Tours and Tickets

Private Sunset Sail on Lake Michigan with Breathtaking Views of Chicago provided by Come Sailing, Inc.

Private Sunset Sail on Lake Michigan with Breathtaking Views of Chicago

Private Sunset Sail on Lake Michigan with Breathtaking Views of Chicago
5
Book in advance
from
£315.57
per group (up to 6)
Free Cancellation up to 24 hours in advance
Reserve now & pay later: Save your spot free of charge with flexible booking.
About
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.  All charters are NON-SMOKING experiences.
Know before you go
  • Duration: 2h
  • Mobile tickets accepted
  • Instant confirmation
Cancellation policy
  • For a full refund, cancel at least 24 hours in advance of the start date of the experience.
Available languages
English
Know before you go
  • Duration: 2h
  • Mobile tickets accepted
  • Instant confirmation
Available languages
English
Cancellation policy
  • For a full refund, cancel at least 24 hours in advance of the start date of the experience.
Need help booking?
Call the number below and use the product code: 46250P2
Call +44 12 2492 8241
Important information
Inclusions
  • Professional US Coast Guard licensed captain
  • Use of Bluetooth speakers
  • All applicable taxes
  • Entry/Admission - Chicago
Exclusions
  • Gratuities
  • Food and Drinks
  • Parking
Duration
2h
Departure details
  • Come Sailing, Inc., Monroe Harbor, Chicago, IL 60603, USA From the intersection of Monroe St. and Lake Shore Dr., walk northeast to the water’s edge and continue walking along the north side of the harbor as it curves first to the east and then again to the north. Our boat will meet you at spot #4 in the yellow stripe along the “Monroe Charter Wall”.
Additional information
  • 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 IS PROHIBITED - Swimming is not allowed on our Sunset Sails.
  • 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.
  • GIFT CERTIFICATES/VOUCHERS - Gift Certificates may not be redeemed for cash. Gift certificates may be used to purchase products and services offered by Come Sailing, Inc. The terms “gift voucher” and “gift certificate” have the same meaning and are used interchangeably throughout our website.
  • LATE ARRIVALS - The late arrival of customers and guests may result in a shortened charter sail without refund nor adjustment to price.
  • Not wheelchair accessible
  • Near public transportation
  • 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 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 MASK POLICY - MASK FREE SAILING FOR VACCINATED PASSENGERS – That’s right! Fully vaccinated passengers with proof of vaccination are NOT required to wear a face covering. You MUST provide proof of vaccination to sail mask free. Don’t worry, there will be opportunities for unvaccinated passengers to remove their face masks and enjoy the fresh air as well. The captain will explain in detail where and when those passengers may remove their masks. With the exception noted above, passengers are REQUIRED to wear secure fitting face masks covering both their nose and their mouth. Our captains and crew are all fully vaccinated. As such, they are not required to wear face masks but will do so upon request. Masks are not provided, please bring your own. Passengers will immediately don face masks upon request from the captain or crew. If you are unable or unwilling to either provide proof of vaccination or wear a face mask, please do not book a charter with our company.
  • COVID-19 SOCIAL DISTANCING POLICY - There is plenty of space on board our sailboats. Please spread out and maintain appropriate social distancing from the captain and crew when able to do so. Social distancing within your own group is your responsibility and at your own discretion. While maneuvering and sailing our boats, it may be necessary for the captain and crew to be in close proximity to you. As a result, the captain may request passengers to temporarily move to another part of the boat to maintain appropriate social distancing. Thank you in advance for your cooperation.
  • COVID-19 SICK PEOPLE SHOULD STAY AT HOME POLICY - 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 14 days, you have experiences symptoms related to COVID-19, the flu, or any other potentially contagious disease. EXPOSURE – If, in the last 14 days, you have been exposed (or potentially exposed) to persons symptomatic of, or diagnosed with COVID-19, the flu, or any other potentially contagious disease.
  • COVID-19 LIMITED ACCESS TO CABIN AND RESTROOMS - Due to COVID-19, access to the cabin area and spaces below deck is extremely limited and by permission only. Permission must be requested of and granted by the captain each time a passenger wishes to access the cabin area and spaces below deck. No more than one passenger will be granted access to the cabin area and spaces below deck at any given time. Access to the cabin area and spaces below deck will be granted solely for use of the head (restroom). A secure fitting face mask must be worn by a passenger the entire time they are in the cabin area and spaces below deck. Food, drinks, and personal belongings are not allowed in the cabin area and spaces below deck. We strongly encourage the use of public restrooms on shore prior to boarding.
  • COVID-19 FOOD, WATER, AND ICE POLICY - 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 on deck in which passengers may store items to keep them cold. Due to COVID-19, the refrigerator in the cabin area is restricted to use by the captain and crew only. Food, beverage, and ice storage is limited to the on-deck cooler. Please plan accordingly.
  • Most travellers can participate
  • This experience requires good weather. If it’s cancelled due to poor weather, you’ll be offered a different date or a full refund
  • This is a private tour/activity. Only your group will participate
Inclusions
  • Professional US Coast Guard licensed captain
  • Use of Bluetooth speakers
  • All applicable taxes
  • Entry/Admission - Chicago
Exclusions
  • Gratuities
  • Food and Drinks
  • Parking
Departure details
  • Come Sailing, Inc., Monroe Harbor, Chicago, IL 60603, USA From the intersection of Monroe St. and Lake Shore Dr., walk northeast to the water’s edge and continue walking along the north side of the harbor as it curves first to the east and then again to the north. Our boat will meet you at spot #4 in the yellow stripe along the “Monroe Charter Wall”.
Duration
2h
Return details
  • Returns to original departure point
Additional information
  • 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 IS PROHIBITED - Swimming is not allowed on our Sunset Sails.
  • 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.
  • GIFT CERTIFICATES/VOUCHERS - Gift Certificates may not be redeemed for cash. Gift certificates may be used to purchase products and services offered by Come Sailing, Inc. The terms “gift voucher” and “gift certificate” have the same meaning and are used interchangeably throughout our website.
  • LATE ARRIVALS - The late arrival of customers and guests may result in a shortened charter sail without refund nor adjustment to price.
  • Not wheelchair accessible
  • Near public transportation
  • 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 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 MASK POLICY - MASK FREE SAILING FOR VACCINATED PASSENGERS – That’s right! Fully vaccinated passengers with proof of vaccination are NOT required to wear a face covering. You MUST provide proof of vaccination to sail mask free. Don’t worry, there will be opportunities for unvaccinated passengers to remove their face masks and enjoy the fresh air as well. The captain will explain in detail where and when those passengers may remove their masks. With the exception noted above, passengers are REQUIRED to wear secure fitting face masks covering both their nose and their mouth. Our captains and crew are all fully vaccinated. As such, they are not required to wear face masks but will do so upon request. Masks are not provided, please bring your own. Passengers will immediately don face masks upon request from the captain or crew. If you are unable or unwilling to either provide proof of vaccination or wear a face mask, please do not book a charter with our company.
  • COVID-19 SOCIAL DISTANCING POLICY - There is plenty of space on board our sailboats. Please spread out and maintain appropriate social distancing from the captain and crew when able to do so. Social distancing within your own group is your responsibility and at your own discretion. While maneuvering and sailing our boats, it may be necessary for the captain and crew to be in close proximity to you. As a result, the captain may request passengers to temporarily move to another part of the boat to maintain appropriate social distancing. Thank you in advance for your cooperation.
  • COVID-19 SICK PEOPLE SHOULD STAY AT HOME POLICY - 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 14 days, you have experiences symptoms related to COVID-19, the flu, or any other potentially contagious disease. EXPOSURE – If, in the last 14 days, you have been exposed (or potentially exposed) to persons symptomatic of, or diagnosed with COVID-19, the flu, or any other potentially contagious disease.
  • COVID-19 LIMITED ACCESS TO CABIN AND RESTROOMS - Due to COVID-19, access to the cabin area and spaces below deck is extremely limited and by permission only. Permission must be requested of and granted by the captain each time a passenger wishes to access the cabin area and spaces below deck. No more than one passenger will be granted access to the cabin area and spaces below deck at any given time. Access to the cabin area and spaces below deck will be granted solely for use of the head (restroom). A secure fitting face mask must be worn by a passenger the entire time they are in the cabin area and spaces below deck. Food, drinks, and personal belongings are not allowed in the cabin area and spaces below deck. We strongly encourage the use of public restrooms on shore prior to boarding.
  • COVID-19 FOOD, WATER, AND ICE POLICY - 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 on deck in which passengers may store items to keep them cold. Due to COVID-19, the refrigerator in the cabin area is restricted to use by the captain and crew only. Food, beverage, and ice storage is limited to the on-deck cooler. Please plan accordingly.
  • Most travellers can participate
  • This experience requires good weather. If it’s cancelled due to poor weather, you’ll be offered a different date or a full refund
  • This is a private tour/activity. Only your group will participate
Travel safe during COVID-19
What you can expect during your visit
  • Regularly sanitised high-traffic areas
  • Guides required to regularly wash hands
  • Hand sanitiser available to travellers and staff
What you can expect during your visit
  • Regularly sanitised high-traffic areas
  • Guides required to regularly wash hands
  • Hand sanitiser available to travellers and staff
  • Contactless payment for gratuities and add-ons
  • Face masks required for guides in public areas
  • Gear/equipment sanitised between use
  • Face masks required for travellers in public areas

5.0
6 reviews
Excellent
6
Very good
0
Average
0
Poor
0
Terrible
0

Cherie K
1 contribution
Sunset charter with Captain Mike is an unforgettable experience!
Sep 2021 • Couples
Captain Mike was wonderful! This was our first sailing adventure and it could not have been a better experience. He was so kind and knowledgeable and really made us feel safe. Definitely recommend the later charter time so that you can see sunset over the skyline. We will definitely be doing this again next time I am in town!
Written 7 September 2021
This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.

Ted L
1 contribution
Awesome cruise
Aug 2021
This was a great experience, definitely worth it. We only had two people (romance!) but it would have also been fun as a group thing. Route was awesome, went back and forth from playpen to the Shedd, and you really only get those types of views from a boat offshore. Captain Mike is also a really nice guy, his level of interaction with guests (outside of captaining) is really up to the guests. Would 100% do it again, and next time I'll try and do a Saturday night to see the fireworks.
Written 4 August 2021
This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.

TxRoadWarrior82
Dallas, TX59 contributions
Perfect Experience for Small Corporate Groups
Jul 2021
After over a year without spending time with colleagues due to the pandemic, a private sail on Lake Michigan with Captain Mike was the perfect way to spend an evening catching up. The trip was easy to book on the company's website, Captain Mike was extremely professional and a great host, and the boat was comfortable and relaxing. The pick-up/drop-off location is an easy walk to Millennium Park or a quick Uber/Lyft ride from any downtown area hotel.
Written 23 July 2021
This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.

Lucille S
1 contribution
Sailing into the sunset...
Aug 2018 • Family
Great tour. There were only four of us although the reservations can accommodate 6 people. Captain Mike very nice and gave us a great couple of hours. Highly recommend.
Arizona Visitors
Written 4 August 2018
This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.
Thank you Lucille!
Written 20 August 2018
This response is the subjective opinion of the management representative and not of TripAdvisor LLC.

conciergeben21
Chicago, IL8 contributions
Incredible Sunset Sail!
Aug 2018 • Friends
This was my second experience with Come Sailing and Captain Mike, and it was an even BETTER experience than the first. We went out on a Wednesday evening Sunset Sail and we caught the fireworks display. It was breathtaking to see the city and watch the sunset behind the buildings! Thank you so much for making it such a fun experience, Captain Mike!
Written 4 August 2018
This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.
My pleasure! I'm so glad you had such a great experience. Thank you for sailing with us.
Written 4 August 2018
This response is the subjective opinion of the management representative and not of TripAdvisor LLC.

Peter C
1 contribution
Awesome time sailing!
Jun 2018 • Friends
Had an amazing time sailing with Captain Mike. Great boat and Capt Mike went out of his way to make sure we all had a great time. He definitely knows the best places to see fireworks and/or air and water show.
Written 23 June 2018
This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.
Thanks Peter! Glad you had a great time!
Written 20 August 2018
This response is the subjective opinion of the management representative and not of TripAdvisor LLC.
About the operator

Don’t take it from us – here’s what people have to say about this operator.

By: Come Sailing, Inc.
RavvenaTravel
RavvenaTravel
00
SEE CHICAGO FROM THE WATER IN RELAXATION
We were recommended a sailboat experience on the lake and it was truly exceptional. My brother-in-law and I were in
Sammie P
Sammie P
00
Fantastic!
I cannot reccomend this enough. Magical, relaxing, beautiful and just a blast! Captian Mike was awesome! I would
ChefShawn1983
ChefShawn1983
00
Honeymoon Delight
Captain Mike, Helped make our honeymoon so special. My wife got to take the helm so I think she's now a real life
JenniferJ3542
JenniferJ3542
00
SUPER SAILING
Captain Mike was fantastic! Enjoyed his company , plus he was very knowledgeable abd an expert sailor . We had a
mikemD113NV
mikemD113NV
00
Great sail!
We happened to book the sail on a day that a huge race was in play. It was awesome! Captain Mike was super chill.
Alain7309
Alain7309
00
Great time on the lake
Thank you Mike for the nice ride on your beautiful boat. We had such a great time and fun ! Appreciate that we cou
Grantmillie
Grantmillie
00
No better way to see Chicago!
Come Sailing and Captain Mike are absolutely the best in Chicago. The skyline that has no equal can only be best e
Bobby G
Bobby G
00
Best way to sightsee in Chicago, in private!
Sailing on beautiful Lake Michigan offers an experience not to be missed! ‘Come Sailing Chicago’ offers a Catalina
Kim V
Kim V
00
Go Sailing
Great tour! Fun experience. Excellent city views. Captain Mike was awesome. We lucked out and scored amazing weathe
SChantalMD
SChantalMD
00
Front Row "Seats" for the Fireworks
I don't know where to begin in writing this review because every part of the evening was purely magical! First of a
Colin M
Colin M
00
Truly brilliant and unforgettable trip
This is the #1 must do thing in Chicago. In relative terms it represents fantastic value. Captain Mike was fabulous
jurban333
jurban333
00
The Perfect Sail
Can't say enough good things about this experience, from start to finish it was A+++. The booking process, the boat
A1355CImichaelo
A1355CImichaelo
00
Go Sailing!
We were initially attracted by the colorful flag flying off the back of the boat. After meeting Captain Mike we kne
conciergeben21
conciergeben21
00
WHAT A WAY TO SPEND THE DAY!!!
What an amazing trip out on Lake Michigan! Captain Mike was such a great host and guide. Such incredible views of
Marisela H
Marisela H
00
Sunset sail
Had a great time, amazing service I recommend them to anyone who wants too see the Chicago skyline from the water �
Frequently Asked Questions about Private Sunset Sail on Lake Michigan with Breathtaking Views of Chicago


Private Sunset Sail on Lake Michigan with Breathtaking Views of Chicago price starts from £309.58. Discover and book Private Sunset Sail on Lake Michigan with Breathtaking Views of Chicago on Tripadvisor

Private Sunset Sail on Lake Michigan with Breathtaking Views of Chicago cancellation policy: For a full refund, cancel at least 24 hours in advance of the start date of the experience. Discover and book Private Sunset Sail on Lake Michigan with Breathtaking Views of Chicago on Tripadvisor

Private Sunset Sail on Lake Michigan with Breathtaking Views of Chicago is hosted by Come Sailing, Inc.. Read reviews, discover additonal experiences or contact Come Sailing, Inc. on Tripadvisor. Discover and book Private Sunset Sail on Lake Michigan with Breathtaking Views of Chicago on Tripadvisor