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Beautiful sunset sailing with Chicago on the bow!
Mesmerizing sunsets silhouette the Chicago skyline
Capturing the city lights at dusk. The best place to view the city at night is on our sailboat.
Taking a break and relaxing on the bow for a beautiful sunset.
At dusk after the sun has set the city lights begin their show.

Chicago Private Sunset Sail on Lake Michigan

By Come Sailing, Inc.
10 out of 10
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Features
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Overview

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.

Activity location

  • Come Sailing, Inc.
    • 400 East Monroe Street
    • 60603, Chicago, Illinois, United States

Meeting/Redemption Point

  • East Monroe Street & South Lake Shore Drive
    • 60601, Chicago, Illinois, United States

Check availability

Sorry this activity isn't available on Sat, 16 Nov
Please choose a different date

What's included, what's not

  • What's includedWhat's includedUse of Bluetooth speakers
  • What's includedWhat's includedProfessional captain licensed by the US Coast Guard
  • What's includedWhat's includedAll applicable taxes
  • What's excludedWhat's excludedService charge
  • What's excludedWhat's excludedFood and drinks (you may bring your own)
  • What's excludedWhat's excludedParking

Know before you book

  • Public transport 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, vapour 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 drinks 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 behaviour will not be tolerated. Any behaviour 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 drinks may be consumed on deck. Please clean up any spilled food or drink and take your rubbish 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 rubbish 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.
  • 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 MASKS ARE OPTIONAL - 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 POLICY - 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 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 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 minimise 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 bathroom on board each boat. However, the bathrooms 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 bathroom. We strongly encourage you to use the public bathrooms 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 drinks 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, drink, 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.
  • In accordance with EU regulations about consumer rights, activities services are not subject to the right of withdrawal. Supplier cancellation policy will apply.

Activity itinerary

Come Sailing, Inc.
  • 2h
  • Admission ticket included
We’ll depart from the north side of Monroe Harbour at our dedicated pick-up/drop-off spot. 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 wind the 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.
Buckingham Fountain (Pass by)
Our charter begins with a quick motor passed a part of Monroe Harbour named in honour of a visit by Queen Elizabeth II. On July 6, 1959, a small barge ferried Her Majesty from HMY Britannia anchored outside of Monroe Harbour 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 centrepiece 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 honour of her brother Clearance Buckingham.
Shedd Aquarium (Pass by)
Another building which cannot be ignored as we depart from Monroe Harbour is the Shedd Aquarium which sits prominently at the south end of Monroe Harbour. Completed in 1930, the Shedd Aquarium’s mission is “Sparking compassion, curiosity and conservation for the aquatic animal world”. The large dark windows facing the lake house the Abbott Oceanarium exhibit. Added in 1991, the Oceanarium features Pacific white-sided dolphins and beluga whales.
Adler Planetarium (Pass by)
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. As we head out into the Lake, we get to see a side of this marvellous 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.
Soldier Field (Pass by)
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.
Navy Pier (Pass by)
One of the most recognised 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!
Chicago Skyline (Pass by)
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.

Location

Activity location

  • LOB_ACTIVITIESLOB_ACTIVITIESCome Sailing, Inc.
    • 400 East Monroe Street
    • 60603, Chicago, Illinois, United States

Meeting/Redemption Point

  • PEOPLEPEOPLEEast Monroe Street & South Lake Shore Drive
    • 60601, Chicago, Illinois, United States

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