Navy Pier Chicago: Private Sailboat Charter with Captain

Set sail on a private Chicago adventure with a 2.5-3 hour cruise along the glittering Lake Michigan. Departing from the brand-new Navy Pier Marina, this experience offers an intimate voyage aboard a well-maintained sailing yacht. With room for up to 7 guests, it’s perfect for friends, family, or a small celebration. You’ll enjoy the wind in your hair, panoramic views of Downtown Chicago, and options to swim, relax, or even take the helm. The experience is all about sophisticated comfort combined with a laid-back, fun vibe, making it a standout way to see the city from a different perspective.

What we love most is how personalized this cruise is — from the chance to bring your own drinks to the on-board surround sound speakers playing your playlist. Plus, the amenities like a swim platform, fridge, and bathroom elevate it from a simple boat ride to a genuine mini-getaway. That said, if you’re looking for a larger group or a more structured tour, you’ll need to inquire about additional arrangements.

This experience is ideal for travelers who appreciate comfort, exclusivity, and a touch of adventure—perfect for a romantic outing, a celebration, or just a fun day with friends. Keep in mind, it’s not suited for those with mobility challenges or seasickness, but if you’re eager for a relaxed, scenic sail, you’ll find it hard to beat.

Key Points

• Private Experience: Up to 7 guests enjoy exclusive access aboard a well-kept sailing yacht.
• Scenic Views: Sail past Downtown Chicago, Navy Pier, and the Chicago Lighthouse with spectacular skyline views.
• Flexible Activities: Swim in Lake Michigan, relax on deck, or take the helm — your choice.
• All-Inclusive Comfort: Drinks, snacks, a bathroom, and a kitchen are included; BYO is welcome.
• Safety & Licensing: Fully licensed, insured, and maintained to US Coast Guard standards.
• Additional Requests: Catering, provisioning, or larger groups are available upon inquiry.

You can check availability for your dates here:

Exploring the Chicago Private Sailboat Experience

Starting Point and Meeting Details

Your adventure begins at the Navy Pier Marina, conveniently located in downtown Chicago. The exact meeting instructions are sent after booking, but the coordinates (41.892154, -87.607483) place you right at the heart of the action. This prime location makes it easy to combine your sailing with other downtown attractions or a day exploring Navy Pier itself.

The Yacht and Amenities

You’ll be aboard a meticulously maintained sailing yacht equipped with large open cockpit seating and modern comforts. The boat includes a fully stocked kitchen, a bathroom and changing room, and a swim platform with amenities like a rinse shower, lily pad, noodles, life jackets, and floaties. Whether you want to relax, swim, or jump into Lake Michigan, there’s plenty of gear to enhance your experience.

What to Expect During the Cruise

Your sailing adventure lasts around 2.5 to 3 hours—a perfect window to relax without feeling rushed. The experience is all-inclusive, with complimentary beverages and snacks, or you can opt to bring your own drinks—alcohol is allowed. Onboard, Bluetooth speakers let you play your favorite tunes, adding a personal touch to your cruise.

You might be surprised by the variety of options available—from simply soaking in the skyline views, especially at sunset, to actively participating by taking the wheel or swimming in Lake Michigan. Some reviews mention how “feeling the wind in your hair” and “jumping into the lake at anchor” are favorite parts. Others appreciate the professionalism and hospitality of the crew, making sure every detail is handled smoothly.

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Highlights of the Experience

• Scenic Cruising: Glide past iconic sights like Navy Pier and the Chicago Lighthouse, with plenty of photo opportunities.
• Swim & Float: The anchoring in the Chicago Playpen offers a chance for a refreshing swim or float party, with safety gear and rinsing facilities.
• Relax & Play: Lounge on deck or get active, with the option to take control of the sail or jump in the water.
• Music & Snacks: Enjoy your playlist via Bluetooth surround sound while nibbling on snacks stored in the fridge.

The Value Proposition

Considering the price includes fuel, drinks, snacks, water toys, and safety gear, it offers a solid value for a private, VIP experience. Compared to larger, more generic boat tours, this one emphasizes personalized service and authenticity—you’re not just another passenger but a small group enjoying a tailored outing.

Potential Drawbacks

One thing to keep in mind is group size limitation—up to 7 guests—and the need for guests to be comfortable with water activities or moving around on a boat. If you have mobility issues or seasickness, this might not be ideal. Also, if you’re planning for a larger group, inquire about arrangements for up to 12 people, as the standard package accommodates smaller parties.

Who Should Book This?

This cruise appeals most to couples, small groups, or families seeking a unique Chicago experience. It’s perfect if you want to combine sightseeing with a relaxed, fun day on the water, away from crowded boat tours. It’s also ideal for celebrating special occasions—anniversaries, birthdays, or just a sunny day with friends.

A Closer Look at the Itinerary and Experience

Embarking from Navy Pier

Starting at Navy Pier, you’re already immersed in the lively heart of Chicago. You’ll meet your captain and crew, who are licensed, permitted, and insured to meet US Coast Guard safety standards. Once aboard, the boat is yours, and the crew takes care of everything, from safety to navigation.

The Sailing Itself

The first part of your trip involves setting sail along the Chicago Lakefront. We loved the way the yacht glides smoothly over the water as the skyline approaches. The captain or crew member may lead you on the helm, giving you a chance to steer if you wish—an authentic and engaging experience that’s not often available on larger, commercial tours.

Stops and Activities

The main highlight is the anchoring in the Chicago Playpen, a designated spot near the city where you can swim or relax. The swim platform is especially appreciated, with a rinse shower to cool off after swimming or floating. The opportunity to jump into Lake Michigan and float around on noodles or lily pads is a hit among guests.

Relaxation and Entertainment

Whether you’re sunbathing on deck, listening to music, or enjoying snacks, the yacht’s open layout creates a casual and intimate setting. The Bluetooth surround sound system means you can dictate the soundtrack—be it relaxing tunes or your favorite playlist—enhancing the mood.

The Return and Ending

As the cruise winds down, you’ll head back toward Navy Pier, with ample time to snap photos of the Chicago skyline at sunset or in the early evening. Many reviews note how the experience feels both exclusive and accessible, with a relaxed atmosphere that makes everyone feel comfortable.

Authentic Experiences from Guests

Guests praise the “attention to detail” and “hospitality” of the crew, with many emphasizing the personalized service. One reviewer said, “It’s a very relaxing experience, perfect for celebrating or just unwinding.” Others appreciated the flexibility—bringing their own drinks or music—and how the boat was equipped with everything needed for a fun, safe outing.

Some mention the beautiful skyline views as the highlight, especially at sunset, when the city lights begin to sparkle. The ability to swim and float in Lake Michigan adds an adventurous splash to the trip, making it more than just a sightseeing cruise.

Who Is This Experience Best For?

If you’re someone who values privacy and comfort, this cruise hits the mark. It’s especially good for small groups or couples looking for a memorable day on the water. It suits those wanting a personalized, flexible, and relaxed experience over large, crowded tours. If you enjoy a mix of sightseeing, swimming, and music, or want a unique way to celebrate, this cruise makes a memorable choice.

But if you have mobility issues or are prone to seasickness, it’s worth considering, as the experience involves boat movement and water activities. Also, larger groups will need to inquire about additional arrangements.

FAQ

Is this experience suitable for children?
Since it’s a private cruise with a small group, children are welcome, but the tour recommends no unaccompanied minors and notes that it’s not suitable for those with mobility impairments.

What should I bring?
Bring sunglasses, swimwear, a towel, and sunscreen to stay comfortable and protected during your time on the water.

Can I bring my own drinks?
Yes, alcohol is allowed, and you’re encouraged to bring your own beverages if you prefer. Drinks, snacks, and water toys are included.

How long is the cruise?
The experience lasts approximately 2.5 to 3 hours, giving you plenty of time to relax, swim, and enjoy the scenery without feeling rushed.

What safety measures are in place?
The boat meets the highest safety standards set and maintained by the US Coast Guard. It’s fully licensed, permitted, and insured.

Can I book for a larger group?
Standard pricing is for up to 7 guests, but larger groups (up to 12) can inquire with the provider for arrangements and pricing.

To sum it up, this private sailboat experience on Lake Michigan offers a highly personalized, comfortable way to see Chicago from the water. It’s best suited for those who value exclusivity, flexibility, and a bit of adventure—perfect for special occasions or a memorable day with loved ones. With stunning skyline views, swimming options, and thoughtful amenities, it provides a delightful blend of relaxation and activity, all within a setting that feels both luxurious and approachable. If you’re after an authentic, intimate way to enjoy Chicago’s iconic lakefront, this cruise should be on your list.

You can check availability for your dates here: More Great Tours Nearby