Private Sailing on Beautiful Lake Michigan – Navy Pier, Chicago

Imagine gliding across Lake Michigan, with the skyscrapers of Chicago shimmering in the background and the city’s lively waterfront unfolding around you. That’s exactly what you get with the private sailing experience from Navy Pier, offered by Come Sailing This isn’t your typical sightseeing cruise—it’s a chance to see Chicago from a fresh perspective, on a boat all to yourself or with a small group of friends or family.

From the moment you step aboard, you’ll notice how this tour combines tailored experiences, knowledgeable hosts, and incredible views that make for a memorable day on the water.

What we particularly love about this tour is how customizable it is—your itinerary is flexible, allowing you to focus on what excites you most. Plus, the opportunity to take the helm if you’re feeling adventurous adds an interactive touch that many tours don’t offer. The other highlight is just how beautiful and varied the scenery is, from Chicago’s iconic skyline to historic landmarks and tranquil open water.

On the flip side, keep in mind that this is a 2-hour experience with no included food or drinks, so it’s best suited for those who are comfortable with a short sailing outing and prepared with their own snacks if needed.

This tour suits travelers who want a relaxed, personal, and scenic escape from the usual city sights. It’s perfect for special occasions, romantic outings, or just a unique way to enjoy Lake Michigan away from crowded boat tours. Expect to learn a bit about sailing and Chicago’s architecture, all while basking in the sun and soaking up breathtaking views.

This experience made our article of Our 3 Favorite Chicago Sailing Experiences.

Key Points

• Fully customizable itineraries allow you to focus on what interests you most, whether it’s skyline views or sailing basics.
• Intimate experience with up to six guests, making it ideal for small groups or couples seeking privacy.
• Knowledgeable captain who offers insight into sailing, Chicago landmarks, and local history, making your trip educational as well as scenic.
• Flexible start times help you fit the experience into your schedule, whether morning or afternoon.
• Includes Bluetooth speakers so you can play your favorite tunes while sailing—making the experience more personal.
• Stunning views of Chicago’s skyline, Navy Pier, and iconic landmarks like Soldier Field and the Adler Planetarium from the water.

Starting Point and Overall Layout

The adventure begins at Navy Pier Marina, one of Chicago’s most recognizable landmarks and tourist magnets. Departing from this bustling hub gives you an immediate sense of being in the heart of Lake Michigan’s scenic waterfront. The boat itself is a well-maintained, comfortable vessel, suitable for a small group seeking an exclusive experience.

Once aboard, your captain will conduct a safety briefing and prepare the boat. From there, the two-hour sail unfolds, offering a perfect balance of relaxation and activity. As you glide out of Navy Pier, the sights start to unfold—Chicago’s tall buildings, historic sites, and natural beauty all come into view.

The Route and Key Stops

The tour’s itinerary is designed to showcase Chicago’s most iconic waterfront sights, but with the flexibility to customize.

• Navy Pier: Your departure point is a landmark itself, providing great photo opportunities and a sense of excitement as you set out.
• Chicago Skyline: The towering skyscrapers of the Loop and beyond are best appreciated from the water, and your captain will likely point out notable buildings and architectural highlights. Several reviews praise the “stunning views of the city’s architecture,” which truly are best experienced from this vantage point.
• Historic Landmarks: The Adler Planetarium, sitting on Northerly Island, is a highlight. Built in 1930, it’s a picturesque domed structure, visible from the water and often remarked upon by guides for its charm.
• Soldier Field: The home of the Chicago Bears is another recognizable sight, with history and modern renovations adding to its character.
• Royal Visit Landmark: Passing Monroe Harbor, you’ll see the site connected to a notable royal visit in 1959 when Queen Elizabeth II was ferried across the lake—an interesting tidbit your captain might share.

What to Expect During the Sail

The experience is crafted to be relaxed, with room for interaction, learning, and fun. You’ll spend most of the time on deck, with the option to take a turn at the wheel if you’re feeling confident. The boat is equipped with Bluetooth speakers, so feel free to bring along your playlist. The captain is known for being friendly and knowledgeable—many reviews mention Captain Mike or Ulysses, who are praised for their professionalism and storytelling.

The two-hour window allows for a gentle sail, some picture-taking, and enjoying the scenery without feeling rushed. Because the tour is private, your group’s interests shape the experience—such as focusing on photography, sailing, or simply relaxing.

Comfort and Practicalities

The boat is described as clean and comfortable, with enough room for everyone to spread out. Food and drinks are not included, but you can bring your own—just remember that glass containers are prohibited, and all spills should be cleaned up to avoid extra charges.

The tour includes all taxes and the Navy Pier facility fee, so there are no hidden costs. Parking is not included, so plan ahead if you’re driving; public transportation options are nearby.

The Cost and Value

Priced at $566.82 per group (up to six people), many reviewers agree this represents good value for an exclusive, private outing. For that price, you get a tailored experience, a professional captain, and the chance to see Chicago from a perspective few travelers explore—on the water amidst the city’s iconic skyline.

Considering the rave reviews about the guides’ friendliness and knowledge, as well as the stunning views, this tour offers a memorable experience. For special occasions or those wanting a quieter, more personal alternative to larger, crowded boat tours, it’s an excellent investment.

The Review Summary from Travelers

Reviewers consistently rate this experience a perfect 5 out of 5, with many mentioning how it topped their trip. Comments highlight the “fantastic” time, especially for celebrating birthdays or anniversaries, and rave about the friendly, capable guides who shared interesting Chicago facts. Several mention how the views from the water surpassed any land-based sightseeing, emphasizing the “incredible downtown” and lakefront vistas.

Many expressed a desire to do it again, and one even noted that it was the “highlight of their girls’ weekend.” The intimate setting, combined with knowledgeable hosts, makes all feel welcomed and well looked after.

This private sailing tour is best for travelers seeking a personalized, relaxed way to experience Chicago’s waterfront. It suits those celebrating special occasions, couples craving a romantic outing, or groups of friends who want a unique shared experience. It’s also ideal for visitors interested in learning about sailing, architecture, or Chicago’s history, all from the comfort of a well-maintained boat with a friendly captain guiding the way.

If you’re after a lively party atmosphere or a large group experience, this might not be the fit. But if you value intimacy, customization, and stunning scenery, this tour is a winner.

Absolutely, especially if your goal is to see Chicago from a fresh, scenic angle without the crowds. The private nature of the tour, combined with the ability to customize your route and the knowledge of your captain, makes this a special way to spend a few hours. The views of Chicago’s skyline, the historic landmarks, and the calm water all create a peaceful yet exciting environment—perfect for making memorable moments.

While it’s a relatively short trip—just two hours—the experience feels rich and personal. The lack of included food or drinks isn’t a dealbreaker; you can bring your own snacks and beverages, making it easy to tailor the experience to your preferences. And with a flexible schedule and the chance to take part at the helm, this sailing adventure offers genuine engagement for those interested in a hands-on, intimate outing.

In short, this is an authentic, value-packed way to enjoy Lake Michigan’s beauty and Chicago’s impressive architecture, all while sailing on a private boat with expert guidance.

Can I customize the itinerary?
Yes, the tours are fully customizable to suit your group’s interests, whether you want more sightseeing, sailing, or relaxing.

How many people can join?
Up to six guests per booking, making it ideal for small groups, couples, or families seeking privacy.

What’s included in the price?
The price covers the captain, Bluetooth speakers for music, all taxes, and the Navy Pier facility fee.

Are food and drinks provided?
No, food and drinks are not included, but you’re welcome to bring your own, with the restrictions on glass containers.

Is parking available?
Parking is not included; plan ahead or use nearby public transportation options.

What if the weather is bad?
The captain reserves the right to cancel for weather reasons, with rescheduling or full refund options.

Can I swim during the tour?
Swimming might be permitted on tours longer than three hours, but it’s at the captain’s discretion and requires signing a waiver.

Are smoking and alcohol allowed?
Smoking is strictly prohibited, but reasonable amounts of alcohol are permitted, with no glass containers.

Can I bring my pet?
Animals are not allowed on board, so plan for your pet’s care elsewhere.

Whether you’re celebrating a special moment or simply looking for a peaceful way to see Chicago from the lake, this private sailing tour offers a uniquely personal experience. It combines scenic beauty, expert guidance, and complete control over your itinerary—a perfect way to make your Chicago visit even more memorable.