Navy Pier Chicago: Private Sailboat Charter with Captain

If you’re dreaming of seeing Chicago from an entirely different angle, a private sailboat charter along the city’s iconic lakefront might be just what you need. We haven’t personally been aboard this vessel, but based on detailed descriptions and reviews, it promises an intimate, flexible, and uniquely scenic adventure that’s perfect for those seeking a blend of relaxation and active fun.

What we love about this experience is its personalized nature—with up to 7 guests, you can enjoy a customized cruise with your own crew. Plus, the idea of sailing past the downtown skyline while sipping your favorite drinks or jumping into Lake Michigan sounds both refreshing and memorable. The only potential catch? If you’re prone to seasickness or have mobility issues, this might not be your best fit. That said, it’s ideally suited for those who love the water and want a more exclusive Chicago experience away from crowded tourist spots.

If you’re seeking a relaxing afternoon or evening with friends, family, or a romantic partner, this private sailboat cruise could be a highlight of your trip. Here’s everything you need to know to decide if it’s right for you.

Key Points

Private experience: Capacity for up to 7 guests, customizable for larger groups up to 12 with prior inquiry.
All-inclusive: No hidden fees—fuel, drinks, snacks, and water toys are included.
Versatile activities: Sail, swim, jump in the lake, or just relax on deck.
Comfort and amenities: Sky-high views, Bluetooth surround sound, fridge, bathroom, and changing room.
Safety and standards: Fully licensed, insured, and operated by US Coast Guard safety standards.
Flexible booking: Cancel up to 24 hours in advance, with options to reserve now and pay later.

You can check availability for your dates here:

Setting Sail from Navy Pier: What to Expect

The departure point from Navy Pier Marina sets the scene for a seamless start. Once aboard, you’ll be greeted by a well-maintained sailing yacht designed for comfort and style. The vessel boasts a spacious open cockpit seating area, perfect for lounging or socializing, and a swim platform with a rinse shower, noodles, life jackets, and floaties—ideal for those who want to cool off in the lake.

The Itinerary and Highlights

The cruise lasts about 2.5 to 3 hours, which sounds just right for a relaxed yet fulfilling experience. The route primarily focuses on the Chicago Lakefront, offering stunning views of the downtown skyline, Navy Pier, and the Chicago Lighthouse. The boat can anchor in the Chicago Playpen, a popular spot for swimming and floating parties, making the experience more than just sightseeing.

While on the water, guests have the option to:

• Feel the wind in their hair as they sail past the city’s towering buildings, offering an exceptional vantage point usually reserved for boaters and sailors.
• Take the helm—if you’re into sailing, you might get a chance to steer the yacht, adding a dash of adventure to the trip.
• Jump into Lake Michigan—with a swim platform, noodles, and water toys, cooling off becomes an easy and fun part of the journey.
• Relax and soak in the surroundings with the onboard surround sound Bluetooth speakers playing your favorite tunes, creating a personalized soundtrack to your cruise.

Amenities that Enhance the Experience

One of the biggest advantages is the all-inclusive setup. You won’t need to worry about hidden costs; drinks, snacks, ice, and water toys are included, and you’re welcome to bring your own alcohol or snacks for a more personalized touch. The yacht also features a fully stocked kitchen, fridge, bathroom, and changing room—making it comfortable for everyone.

The boat’s modern safety standards and US Coast Guard licensing give peace of mind, especially if you’re bringing kids or want to ensure a worry-free outing. The crew’s attention to detail and hospitality is often praised, with reviews noting the sophisticated service and welcoming atmosphere.

The Value of a Private Yacht Experience

Compared to public boat tours or larger cruise ships, a private sailing cruise offers a level of intimacy and flexibility that’s hard to beat. You control the itinerary to some extent—more time for swimming, relaxing, or even enjoying a private celebration.

Pricing covers everything—fuel, water toys, drinks, and snacks—which means no unexpected extra charges. Plus, since the boat is fully licensed and operated under high safety standards, you can relax knowing that safety is a top priority.

While some reviews mention the possibility of bringing additional provisioning or catering for special occasions, the core experience already offers a well-rounded package, making it an excellent value for those wanting an exclusive, scenic, and enjoyable outing.

More Great Tours Nearby

Who Will Love This Experience?

This cruise is perfect for families, couples, friends, or small groups who want a personalized adventure on Lake Michigan. It’s especially appealing if you enjoy active water activities like swimming and jumping in the lake, or if you simply want to relax on deck with stunning city views.

It’s less suited for those with mobility impairments or who are prone to seasickness, as the experience involves being on open water and some physical activity like swimming.

Final Thoughts

Sailing along Chicago’s skyline on a private yacht strikes a wonderful balance between adventure and relaxation. You gain a unique perspective of the city from the lake, combined with the comfort of a well-equipped vessel and the flexibility of a private group.

Whether celebrating a special occasion, enjoying a leisurely afternoon, or simply escaping the hustle and bustle, this experience offers genuine value. It’s a classy, personalized way to see Chicago from the water—without the crowds, noise, or cookie-cutter tours.

If you’re after authentic, memorable moments on Lake Michigan with a touch of luxe, this private sailboat cruise is worth considering.

FAQs

Can I bring my own drinks and snacks? Yes, you’re welcome to bring your own alcohol, snacks, or beverages, although complimentary drinks and snacks are included in the price.

How long is the cruise? The experience lasts about 2.5 to 3 hours, providing ample time to enjoy sailing, swimming, sunbathing, and taking in the views.

What should I bring? Sunglasses, swimwear, a towel, and sunscreen are recommended for comfort and protection while enjoying the lake and sun.

Are there any restrictions on footwear? High-heeled shoes are not allowed for safety reasons.

Is this experience suitable for children? It’s not recommended for unaccompanied minors and may not be suitable for those with mobility issues or seasickness.

What safety measures are in place? The boat is fully licensed, permitted, insured, and operated under US Coast Guard standards, ensuring a safe outing.

Can I customize the trip? While the route is primarily along the lakefront, flexibility for activities like swimming or relaxing on deck is available. Additional provisioning can be arranged for extra fees.

Where exactly do I meet the captain? Details are provided in your booking email. The coordinates are approximately 41.89215, -87.60748 at Navy Pier Marina.

Is there a cancellation policy? Yes, you can cancel up to 24 hours in advance for a full refund, adding peace of mind to your planning.

Can I book for a large group? Private groups up to 7 are standard, but inquiries for groups up to 12 are welcomed.

This private sailing adventure offers a distinctive, enjoyable way to experience Chicago from a new perspective. It’s a mix of activity and leisure, customized to your group’s pace, making it a memorable highlight for anyone looking to explore Lake Michigan with style.

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