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Private Sunset Sail on Lake Michigan with Breathtaking Views of Chicago

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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.

Customer Reviews

Relevant Reviews
Jovan M
July 29, 2021
Mike was awesome! It was my first time on a private sail with friends. We were comfortable, the sail was smooth and we had a great time. We didn’t want it to end.
June 8, 2021
Captain Mike was awesome! So much fun and very knowledgeable. We had our own playlist playing the whole time and the views..... the best I’ve ever seen. We sipped wine and had the time of our lives. It was worth every penny.
7 days ago
The captain was ready for us when we arrived. He was very informative. Great experience from beginning to end!

About This Deal

This is a typical itinerary for this product

Stop At: Come Sailing, Inc., Monroe Harbor, Chicago, IL 60603, USA

We’ll depart from the north side of Monroe Harbor 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 the day, 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 sail on Lake Michigan during which you will sail in close proximity to some or all of the landmarks listed in the itinerary below.

Duration: 2 hours

Pass By: Buckingham Fountain, Grant Park, Chicago, IL 60605

Our charter begins with a quick motor passed a part of Monroe Harbor named in honor of a visit by Queen Elizabeth II. On July 6, 1959, a small barge ferried Her Majesty from 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; however, Buckingham fountain has nothing to do with 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, himself a patron of the arts and fellow philanthropist.

Pass By: Shedd Aquarium, 1200 S. Lake Shore Drive, Chicago, IL 60605-2490

Another building which cannot be ignored as we depart from Monroe Harbor is the Shedd Aquarium which sits prominently at the south end of Monroe Harbor. 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.

Pass By: Adler Planetarium, 1300 S Lake Shore Dr, Chicago, IL 60605-2489

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 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: Soldier Field, 1410 S Museum Campus Dr, Chicago, IL 60605-2902

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: Navy Pier, 600 E Grand Ave, Chicago, IL 60611-3419

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: Chicago Skyline, Chicago, IL 60601

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.

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 travelers can participate
  • This experience requires good weather. If it’s canceled 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
  • Face masks required for travelers in public areas
  • Face masks required for guides in public areas
  • Hand sanitizer available to travelers and staff
  • Regularly sanitized high-traffic areas
  • Gear/equipment sanitized between use
  • Guides required to regularly wash hands
  • Contactless payments for gratuities and add-ons
  • Professional US Coast Guard licensed captain
  • Use of Bluetooth speakers
  • All applicable taxes
  • Entry/Admission - Come Sailing, Inc.

  • Gratuities
  • Food and Drinks
  • Parking

2 hours

Return Details
Returns to original departure point

Voucher Info
You can present either a paper or an electronic voucher for this activity.

The tour identified in this promotion is made available through Viator. Groupon is not affiliated with or sponsored by the Come Sailing, Inc. in connection with this deal. Please contact Groupon customer service for all inquiries related to this offer. Inquiries placed to Viator will be directed back to Groupon.

This offer is not eligible for promo codes.

Fine Print

  • Voucher valid only for date and time listed; may not be exchanged or redeemed for other dates.
  • Purchaser name and phone number must be provided at checkout; this information will be shared with Viator and the tour operator for purposes of order fulfillment.
  • Groupon promo codes may not be used for this offer. Groupon voucher Terms of Sale and Extraordinary Event Policy do not apply.
  • See Viator voucher terms under "Viator Vouchers" here.
  • Merchant is solely responsible to purchasers for the care and quality of the advertised goods and services. Offer is not eligible for our promo codes or other discounts.