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    Find Sailing Charters Near You

    4.9
    (4,949 Reviews)

    Page 1 of 10 • 240 listings

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

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

    5.0
    $325+/hour
    20ft Bayliner VR5 Boat in Rockville, IN
    Powerboats in Indiana · 6 guests

    20ft Bayliner VR5 Boat in Rockville, IN

    5.0
    $510/day
    2hr Sunset Sail from the port of South Haven Mi. on a Catalina 36
    Sailing in South Haven · 6 guests

    2hr Sunset Sail from the port of South Haven Mi. on a Catalina 36

    5.0
    $200/hour
    2hr Day Sail from the port of South Haven Mi. on a Catalina 36
    Sailing in South Haven · 6 guests

    2hr Day Sail from the port of South Haven Mi. on a Catalina 36

    5.0
    $175/hour
    Sail Lake Macatawa and cruise past the lighthouse, Big Red onto Lake Michigan
    Sailing in Holland · 6 guests

    Sail Lake Macatawa and cruise past the lighthouse, Big Red onto Lake Michigan

    New
    $150/hour
    1986 22ft Catalina Sailboat in Holland, Michigan
    Sailing in Holland · 6 guests

    1986 22ft Catalina Sailboat in Holland, Michigan

    New
    $75+/hour
    Limited Availability
    Lets go sailing on a world class 40ft Pacific Seacraft Sailboat from Chicago
    Sailing in Chicago · 6 guests

    Lets go sailing on a world class 40ft Pacific Seacraft Sailboat from Chicago

    New
    $230+/hour
    Private 38' Catalina Sailing Catamaran Charter for up to 7 Person with Captain
    Sailing in Chicago · 6 guests

    Private 38' Catalina Sailing Catamaran Charter for up to 7 Person with Captain

    5.0
    $450/hour
    13 person Sailing Yacht Chicago Weekday Special 4th Hour Free!
    Sailing in Chicago · 13 guests

    13 person Sailing Yacht Chicago Weekday Special 4th Hour Free!

    5.0
    $550/hour
    Private Jeanneau Sun Odyssey 37ft Sailboat Chicago Cruise with 10 Guests
    Sailing in Chicago · 10 guests

    Private Jeanneau Sun Odyssey 37ft Sailboat Chicago Cruise with 10 Guests

    5.0
    Superowner
    $250/hour
    Instant Book
    Set Sail with 36' Sailing Boat in Downtown, Chicago for 6 Guests
    Sailing in Chicago · 6 guests

    Set Sail with 36' Sailing Boat in Downtown, Chicago for 6 Guests

    5.0
    $225/hour
    Come Sailing at Navy Pier Marina, Chicago - Beautiful 36' Catalina Sailboat
    Sailing in Chicago · 6 guests

    Come Sailing at Navy Pier Marina, Chicago - Beautiful 36' Catalina Sailboat

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

    Beautiful Ranger 22 Sailboat for rent in Chicago's Monroe Harbor

    4.9
    Snoozed - Active 15 Jul 2026
    Sailing Lessons with Chicago's #1 Rated Sailing School
    Tours in Chicago · 6 guests

    Sailing Lessons with Chicago's #1 Rated Sailing School

    5.0
    $175+/hour
    38ft Lagoon Catamaran Sailing Lessons in Chicago
    Tours in Chicago · 6 guests

    38ft Lagoon Catamaran Sailing Lessons in Chicago

    New
    $350+/hour
    Limited Availability
    Charter a 31' Pearson Cruising Sloop, Chicago
    Sailing in Chicago · 6 guests

    Charter a 31' Pearson Cruising Sloop, Chicago

    4.5
    $200+/hour
    Limited Availability
    Private Cruise Onboard 32ft Hunter Legend Sailboat in Chicago
    Sailing in Chicago · 6 guests

    Private Cruise Onboard 32ft Hunter Legend Sailboat in Chicago

    5.0
    $200/hour
    Chicago's Largest Chartered 38ft Lagoon Sailing Catamaran
    Sailing in Chicago · 13 guests

    Chicago's Largest Chartered 38ft Lagoon Sailing Catamaran

    5.0
    $440/hour
    Limited Availability
    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 2026
    $220/hour
    Captained Charter 62' Azimut Luxury Motor Yacht Rental in Chicago!
    Events in Chicago · 13 guests

    Captained Charter 62' Azimut Luxury Motor Yacht Rental in Chicago!

    5.0
    $1,190/hour
    Limited Availability
    No tie-ups: 39' Catalina Sailboat with Huge Cockpit in Chicago
    Sailing in Chicago · 12 guests

    No tie-ups: 39' Catalina Sailboat with Huge Cockpit in Chicago

    4.8
    $245/hour
    Instant Book
    Private Cruise on 40’ Luxury Sailing Yacht - Beneteau Oceanis 393 “Vagabond”
    Sailing in Chicago · 10 guests

    Private Cruise on 40’ Luxury Sailing Yacht - Beneteau Oceanis 393 “Vagabond”

    New
    $275/hour
    41' Morgan Classic Sloop in Muskegon, Michigan!!!
    Sailing in Muskegon · 6 guests

    41' Morgan Classic Sloop in Muskegon, Michigan!!!

    5.0
    $100/hour
    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
    $140/hour

    Top Destinations Nearby

    Local Sailing Reviews

    1. WK

      William

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

      Nijole was a wonderful captain with great communication and flexibility. The change in plans due to weather was seamless. We had a great time on the lake with Nijole, Remus and Piper and will chose her again if we are back in Chicago and want to go out for a sail. Thanks again Nijole!

    2. AA

      ADOLFO

      Captained Charter 62' Azimut Luxury Motor Yacht Rental in Chicago!

      This was an amazing boat! It’s HUGE!! Captain Lester was a true professional who catered to all are requests. This was the best day of our summer. I would highly recommend this boat! Truly great!

    3. Aisat

      Aisat

      13 person Sailing Yacht Chicago Weekday Special 4th Hour Free!

      Captain Russell & his team were so nice and helpful and accommodating and the vessel was perfect for a group of 10-12. We had the right vibes and experience and would highly recommend!

    4. Eric

      Eric

      Sailing Lessons with Chicago's #1 Rated Sailing School

      I had a four hour private lesson with Doug and small crew. All were very helpful and knowledgeable, it was a great learning experience. I look forward to joining them again.

    5. Erica

      Erica

      Beautiful Ranger 22 Sailboat for rent in Chicago's Monroe Harbor

      Ben is wonderful he is so passionate and knowledgeable about sailing and he made it a great time.

    6. JD

      Jorge

      No tie-ups: 39' Catalina Sailboat with Huge Cockpit in Chicago

      Captain Dennis and Kate were great hosts. Everything was perfect

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