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Private Lake Michigan Sailing Charter and Sightseeing Tour of Chicago

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Chicago, United States
Private Lake Michigan Sailing Charter and Sightseeing Tour of Chicago
Likely to Sell OutLikely to Sell Out

From USD427.28 per group (up to 6)

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Free cancellation
Up to 24 hours in advance. Learn more
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Safety measures
icon2 hours  (approx.)
Mobile ticket
iconOffered in: English
Good for avoiding crowds


If you’ve ever dreamed of sailing away on your own private sailboat, this is the perfect excursion for you. You and up to five other invited guests will have the exclusive use of a sailboat, complete with captain and crew for the duration of your tour. Sail on Lake Michigan and enjoy the sights of Chicago’s striking skyline. If you want, you could even take a turn at the helm.
  • The choice is yours: morning, afternoon or evening departures available
  • BYOB, but no glass containers. Keep cool with included ice and fridge
  • Itineraries are fully customizable to your group’s interests
  • Bring a Blue tooth enabled device to get your tunes playing
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Professional US Coast Guard licensed captain
Use of Bluetooth speakers
All applicable taxes
Food and Drinks
Come Sailing, Inc. , Monroe Harbor, Chicago, IL 60603, USA

From the northeast corner of Lake Shore Dr. and Monroe St. follow the lakefront trail to the north and continue along the harbor’s edge as the trail bends to the east. Our boat will meet you along the Monroe Harbor wall east of the cement pier (aka the pump out dock). Our boat’s name is BERNARD.

This activity will end right where it started.
  • Confirmation will be received at time of booking
  • 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.
  • Not wheelchair accessible
  • Near public transportation
  • CONSENT TO BE FILMED/PHOTOGRAPHED - Boarding any sailboats operated by Come Sailing, Inc. is your implied consent to be filmed, photographed, and recorded. Furthermore, by boarding any of our sailboats you are granting Come Sailing, Inc., their 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 Come Sailing, Inc. 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.
  • COVID-19 FACE MASKS ARE OPTINAL - MASK FREE SAILING IS HERE! New for 2022, face masks are OPTIONAL. Wear them or not, the choice is yours. Our captains and crew are not required to wear face masks. However, if it would make you feel more comfortable, please let the captain know and they will be more than happy to wear face masks during your charter.
  • COVID-19 SOCIAL DISTANCING - This is a private charter for you and your guests only. Social distancing is your responsibility and at your discretion within your group. There is plenty of space on board our sailboats to spread out and maintain appropriate social distances.
  • COVID-19 SICK PEOPLE SHOULD STAY AT HOME - All passengers are required to self-diagnose their health status before boarding and let us know if they are not feeling well. PLEASE STAY AT HOME IF ANY OF THESE CONDITION APPLY: SICK – If you are sick or not feeling well. SYMPTOMATIC – If, in the last 5 days, you have experiences symptoms related to COVID-19, the flu, or any other potentially contagious disease.
  • COVID-19 ACCESS TO CABIN AND RESTROOMS - The fun is up on deck sailing! Not hanging out below deck in the cabin! So, please minimize your time below deck in the cabin. We also ask that no more than one person goes down below into the cabin at a time. There is a restroom on board each boat. However, the restrooms are small, and toilets on a boat do NOT work the same way your toilets work at home. Please ask the captain and crew before using the restroom. We strongly encourage you to use the public restrooms on shore prior to boarding.
  • COVID-19 FOOD, WATER, AND ICE - We will have bottles of water available. However, we encourage you to bring your own beverages and help us reserve our water for emergency hydration. We will provide a small cooler in which passengers may store items to keep them cold. Food, beverage, and ice storage is limited to provided cooler. Please plan accordingly.
  • COVID-19 POLICY UPDATES AND CHANGES - The above policies are subject to change without notice in response to changes in status of the COVID-19 pandemic and in order to comply with new or changing guidance from the Centers for Disease Control and Prevention, Illinois Department of Public Health, Cook County Department of Public Health, and Chicago Department of Public Health.
  • Most travellers can participate
  • This is a private tour/activity. Only your group will participate
  • OPERATED BY Come Sailing, Inc.
You can cancel up to 24 hours in advance of the experience for a full refund.
  • For a full refund, you must cancel at least 24 hours before the experience’s start time.
  • If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.
  • Any changes made less than 24 hours before the experience’s start time will not be accepted.
  • Cut-off times are based on the experience’s local time.
  • This experience requires good weather. If it’s cancelled due to poor weather, you’ll be offered a different date or a full refund.

Learn more about cancellations.

The answers provided below are based on answers previously given by the tour provider to customers’ questions.
What is the policy on sanitisation during Private Lake Michigan Sailing Charter and Sightseeing Tour of Chicago?
A:The policy on sanitisation is:

  • Hand sanitiser available to travellers and staff
See all safety measures taken by Private Lake Michigan Sailing Charter and Sightseeing Tour of Chicago.
What is the social distancing policy during Private Lake Michigan Sailing Charter and Sightseeing Tour of Chicago?
A:The policy on social distancing is:

  • Contactless payments for gratuities and add-ons
See all safety measures taken by Private Lake Michigan Sailing Charter and Sightseeing Tour of Chicago.

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17 reviews
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Reviews by Viator travellers

Showing 1-9 of 17 reviews
Highly recommend!
, Aug. 2021
Mike was excellent, the boat was large, immaculate and well maintained. Wind was great and we all enjoyed the sail.
Fun time with Grandaughters
, Aug. 2021
Such a relaxing 2 hours on the water. The views were amazing. Captain Mike was great. He would answer questions but didn’t talk to much. He seemed as relaxed as we were and that made for a great time for two grandparents to spend with four granddaughters aged 9- 14.
Great views and relaxing break from the city
, Jul. 2021
Beautiful and peaceful day on the lake. It was such a neat thing to experience in the middle of a big city trip.
1 traveller found this review helpful
Great Lakes sailing experience with city skyline
, Jul. 2021
Experienced captain And crew. Knew how to “read” the lake for a safe abs fun adventure! Accommodating, on time, and relaxing-effortless experience! Great way to wrap up the holiday weekend. Highly recommended.
icon Response from Host , Jul. 2021
Thank you for sailing with us! We pride ourselves on fun, safe sailing! Feedback is always appreciated and is particularly fun to hear when our customers have such a great time on the water. Hope to see you again soon! Thank you, Capt. Mike
Best view in Chicago
, Jul. 2021
We had family visiting for the holiday and had the best time. Great views and Capt. Mike was so friendly and knowledgeable. We will definitely sail again.
icon Response from Host , Jul. 2021
Thanks Debbie_G for sailing with us! We love hearing from our customers! It makes us proud when we hear how much fun our customers are having on the water with us! Thank you, Capt. Mike
Great experience
, May 2021
Mike was a great captain he seemed very knowledgeable and the boat was in great condition. Overall great experience.
icon Response from Host , Jul. 2021
Thank you for sailing with us Andrea_A! And thank you for taking the time to write a review! We appreciate hearing about our customers' experiences while sailing with us! Capt. Mike
Great choice!
, Jul. 2020
Very pleased with the entire experience. Will definitely do it again! A small group of us (6) had an awesome time on the Lake with wonderful views of the Skyline & Navy Pier. Fantastic experience for both locals and tourists.
Fantastic Outting for Teams
, Jun. 2019
This trip was awesome. The captian was fabulous, kind, and funny. We had a team outting with 5 people. The lake was beautiful and we felt extremely safe. We'd highly recommend this cruise to anyone looking to enjoy views of the city from the water!
1 traveller found this review helpful
Excelente experiencia
, Jul. 2020
Una experiencia inolvidable. Vale la pena la inversión de el dinero. El capitán muy respetuoso y muy amable. Lo recomiendo 100%

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