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Charter this Classic Shannon Sailboat w/ Professional Captain in ChicagoCharter this Classic Shannon Sailboat w/ Professional Captain in ChicagoCharter this Classic Shannon Sailboat w/ Professional Captain in ChicagoCharter this Classic Shannon Sailboat w/ Professional Captain in Chicago

Charter this Classic Shannon Sailboat w/ Professional Captain in Chicago

5.0(9 reviews)
10 bookings

Enjoy a private sailing experience for up to six people along Chicago’s beautiful lakefront.  Kick back, relax, and let our 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 the guest list to music selection to sailing route. All charters are NON-SMOKING experiences. Druid, a 1981 Shannon 28, is a classic heavy displacement, blue water cruiser with a cutter rig. She was designed and built to handle any weather condition or sea state. The Shannon Sailboat Company is world-renowned for the quality and beauty of their sailboats and Druid is no exception. Her bright work and interior are warm and inviting. With an icebox for keeping food and beverages cold and speakers in the cockpit for enjoying your favorite music, Druid is equipped to cater to your needs. Druid is in the only Shannon sailboat available for charter on Lake Michigan as far as we are aware. Rates: • Two-hour Weekend Charter (Friday thru Sunday): $454 • Two-hour Weekday Charter (Monday thru Thursday): $403 PLEASE READ ALL OF THE TERMS AND CONDITIONS BEFORE BOOKING! If you have any questions, we can answer those through GetMyBoat’s messaging platform before you pay. Just hit, “Request to Book” and send us an inquiry for a custom offer.

Starting from

  • Hourly
    4 hrs max
  • $202/hr
    2 hrs min


51 total bookings
Captain Provided in Price
Professional Captain provided and included in the price.
4 guests
Cruising Monohull

Check Availability


5.0 (9 reviews)
  • Listing Accuracy

  • Departure & Return

  • Vessel & Equipment

  • Communication

  • Value

  • Itinerary & Experience

  1. Charter this Classic Shannon Sailboat w/ Professional Captain in Chicago
  2. Charter this Classic Shannon Sailboat w/ Professional Captain in Chicago
2 photos have been added by reviewers who booked this listing.
  1. KH

    Michael was incredible!!! He was so friendly and made our experience so comfortable, relaxing, and fun! I wish he was the captain of every boat I go on moving forward because he was such a wonderful person to have around! Thank you so much Michael! We appreciate your help!

  2. AG

    We never got to sail because of weather but mike was outstanding about scheduling, refunds and flexibility. I definitely plan to book with him again next season.

  3. CN

    Great experience with Captain Mike! Communicated the plan super well and has such a fun time sailing. Views of the city were amazing, no complaints here!

  4. GT

    We had a great time with Mike. Highly recommended.

  5. KC


51 total bookings

Captain Mike is a US Coast Guard licensed Charter Captain. He grew up sailing the waters of Lake Michigan with his Dad, who taught him how to sail from an early age. After many summers spent sailing in Door Country, Wisconsin and Traverse City, Michigan, Captain Mike purchased a sailboat of his own, a 36-foot Catalina that he named Bernard. In addition to sharing his love of sailing with other people, Captain Mike has developed a passion for sailing solo. He has competed in three long distance (100 miles plus) solo sailing races (including two races from Chicago, Illinois to Mackinac Island, Michigan) and has achieved membership in the Great Lakes Single-Handed Society. Not only do these extended solo sailing voyages allow Captain Mike to practice and improve his sailing skills, they also provide opportunities to see beautiful sunrises sunsets, and amazing night skies from the unique viewpoint of the water, away from the bright lights of the city and often without any land in sight. Whenever possible, Captain Mike loves to have his wife and three daughters join him for sailing adventures throughout the Great Lakes

Features & Details

Shannon 28
  • Bluetooth
  • Fuel type: Diesel
  • Single Engine
  • Head
  • Cabin

Approximate Location

You’ll get directions to the departure location when you make a booking.

The boat's approximate location on a map

Cancellation Policy

Full refund up to 2 days prior.

Additional Terms & Information

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. 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. SWIMMING Swimming is not permitted from this boat. 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. 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. ANIMALS ARE PROHIBITED Unfortunately, we cannot accommodate animals of any type. 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. 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 or adjustment to price. 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. MINIMUM AGE Passengers must be at least 10 years old. 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. SOCIAL DISTANCING 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. 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. OUR COMMITMENT TO A CLEAN AND SAFE SAILING ENVIRONMENT Sailboats are washed with biodegradable boat soap each morning prior to charters. 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. 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.

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