from a different angle will find this sail rewarding.

Final Thoughts

This private sailing experience on Lake Michigan offers more than just a boat ride—it’s a chance to see Chicago through a different lens, with added comfort, flexibility, and personal attention. The weather can make or break outdoor water adventures, so keep an eye on the forecast, but with good conditions, you’re likely to find this trip a highlight of your visit.

Travelers who value expert guides, stunning vistas, and the freedom to customize their experience will find this tour well worth the price. It’s an authentic, memorable way to connect with Chicago’s iconic water and skyline—an experience that’s sure to leave lasting impressions.

FAQ

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

Where does the trip depart from?
It departs from Navy Pier Marina, on the north side of Navy Pier, a very central and accessible location in Chicago.

How many people can participate?
Up to 6 guests can join this private tour, making it ideal for small groups or families seeking exclusivity.

What’s included in the price?
The cost covers the professional US Coast Guard licensed captain, use of Bluetooth speakers, all taxes, and the Navy Pier facility fee.

Can I bring my own drinks?
Yes, you can bring reasonable amounts of alcohol in secure containers, but glass bottles are prohibited.

Is the tour suitable for children?
While most travelers can participate, consider the age and comfort level of children, especially since it’s a water-based activity.

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

Can I participate in sailing or steer the boat?
Yes, if you wish, you can take a turn at the helm, adding a fun, interactive element to your trip.

Are food and drinks provided?
No, but you’re welcome to bring your own. Food and beverages are not included in the package.

Is there parking nearby?
Parking at Navy Pier can be expensive, so public transit or nearby parking garages are recommended.

In the end, this private sailing tour offers a blend of scenic beauty, expert guidance, and personalized service—a perfect way to see Chicago from a fresh angle. Whether celebrating a special day or simply craving a peaceful escape, it’s a memorable, authentic experience worth considering.