Navy Pier Chicago: Private Sailboat Charter with Captain

If you’re looking to add a touch of elegance and adventure to your Chicago visit, a private sailboat cruise from Navy Pier might just be the perfect fit. We’ve gathered all the details to give you an honest look at what this experience offers—whether you’re celebrating a special occasion, seeking a unique way to see the city’s famous skyline, or simply wanting a peaceful escape on Lake Michigan.

Two things stand out immediately: the personalized nature of the trip and the opportunity to take the helm or jump in the lake for a swim. What we appreciate most is the attention to safety and comfort, with a well-maintained vessel, modern amenities, and a crew committed to hospitality. But, a word of caution—this experience might not be ideal for those with mobility issues or who get seasick easily. Overall, if you’re after a luxurious yet relaxed outing with up to 7 friends or family, this cruise could be a memorable highlight of your Chicago trip.

Key Points

• Private, customizable experience for up to 7 guests, ideal for small groups or intimate celebrations.
• Stunning skyline views of Downtown Chicago, Navy Pier, and the Chicago Lighthouse provide fantastic photo opportunities.
• Flexible activities including sailing, swimming, relaxing on deck, or even taking the wheel.
• Complimentary drinks and snacks are included, with options to BYO for a more personal touch.
• Safety and comfort are prioritized with a licensed, insured vessel meeting US Coast Guard standards.
• Convenient departure point at Navy Pier Marina, with clear meeting instructions provided.

You can check availability for your dates here:

Setting Sail on an Authentic Chicago Experience

Imagine gliding across Lake Michigan, feeling the breeze in your hair as the Chicago skyline slowly unfolds around you. That’s what this private sailboat experience promises—and it delivers. Departing from the newly built Navy Pier Marina, the vessel is modern, meticulously maintained, and equipped with everything needed for comfort and fun.

This isn’t just about sightseeing; it’s about creating a personalized, VIP atmosphere. Whether you prefer to relax in the open cockpit, take control and steer the boat, or jump in the lake to cool off, the experience is tailored to your preferences. The vessel’s amenities—a full kitchen, bathroom, changing room, and a swim platform—ensure that your time on the water is enjoyable and hassle-free.

The Itinerary and What to Expect

Your cruise begins at the Navy Pier Marina, with clear instructions provided beforehand. Once aboard, you’re greeted by a friendly crew committed to making your voyage special. The duration of 2.5 to 3 hours strikes a perfect balance: long enough to soak in the views but not so lengthy that it becomes tiring.

The highlights include cruising along the Chicago Lakefront, with skyline views that are arguably some of the best in the country. The boat’s large open cockpit seating allows everyone to spread out comfortably. As you sail, you’ll enjoy the ability to listen to your favorite tunes via Bluetooth speakers, adding a personal soundtrack to your outing.

One significant feature is the option to anchor in the Chicago Playpen for swimming or floating sessions. The boat comes equipped with a swim platform, noodles, life jackets, and a rinse shower—making it easy to take a quick dip or lounge on the lily pad. Reviewers appreciated that the boat is fully stocked with ice, snacks, and drinks, with no extra fees for fuel or water toys.

The Experience of Sailing in Chicago

Sailing along Lake Michigan offers a different perspective compared to traditional boat tours. Unlike large cruise ships, this vessel allows for a more intimate encounter with the water and skyline. The captain navigates with care, ensuring smooth sailing and safety, while guests can participate by taking the helm if they wish.

People who have taken this cruise often mention how relaxed and exclusive the experience feels. One reviewer wrote, “The staff was attentive without being intrusive, and the views of the city are simply unbeatable.” The ability to swim or just lounge in the sun makes this an ideal summer activity.

Practical Considerations

The boat is fully licensed, permitted, and insured, meeting US Coast Guard standards. This offers peace of mind, especially when you’re considering swimming or drinking alcohol. The cost covers not only the boat and crew but also includes snacks, drinks, and water toys—so what you see is what you get, with no surprise charges for fuel or cleaning.

The experience is designed for a private group of up to 7 guests; larger groups up to 12 are possible but require special inquiry. The departure point is easy to find with provided coordinates, and the meeting instructions are clear.

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Who Will Love This Experience?

If you value personalized service, enjoy water-based adventures, and are looking for a luxurious yet laid-back outing, this cruise ticks all the boxes. It’s perfect for couples celebrating an anniversary, families wanting a fun day on the water, or small groups of friends seeking a memorable Chicago experience.

However, it might not suit those with mobility impairments or who are prone to seasickness. Also, remember to bring essentials like sunglasses, swimwear, a towel, and sunscreen.

Is it Worth the Price?

Considering the all-inclusive nature—with no hidden fees for fuel, water toys, or water—plus the private, customizable experience, many will find this to be good value. It’s more costly than a typical group tour, but the exclusivity and personal touches justify the premium. Plus, the flexibility to bring your own drinks or request catering for an additional fee adds to the versatility.

Summary

This private sailboat charter from Navy Pier offers a blend of luxury, adventure, and intimate connection with Chicago’s iconic skyline. The vessel’s amenities, combined with the freedom to swim, relax, or take control, make it a flexible and memorable option. It’s especially suited for those who want a quiet, personalized experience in a beautiful setting with the safety and comfort of a professionally operated boat.

While it might not be the best choice for guests with mobility issues or those who dislike the water, it hits the sweet spot for travelers looking for a peaceful yet exhilarating way to enjoy Chicago’s Lake Michigan. For the price, the experience offers a high level of service and exclusivity—perfect for creating lasting memories.

FAQ

How long is the cruise?
The cruise lasts between 2.5 and 3 hours, giving you plenty of time to enjoy the lake, scenery, and activities.

Can I bring my own drinks?
Yes, you are welcome to bring your own beverages, and the vessel also provides complimentary drinks and snacks.

Is swimming included?
Yes, you can swim in Lake Michigan from the boat’s swim platform. The boat comes equipped with noodles, life jackets, and a rinse shower.

What is the group size?
The private experience is designed for up to 7 guests, with options for larger groups up to 12 upon inquiry.

Are there any safety restrictions?
The boat is fully licensed, permitted, and insured, meeting US Coast Guard safety standards. Not suitable for people with mobility impairments or seasickness.

What should I bring?
Bring sunglasses, swimwear, a towel, and sunscreen for comfort and protection during your outing.

Is the experience customizable?
Yes, you can choose to relax, swim, take the helm, or listen to your music—it’s all about your preferences on the day.

Whether you’re seeking a romantic escape, a fun family outing, or a special celebration, this private Chicago sailing cruise offers an elegant and authentic way to see the city from the water. With its blend of safety, flexibility, and personal service, it’s an experience that’s easy to recommend—just be sure to book in advance and prepare accordingly.

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