Private Sailing on Beautiful Lake Michigan – Navy Pier, Chicago

Taking to Lake Michigan for a private sailing experience offers a unique and peaceful perspective of Chicago that few visitors get to enjoy. For about $567 per group, up to 6 guests can indulge in this 2-hour tailored tour, departing from Navy Pier. Guided by a US Coast Guard licensed captain, the trip combines scenic views, flexibility, and the chance to get involved at the helm. This tour is especially suited for those seeking a personalized, relaxed outing with the freedom to choose start times and enjoy music via Bluetooth speakers.

While food and drinks are not included, the tour’s core appeal lies in its customizable itinerary and outstanding views of the Chicago skyline. It’s perfect for celebrating special occasions, enjoying a laid-back afternoon, or simply experiencing Lake Michigan from a new vantage point. The tour’s high rating of 5.0 out of 5 with 70 reviews confirms its popularity and quality.

Key Points

• Private, customizable 2-hour sailing tour for groups up to 6 people
• Departs from Navy Pier Marina, Chicago, with flexible start times
• Expert US Coast Guard licensed captain guides your journey
• Enjoy stunning skyline views and landmarks like Soldier Field and Adler Planetarium
• Use Bluetooth speakers for your playlist during the sail
• No food or drinks included, but alcohol is permitted in moderation

Departure from Navy Pier Marina: The Starting Point of Your Chicago Water Adventure

This private sailing tour departs from Navy Pier Marina, located along the north side of Navy Pier, one of Chicago’s most iconic landmarks. After a brief safety briefing, the captain takes control, and the voyage begins. The marina’s location offers a convenient meeting point for visitors staying in or near downtown Chicago. The facility fee and all taxes are included in the price, ensuring a smooth start to your experience.

The group size is limited to 6 guests, creating an intimate atmosphere. The mobile ticket process adds convenience, allowing for easy check-in and flexible scheduling. The tour is designed to be accessible and enjoyable for most travelers, with near public transportation options nearby.

Highlights of the Chicago Skyline from the Water

Sailing past Navy Pier, travelers enjoy panoramic views of the Chicago skyline, including the Grand Ballroom, the Adler Planetarium, and Soldier Field. These landmarks are visually impressive when seen from the lake and serve as a dramatic backdrop for photographs. The views from the water reveal architectural details and cityscapes that are often missed from land.

The skyline is described as magnificent and best appreciated from the lake, providing a sense of scale and grandeur. The tour’s route is fully customizable, allowing your group to focus on areas of special interest. The captain shares insights into Chicago’s architecture and history, making the experience both scenic and educational.

Iconic Stops Along Lake Michigan: Navy Pier and Beyond

The tour passes Navy Pier, one of Chicago’s most visited tourist destinations, offering a great view of the Grand Ballroom and surrounding attractions. From there, the sailboat heads toward the east end of the pier for unobstructed views of the city’s waterfront.

Other significant sights include the Adler Planetarium, sitting on the northeastern corner of Northerly Island, known for its distinctive dome structure. The stadium of Soldier Field, opened in 1924 and home to the Chicago Bears, is another prominent landmark visible from the water. Passing Queen Elizabeth II’s historic ferrying barge during a royal visit adds a touch of historical intrigue to the route.

Each stop or view can be tailored based on your group’s preferences, with the captain providing commentary on the landmarks and their stories.

Flexibility and Customization: Craft Your Perfect Sailing Trip

A key feature of this tour is its fully customizable itinerary. Travelers can select from several start times to fit their schedules, making it suitable for both morning and afternoon adventures. The captain can adapt the route, emphasizing scenic views, landmarks, or a relaxed cruise depending on your desires.

This flexibility makes the experience ideal for celebrating special events like birthdays or anniversaries or simply enjoying a peaceful day on the lake. Given the positive reviews, the captain’s ability to answer questions and share Chicago’s stories enhances the personal feel of the tour.

Bluetooth Music and Onboard Comforts

The sailboat is equipped with Bluetooth speakers, allowing your party to set a playlist and enhance the mood of the trip. The boat itself is clean and comfortable, with enough space for everyone to relax and enjoy the surroundings. This small onboard touch helps create a personalized ambiance that elevates the experience beyond just sightseeing.

Since food and drinks are not included, guests often bring their own beverages, with alcohol permitted in moderation, as long as it’s reasonably consumed. Bringing plastic cups for drinks is recommended, and all cleanup should be done by your group to avoid extra fees.

Practical Guidelines and Rules for a Smooth Trip

The tour maintains strict policies to ensure safety and comfort. No smoking, no glass containers, and no weapons or animals are allowed onboard. Swimming may be permitted if the captain deems it safe and the trip is at least 3 hours, but this is at the captain’s discretion and involves signing a waiver.

Guests are asked to conduct themselves appropriately, with inappropriate behavior possibly leading to early termination of the trip without a refund. Late arrivals may result in shortened sails, so punctuality is advised. The captain reserves the right to cancel the trip due to weather or mechanical issues, with rescheduling or full refunds offered.

Experienced Guides and Friendly Captains

Multiple reviews highlight the knowledgeable and friendly captains, such as Captain Mike and Captain Ulysses. They are praised for their capability, patience, and willingness to answer questions about sailing, Chicago, and local landmarks.

The captain’s storytelling adds a personal touch, making the trip both an educational and enjoyable experience. Many reviews mention how the guides make everyone feel comfortable and engaged, contributing heavily to the tour’s high satisfaction ratings.

The Experience of a Lifetime on Lake Michigan

This private sailing trip offers more than just sightseeing—it’s an opportunity to relax, take in breathtaking views, and enjoy Chicago from a peaceful vantage point. The intimate setting and customizable route allow for a tailored experience, perfect for celebrating a special occasion or simply escaping the city hustle.

Most reviewers agree that the views of the downtown skyline from the water are spectacular, and the friendly, professional captains make all the difference. The 2-hour duration strikes a good balance between a leisurely cruise and a manageable outing for most schedules.

Who Will Love This Chicago Sailing Tour

This tour suits small groups seeking a personalized, quiet escape on Lake Michigan. It’s ideal for special celebrations, romantic getaways, or family outings. The flexibility, scenic views, and knowledgeable guides make it a rewarding activity for those interested in Chicago’s architecture and lakefront landmarks.

While food and drink are not provided, bringing your own alcohol and music helps craft a relaxed, enjoyable atmosphere. The capacity of 6 guests ensures an intimate setting, free from crowded tour boats or large groups.

Final Thoughts on the Chicago Private Sailing Experience

For a calm, scenic, and customizable way to see Chicago’s skyline and waterfront, this private sailing tour stands out. The expert captains, stunning views, and flexible itinerary make it a popular choice, evidenced by a perfect 5.0 rating and excellent reviews. While it’s best suited for those who enjoy relaxed outings and don’t mind bringing their own refreshments, the overall experience offers a genuinely unique perspective of Chicago from the water.

This 2-hour sail is a peaceful alternative to busy boat tours, perfect for creating lasting memories with friends or family in one of America’s most beautiful waterfront cities.

Frequently Asked Questions

How long is the sailing tour?
The tour lasts approximately 2 hours.

What is the maximum group size?
Up to 6 guests can participate in this private tour.

Where does the tour start?
The tour departs from Navy Pier Marina at 801 E Grand Ave, Chicago.

Can I bring my own food and drinks?
Food and beverages are not included, but you may bring alcohol in moderation and plastic cups for drinks.

Is the trip suitable for children?
Most travelers can participate; however, children should be supervised, and the tour involves being on a boat for two hours.

What if the weather is bad?
The captain reserves the right to cancel due to poor weather, in which case a full refund or rescheduling is offered.

Can I swim during the tour?
Swimming may be permitted on trips of 3 hours or longer but is at the captain’s discretion and requires signing a waiver.

Are there any restrictions on smoking or weapons?
Yes, smoking and weapons are strictly prohibited on board.

Is there parking available at the departure point?
Parking is not included; guests should plan accordingly.

How do I book or cancel?
Booking is confirmed instantly, with free cancellation available up to 24 hours in advance.