Private Sunset Sails

Private Sunset Sails

Detail Duration: 2 hours
Sunset Sail in Chicago

The Private Sunset Sail is a two-hour boat tour. It is a private charter. There is a customized sailing experience. You can have a relaxing sail along the Chicago beautiful lakefront. It is for the visitors and a couple of friends or maybe your family.

The tour is only for you and a guest or maybe family. Captain Mike and the crew members make sure you have a safe and fun tour. Please come and see Captain Mike and sail with the best. The boat has a refrigerator and ice for the guest.

Do not bring glass containers on the trip. You can bring sunglasses, sunscreen, and a Bluetooth device to download music. There are about six passengers on the tour. You can enjoy a relaxing and a see the view of Chicago. A bag of ice and local taxes are included on the tour.

The tour does not include food and drinks or hotel pick up and drop offs. Your confirmation number will need to be present when coming on the trip. There is no smoking, no glass, and customer behavior should be appropriate. There can be food or drinks on the deck.

The tour rules are there should be no guns, knives, or weapons allowed on the boat. If a visitor wants to swim they would have to sign a waiver. A person gets sick then they should remain on the deck. You can take the tour with your family or maybe a couple of friends. A private sail is a relaxing and comfortable tour. The lakefront view in Chicago is so beautiful. You can have great drink and food on the boat tour with great crew members who can make sure the visitors are safe.

The Experience

Come Sailing is Chicago's Premier Private Sailing Charter offering daily sailing charters, sunset sails, fireworks cruises, and customized sailing experiences.

During this two-hour private charter our experienced crew will treat you to a relaxing sail along Chicago's beautiful lakefront. Exclusively for you and your invited guests, no other passengers will be aboard. Feeling adventurous? Take a turn at the helm. Captain Mike and his crew will be there to ensure a safe and fun experience. Whatever your choice, these exclusive sailing charters are tailored to your preferences. Captain Mike's mission is to provide safe, enjoyable, customized sailing adventures for his customers. Come Sailing with Captain Mike. 

There's a refrigerator on board that you may use and a bag of ice will be supplied. Please avoid bringing glass containers if possible. Bring your camera, your sunglasses, some sunscreen, and don't forget to bring a Bluetooth device loaded with your favorite music. 

  • Private Sailing Charter, only you the your invited guests
  • Up to six passengers
  • Enjoy a relaxing sail along Chicago's beautiful lakefront
  • Captain Mike and his crew will be there to ensure a safe and fun experience
  • Captain services included with all charters
  • BYOB but please avoid bringing glass containers

See you on the water.

Pickup & Return:
Monroe Harbor Charter Wall.
Departure Times: 6:40 PM


  • Private sailing charter for up to six passengers
  • Captain services
  • 1 bag of ice
  • Local taxes

Does not include:

  • Food and drinks
  • Gratuities (optional)
  • Hotel pickup and drop-off

Additional Information:

  • Confirmation will be received at time of booking

    All charter 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.


    Customers and guests are allowed to bring and consume reasonable amounts of alcoholic beverages within the bounds of Illinois State law.


    Glass containers are prohibited.  Please do not bring them.


    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. 


    No guns, knives, or weapons of any kind are 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.


    Any person wishing to swim during the charter will be required to sign a waiver and release upon boarding the sailboat.  Swimming will be allowed on the morning and day sail charters only and will be at the captain's discretion.


    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.


    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. 


    Cleaning fees will be equivalent to the standard, full price of your 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.


    Gift Certificates may not be redeemed for cash.  Gift certificates may be used to purchase products and services offered by Come Sailing, Inc.  Gift certificate will expire one year from the date of purchase.  


    The late arrival of customers and guests may result in a shortened charter sail without refund or adjustment to price.


    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 and to use your name, 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 such minor child.

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