Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago in Chicago
Chicago, United States

Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago

Outty Ranking 70 5.0 · 73 traveler reviews2 hoursFrom $508

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September 2026

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Adults

Age 13 and over

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Age 12 and under

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From, per person$508
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Outty Ranking

70/100

Strongly Recommended. Our proprietary evaluation. How we score

Traveler rating

5.0/5

Based on 73 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.

Quick answer

Is Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago worth booking?

Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago is a 2-hour experience in Chicago, United States, from $508 per person. It scores 70 out of 100 on the Outty Ranking, which we label “Strongly Recommended, based on a 5/5 rating across 73 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.

Outty Ranking
70 / 100
Rating
5/5 (73)
Duration
2 hours
From
$508 per person

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacular sky

What you get

  • Use of Bluetooth speakers
  • Navy Pier Facility Fee
  • All taxes
  • Professional US Coast Guard licensed captain

About this experience

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacular skyline. Make the experience your own. The flexibility of a private charter allows customization of virtually any aspect of the sailing adventure from guest list to music selection to sailing route. Three departure times offered daily. This experience is not meant to be an in-depth guided tour; however, our captain is always happy to point out interesting sights with anecdotes and historical information. Just ask you captain. Looking for a sunset sail, see our other product listing "Come Sailing with us at Navy Pier - Sunset Sail on Lake Michigan". Looking to watch the Navy Pier Fireworks from a private sailing charter, see our other product listing "Come Sailing with us at Navy Pier - Saturday Fireworks Sail". All charters are NON-SMOKING experiences.

What's included

Included

  • Use of Bluetooth speakers
  • Navy Pier Facility Fee
  • All taxes
  • Professional US Coast Guard licensed captain

Not included

  • Gratuities
  • Food and Drinks
  • Parking

What you'll see and do

  1. We will depart from Navy Pier Marina along the north side of Navy Pier. Once the safety briefing is completed and all dock lines have been brought on board, our trip will begin. The itinerary, course/route we are sailing for will depend mostly on the wind direction. However, being that this is a private charter, the itinerary remains very flexible and pretty much at your discretion. So, if you’d like to see a particular landmark or prefer to sail a particular route, just ask our captain and they will be happy to oblige. If, instead, you’d prefer to leave all of the decision up to the captain, no problem. Our captain will be happy to take you for an enjoyable sunset sail on Lake Michigan during which you will sail in close proximity to some, or all, of the landmarks listed in the itinerary below.

    120 minutes here · Admission included

  2. Navy Pier

    One of the most recognized landmarks along Chicago’s lakefront, Navy Pier is also one of the most and visited tourist destinations in Chicago. Sailing passed the east end we’ll have a great view of the Grand Ballroom. This would be another perfect time to snap some selfies or capture a stunning architectural photo. Opened to the public in 1916, Navy Pier has played many roles during its lifetime including an important role during WWII. This piece of Chicago is definitely more than just a photo op!

    Pass by without stopping

  3. Chicago Skyline

    One of the most beautiful waterfront cities in the world, Chicago’s magnificent skyline is best viewed from the water. There are too many stories to be told about the amazing architecture, landmarks, and engineering feats accomplished in Chicago. Which ones you hear are up to you. Again, this is your private charter and you set the tone for the trip. If you prefer to just visit with friends and loved ones, no worries at all. Our captains are happy to the role of captain, guide, or both. Come Sailing and let us show you the city we love.

    Pass by without stopping

  4. Adler Planetarium

    Sitting on the northeast corner of Northerly Island is the iconic dome of the Adler Planetarium. Built in 1930, this picturesque public museum dedicated to the study of astronomy and astrophysics a popular location for wedding photos. From the Lake, we get to see a side of this marvelous structure that most visitors never think to investigate: the lakeside! This is where you will find the Doane Observatory which has a large telescope available to the public.

    Pass by without stopping

  5. Soldier Field

    Opened in 1924, Soldier Field, known today as the home of the Chicago Bears, has played host to a variety of interesting and historical events. Even though the stadium has changed drastically over the years, the original colonnades can still be seen from our vantage point on the water.

    Pass by without stopping

  6. Clarence F. Buckingham Fountain

    On July 6, 1959, a small barge ferried Queen Elizabeth II from the HMY Britannia anchored outside of Monroe Harbor to the aptly named Queen’s Landing for a 13-hour royal visit spectacular. As we pass this historic site Buckingham Fountain comes into view. (Pro Tip: this is a great time for a photo op.) Buckingham Fountain, one of the world’s largest fountains, was designed as a focal centerpiece for Grant Park. According to the Chicago Park District website, John Philips Souza himself conducted his band in the playing of “Pomp and Circumstance” before an audience of 50,000 people during the fountain’s dedication in August 1927. Contrary to conventional wisdom, Buckingham fountain is not related to Buckingham Palace or the Royal Family. The fountain was actually donated by Chicago art patron and philanthropist, Kate Buckingham in memorial honor of her brother Clearance Buckingham.

    Pass by without stopping

Where it starts and ends

Meeting point

Chicago

We operate from the new Navy Pier Marina located along the north side of Navy Pier. Please gather outside of Navy Pier Marina - Gate D and then text/call us to tell us that you are here. We will welcome you to the marina and escort you to the sailboat.

Hotel pickup

No pickup: everyone meets at the start point.

Ends at

We operate from the new Navy Pier Marina located along the north side of Navy Pier. Please gather outside of Navy Pier Marina - Gate D and then text/call us to tell us that you are here. We will welcome you to the marina and escort you to the sailboat.

Before you book

Cancellation
For a full refund, cancel at least 24 hours before the scheduled departure time.
Languages
en
Ticket
Mobile Only
Runs on
Every day
Group size
Up to 15 travelers per booking
Operated by
Come Sailing, Inc.

Know before you go

  • Public transportation options are available nearby
  • Suitable for all physical fitness levels
  • NO SMOKING - All charters are NON-SMOKING. Use of any tobacco products, cigars, pipes, cigarettes, e-cigarettes, vapor devices, etc. are strictly prohibited. Use of any of these products may result in a non-refundable, early termination of your charter and the assessment of a cleaning fee.
  • CONSUMPTION OF ALCOHOL - Customers and guests may bring and consume reasonable amounts of alcoholic beverages within the bounds of Illinois State law.
  • NO GLASS ON BOARD - Glass containers are prohibited. Please do not bring them. Wine and Champagne bottle are permitted as long as they remain secure in a protective container during charter. Please bring plastic cups for drinking.
  • CUSTOMER/GUEST BEHAVIOR - Customers and guests are expected to conduct themselves in an appropriate manner. Inappropriate behavior will not be tolerated. Any behavior determined by the captain to be inappropriate (lewd, offensive, unsafe, etc.) may result in a non-refundable, early termination of your charter.
  • WEAPONS ARE STRICTLY PROHIBITED - Weapons on any kind are strictly prohibited! Guns, knives, or weapons of any kind are NOT allowed on board our vessels at any time. Bringing any of these prohibited items aboard may result in a non-refundable, early termination of your charter.
  • ANIMALS ARE PROHIBITED - Unfortunately, we cannot accommodate animals of any type.
  • SWIMMING MAY BE PERMITTED - Swimming may be permitted on charters of 3 hours or longer. Swimming is not guaranteed and is at the captain's discretion. If swimming is deemed permissible by the captain, every passenger on board will be required to sign a waiver & release prior to swimming. Swimming will not be allowed after the departure time of our Sunset Sail scheduled for that same day. SWIMMING IS AT YOUR OWN RISK!
  • FOOD AND BEVERAGE - Food and beverages may be consumed on deck. Please clean up any spilled food or beverage and take your garbage with you. A cleaning fee may be assessed for excessive spillage.
  • SEASICKNESS/MOTION SICKNESS - Any person that experiences seasickness must remain on deck. The cabin area below deck is NOT an appropriate place for any person to deal with seasickness. A cleaning fee will be assessed for any person vomiting anywhere in the below deck cabin area of the sailboat, including the “head”/bathroom.
  • GALLEY STOVE AND SINK - The galley stove onboard our sailboat is NOT for use by customers. The sinks on board our boats drain directly into the lake and are NOT intended for food prep nor for disposing of unwanted items. None of the sinks have garbage disposals. Please do NOT treat our sinks like you treat your kitchen sink. They are NOT the same.
  • CLEANING FEES - Cleaning fees, if applicable, will be equivalent to the standard, full price of your charter.
  • TERMINATION OF CHARTER - The captain reserves the right to cancel a charter at any time for reasons of weather, mechanical failure, or safety. Charters will be rescheduled at the customer’s convenience. A refund will be offered if rescheduling cannot be agreed upon.
  • LATE ARRIVALS - The late arrival of customers and guests may result in a shortened charter sail without refund nor adjustment to price.
  • BOOKING ERRORS - We reserve the right to cancel reservations that are the result of incorrect pricing/availability due to malicious acts or software/website errors.
  • CONSENT TO BE FILMED/PHOTOGRAPHED - Boarding our sailboats is your implied consent to be filmed, photographed, and recorded. Furthermore, by boarding any of our sailboats you are granting our company, its agents, successors, assignees and affiliates, and their respective employees, officers, directors, shareholders, and representatives the right and permission to use such film, photographs, and recordings of your voice, image, and likeness for the purpose of promoting our company and its related services. You further agree that you will not receive any financial compensation or cash payment for the rights or permissions granted by you. In such case that you are the parent or guardian of any minor child that has accompanied you aboard our sailboat, you further consent to the foregoing on behalf of that minor child.

Photos

Relaxing on the bow with friends.From the bow. Plenty of room on the foredeck for relaxing with friends and family.Our sailboat, Bernard, sailing at sunset.Sitting on the foredeck taking in a relaxing sail.The Chicago Light. A great subject for your photos.Four Mile Crib. Come Sailing and see a bit of Chicago history.

What travelers are saying

Outty’s summary of the themes that recur across 73 traveler reviews. Written by us, not quoted from reviewers.

Knowledge and storytelling

3 mentions

Reviewers describe the commentary as informative rather than scripted.

Traveler reviews

73 verified traveler reviews for Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago. Ratings and reviews provided by Viator and Tripadvisor.

5 star
73
4 star
0
3 star
0
2 star
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0
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rusty_stein · August 2026

A relaxing morning sail on Lake Michigan

Captain Ulysses was great. Fun, friendly, and very responsible. Good communication leading up to the trip. A beautiful way to see the Chicago skyline.

via Tripadvisor

Jennifer_G · July 2026

A+! We loved every minute.

We LOVED our sailing excursion with Captain Ulysses! 6 of us went during a girls weekend, and it was the absolute highlight of our trip. Captain Mike and Captain Ulysses got us on board right on time, and we enjoyed two hours of sailing with great wind and a ton of excitement. If you’re considering booking, DO IT. As a group of moms, we tend to spend our girls trips catching up and reminiscing, and not always making NEW fun memories together. This was exactly what we needed, and we’ll remember this outing forever. We were begging to buy out the next hour, but someone already had it booked. We’d absolutely do it again! Thank you for a great time!

via Viator

E7290VJkristina · July 2026

Wonderful Chicago boat tour! 5 star!

Wonderful Chicago excursion! Our guide was so personable and accommodating! Great way to see the Chicago skyline and enjoy some relaxation. Highly recommend!

via Tripadvisor

Laura S · September 2025

The Perfect Afternoon

My husband and I had a wonderful cruise during our trip to Chicago. Seeing the city from the water was a unique twist on the typical tours and absolutely beautiful. The sailboat was pristine and our captain was incredibly engaging, answering our endless questions both about the city’s history and sailing. This was a perfect way to spend an afternoon. I would absolutely recommend this tour!

via Tripadvisor

Polly_M · September 2025

Fantastic voyage

Wonderful way to experience the Chicago skyline Captain Mike was awesome, time flew by and we want to do it again.

via Viator

Good to know

Duration
2 hours
Free cancellation
Up to 24h before
Minimum age to book
All ages
Availability
Bookable today
Runs on
Every day
Price range
$508 to $567
Hotel pickup
No pickup, meet at start point
Booked in 30 days
26
Verdict
Strongly Recommended

Why this scores 70

The Outty Ranking is a weighted composite. Here is how this experience performed on each component.

Traveler sentiment (30% weight)94
Review evidence (18% weight)55
Booking momentum (14% weight)49
Value for money (12% weight)0
Listing quality (10% weight)100
Local standing (8% weight)89
Booking flexibility (8% weight)100

Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago: questions travelers ask

Practical detail on this experience, plus the wider planning questions for Chicago.

How much does Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago cost?

+

Prices start at $508 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Chicago usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.

How long does Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago take?

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Plan for about 2 hours from start to finish, not counting travel to the meeting point. Most travelers leave another 30 minutes on either side so the rest of the day in Chicago is not rushed.

Is Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago worth it?

+

It holds an Outty Ranking of 70 out of 100, which we label "Strongly Recommended". That score blends traveler sentiment (5/5 across 73 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable last minute in Chicago, and how flexible the cancellation terms are.

Can I cancel or reschedule Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago?

+

Yes. Cancel free up to 24 hours before the start time for a full refund. Inside that window the booking is non-refundable, and no-shows are not refunded.

Is Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago suitable for kids and families?

+

Yes, all ages are welcome. Families should still weigh the 2-hour running time, and strollers are easier on the earlier, quieter departures.

How far in advance should I book Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago?

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Around 26 people booked this in the last 30 days, so popular slots go early. Two to three weeks ahead is comfortable in shoulder season, while summer weekends and holidays in Chicago can sell out a month out. Same-day spots do open up when other travelers cancel, so it is worth checking if you are already in town.

What should I bring or wear?

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Bring photo ID, your booking confirmation on your phone, a refillable water bottle and comfortable shoes. Dress for the weather in Chicago and add a light layer if any part of the 2-hour experience runs outdoors or after sunset.

Where does Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago start and how do I get there?

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The exact meeting point and directions are on your voucher once you book, and they sit in central Chicago within reach of public transport. Arrive 15 minutes early: late arrivals are treated as no-shows by most operators.

What are the best things to do in Chicago?

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Chicago's signature experience is still the architecture boat cruise, and the difference between the docent-led originals and the party-boat imitators is the single biggest quality gap in the city. Beyond the river: gangster history walks, Art Institute access, deep-dish and hot-dog crawls, and skydeck timed entry. Outty Ranking leans on guide credentials and how consistently the promised route runs. On Outty we rank every Chicago experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include Original Chicago Architecture Interiors Tour: Dazzling Interiors, Chicago Murder Mystery Tour, Chicago Favorites Ultimate Food and Walking Tour. The city page groups everything into most popular, highest reviewed, last minute and family-friendly so you can build a day around what actually delivers.

When is the best time to visit Chicago?

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May to October. Winter cruises stop running when the river ices. Booking patterns follow the same curve: prices and queues climb in peak weeks, while shoulder season gives you better availability on the top-ranked experiences and more room to change plans.

How many days do you need in Chicago?

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Three full days covers the headline sights without sprinting. A workable rhythm is one anchor experience each morning, such as this one, an unhurried afternoon in a single neighborhood, then a food or nightlife booking in the evening. Five days lets you add a day trip outside the city.

Do I book through Outty or through the operator?

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Outty ranks and explains the experiences, then hands you to Viator to complete the booking with the operator directly. The price is the same as booking on Viator yourself, and Outty earns an affiliate commission on the referral, which is how the rankings stay free to read.

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