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    s/v Bernard: 2004 Catalina 36 mkII.  Photo taken while anchored in Pigeon Lake, MI.
    s/v Bernard under sail with Capt. Mike at the helm.
    Roomy cockpit.
    Roomy cockpit.

    Charter this Beautiful Catalina 36 Sailboat w/Professional in Chicago, Illinois

    18 reviews
    43 bookings
    2 hours minimum

    Take a break, Come Sailing, and enjoy some summer fun in the sun in Chicago, Illinois! Charter the "Bernard" Catalina 36 Sailing Yacht for up to 6 person. Rate as low as $199 per hour and a minimum booking of 2 hours. Rates: • Weekend (Friday thru Sunday): $452 • Weekdays (Monday thru Thursday): $398 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 guest list to music selection to sailing route.  All charters are NON-SMOKING experiences. Bernard, a Catalina 36 built in 2004, is a classic cruising design perfect for sailing on the Great Lakes. Configured for singlehanded sailing, she has competed in many long distance solo races; the latest of which was the 2015 Solo Mac. (Ask Captain Mike about the Pickle Flag!) The largest sailboat in our fleet, Bernard has plenty of room for a group of six to spread out and relax. She features a comfortable cabin for relaxing out of the sun, a large forward deck perfect for sunbathing or watching fireworks, and a roomy cockpit (Check out the Rock Star seats!). With a refrigerator for keeping food and beverages cold and speakers in the cockpit for enjoying your favorite music, Bernard is equipped to cater to your needs. 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.

    Captain is included.
    A captain is provided by the listing owner to host and operate the trip.
    6 guests
    Cruising Monohull


    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

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    18 reviews

    4.9 out of 5!

    • Listing Accuracy

    • Departure & Return

    • Vessel & Equipment

    • Communication

    • Value

    • Itinerary & Experience

    1. Charter this Beautiful Catalina 36 Sailboat w/Professional in Chicago, Illinois
    2. Charter this Beautiful Catalina 36 Sailboat w/Professional in Chicago, Illinois
    3. Charter this Beautiful Catalina 36 Sailboat w/Professional in Chicago, Illinois
    4. Charter this Beautiful Catalina 36 Sailboat w/Professional in Chicago, Illinois
    5. Charter this Beautiful Catalina 36 Sailboat w/Professional in Chicago, Illinois
    6. Charter this Beautiful Catalina 36 Sailboat w/Professional in Chicago, Illinois
    7. Charter this Beautiful Catalina 36 Sailboat w/Professional in Chicago, Illinois
    7 photos have been added by reviewers who booked this listing.
    1. ML

      Wonderful sailing experience! Captain Mike was very helpful and professional during the whole trip. My friends and I have already decided that we will try this again next summer!

    2. BF

      Great time!

    3. SA

      Trip was very smooth. Captain Mike was very accommodating. If it is your first time sailing, this is the trip that you should take.

    4. AH

      Captain Mike did a great job making our trip fun and memorable! Highly recommend

    5. MM

      Terrific captain! Well organized, safe, clean - he shared wonderful stories during our charter and made sure we all had a wonderful afternoon. We give him our highest recommendation!

    Features & Details

    • Galley Stove & Oven
    • Bluetooth
    • Life jackets/required safety gear
    • Cabin
    • Wheel steering
    • Bimini
    • Inboard Engine
    • Autopilot
    • CD Player
    • Chart Plotter
    • Dodger
    • Single Engine
    • Fuel type: Diesel
    • Furling Headsail
    • Furling Mainsail

    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

    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 - 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. 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 may be permitted on charters of 3 hours or longer. Swimming is not guaranteed and is at the captain's discretion. If swimming is deemed permissible by the captain, every passenger on board will be required to sign a waiver & release prior to swimming. Swimming will not be allowed after the departure time of our Sunset Sail schedule for that same day. SWIMMING IS AT YOUR OWN RISK! 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 our company is your implied consent to be filmed, photographed, and recorded. Furthermore, by boarding any of our sailboats you are granting our company, 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 our company. 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.

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