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    Find Sailing Charters Near You

    4.9
    (4,261 Reviews)

    Page 1 of 10 • 240 listings

    32ft Sailboat for Beautiful Sail on Lake Erie (Cleveland area)
    Sailing in Cleveland · 6 guests

    32ft Sailboat for Beautiful Sail on Lake Erie (Cleveland area)

    New
    $200-$325hour
    Four Winns Cruiser for Charter in Michigan City
    Sailing in Michigan City · 5 guests

    Four Winns Cruiser for Charter in Michigan City

    New
    $150hour
    38' Catalina Sailing Cruise in Chicago
    Sailing in Chicago · 6 guests

    38' Catalina Sailing Cruise in Chicago

    5.0
    $250hour
    Charter this Beautiful Catalina 36 Sailboat w/Captain in Chicago, Illinois
    Sailing in Chicago · 6 guests

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

    5.0
    $225hour
    Charter this Classic Shannon Sailboat w/ Professional Captain in Chicago
    Sailing in Chicago · 4 guests

    Charter this Classic Shannon Sailboat w/ Professional Captain in Chicago

    5.0
    $202hour
    40' Sailboat Monroe Harbor Chicago
    Sailing in Chicago · 6 guests

    40' Sailboat Monroe Harbor Chicago

    New
    $400hour
    Set Sail with 36' Sailing Boat in Downtown, Chicago
    Sailing in Chicago · 6 guests

    Set Sail with 36' Sailing Boat in Downtown, Chicago

    5.0
    Superowner
    $225hour
    Beautiful Ranger 22 Sailboat for rent in Chicago Monroe Harbor
    Sailing in Chicago · 3 guests

    Beautiful Ranger 22 Sailboat for rent in Chicago Monroe Harbor

    4.8
    $115-$120hour
    37' Luxury Sailboat with Captain in Chicago, Illinois
    Sailing in Chicago · 10 guests

    37' Luxury Sailboat with Captain in Chicago, Illinois

    5.0
    Superowner
    $299hour
    Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois
    Sailing in Chicago · 6 guests

    Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois

    5.0
    Superowner
    Best of 2023
    $220hour
    Charter a 31' Pearson Cruising Sloop, Chicago
    Sailing in Chicago · 6 guests

    Charter a 31' Pearson Cruising Sloop, Chicago

    4.5
    Superowner
    $200hour
    38' Sailing Catamaran, Chicago's Largest!
    Sailing in Chicago · 12 guests

    38' Sailing Catamaran, Chicago's Largest!

    5.0
    Superowner
    $440-$500hour
    Private Cruise onboard Hunter Legend Sailboat in Chicago
    Sailing in Chicago · 6 guests

    Private Cruise onboard Hunter Legend Sailboat in Chicago

    5.0
    Superowner
    $200hour
    41' Morgan Classic Sloop in Muskegon, Michigan!!! Min $135 pp 2 persons
    Sailing in Muskegon · 6 guests

    41' Morgan Classic Sloop in Muskegon, Michigan!!! Min $135 pp 2 persons

    5.0
    $89person
    Hunter 43 Sailing Yacht in Oakville, Ontario
    Sailing in Oakville · 5 guests

    Hunter 43 Sailing Yacht in Oakville, Ontario

    5.0
    $271hour
    41ft Sailing Crusing Monohull Charter on ''White Lake'' Michigan, USA.
    Sailing in Whitehall · 6 guests

    41ft Sailing Crusing Monohull Charter on ''White Lake'' Michigan, USA.

    5.0
    $115hour
    K25 Racing Boat Clarisse
    Sailing in Mississauga · 5 guests

    K25 Racing Boat Clarisse

    5.0
    Snoozed - Active 06 May 2024
    35ft C&C 35 Sailboat in Toronto
    Sailing in Etobicoke · 6 guests

    35ft C&C 35 Sailboat in Toronto

    5.0
    $181hour
    Sail Lake Michigan Racine, WI
    Sailing in Racine · 6 guests

    Sail Lake Michigan Racine, WI

    5.0
    $220hour
    27 Foot Sailboat for a Day of Fun in the Sun in Toronto
    Sailing in Toronto · 6 guests

    27 Foot Sailboat for a Day of Fun in the Sun in Toronto

    5.0
    $54person
    Sailing Charter in Toronto
    Sailing in Toronto · 6 guests

    Sailing Charter in Toronto

    5.0
    $72person
    28' Sailboat for 5 guests in Toronto
    Sailing in Toronto · 5 guests

    28' Sailboat for 5 guests in Toronto

    New
    $235hour
    41' Beneteau Oceanis Sailing Yacht in Toronto for 12 Guests
    Sailing in Toronto · 12 guests

    41' Beneteau Oceanis Sailing Yacht in Toronto for 12 Guests

    New
    $435hour
    38' Sailing Yacht in Toronto, Ontario
    Sailing in Toronto · 8 guests

    38' Sailing Yacht in Toronto, Ontario

    New
    $400hour

    Local Sailing Reviews

    1. BK

      Benjamin

      Set Sail with 36' Sailing Boat in Downtown, Chicago

      Ray gives the ultimate trip, perfectly followed our vibe. The boat was beautiful. It was perfect! Can't recommend highly enough!

    2. KH

      Katie

      Charter this Classic Shannon Sailboat w/ Professional Captain in Chicago

      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!

    3. RJ

      Robert

      Set Sail with 36' Sailing Boat in Downtown, Chicago

      Ray and Cassidy were great! We didn't have a planned route or destination so Ray chose his own and it was incredible! The views were amazing and we had the best seats in the house to the Air and Water show! Ray and Cassidy were both friendly and knowledgeable through the whole experience. We couldn't have asked for a better crew! The boat was beautiful and a couple of us even had a chance to steer it. All around amazing.

    4. BG

      Bradley

      Set Sail with 36' Sailing Boat in Downtown, Chicago

      Ray and Cassidy were very friendly, and allowed us to help sail the vessel as we requested. Ray is very qualified and enjoys sailing. I'm sure we could have laid back and relaxed as they did all of the work, but I think our experience was much better for having been more involved. Thanks, and we'll definitely use Ray again if we are back in the area and have the chance!

    5. Beth

      Beth

      Set Sail with 36' Sailing Boat in Downtown, Chicago

      I can’t say enough for how great my experience was with Captain Ray, Captain Dawn and Captain Ted. From the initial booking all the way through the actual sailing, they were responsive, accommodating and amazing to work with. My fiancé and I did our engagement photos aboard Siren Song and the experience and photos exceeded everything I dreamed this day and these photos could be. Highly recommend!

    6. LG

      Leigh

      Set Sail with 36' Sailing Boat in Downtown, Chicago

      Ray and Dawn were excellent, professional captains. We departed around 6pm and took a lovely sunset trip around the harbor. Unfortunately the winds were a bit too high to sail further out onto the lake, but we all appreciated the safe and relaxing trip. Highly recommend!

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