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The Best Sailboat Rentals in Connecticut

Browse, book, and get out onto the water with local captains and boat owners.

    Our Favorite Sailboat Rentals in Connecticut

    5 (163 reviews)

    •

    • Hunter Marine Passage 450 - Sail from Norwalk/Westport, CT
      Sailing in Norwalk · 12 guests

      Hunter Marine Passage 450 - Sail from Norwalk/Westport, CT

      4.7
      Superowner
      $200/hour
    • 41' Beautiful sailing catamaran, perfect for lounging, swimming, and sailing
      Sailing in Sag Harbor · 12 guests

      41' Beautiful sailing catamaran, perfect for lounging, swimming, and sailing

      5.0
      $750+/hour
    • Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut
      Tours in Stamford · 6 guests

      Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut

      4.9
      Superowner
      $225+/hour
    • 42' Catalina Sailing Yacht in the Hamptons - For a perfect day on the water /)
      Sailing in Sag Harbor · 6 guests

      42' Catalina Sailing Yacht in the Hamptons - For a perfect day on the water /)

      5.0
      $312+/hour
    • Enjoy the Hamptons waters on wonderful and unique Classic 45' Mahogany Trimaran
      Sailing in Sag Harbor · 25 guests

      Enjoy the Hamptons waters on wonderful and unique Classic 45' Mahogany Trimaran

      5.0
      $900+/hour
    • 36ft Beneteau Private Sailing Charter – Explore Mystic and Fisher's Island
      Sailing in Stonington · 6 guests

      36ft Beneteau Private Sailing Charter – Explore Mystic and Fisher's Island

      5.0
      $250+/hour
    • Cruise Long Island Sound Aboard 62ft Lagoon 620 Catamaran in Greenwich, CT
      Sailing in Greenwich · 12 guests

      Cruise Long Island Sound Aboard 62ft Lagoon 620 Catamaran in Greenwich, CT

      5.0
      $1,500/hour
    • Classic Beauty: Nautor Swan 46' Bluewater Cruiser, Sag Harbor, New York
      Sailing in Sag Harbor · 6 guests

      Classic Beauty: Nautor Swan 46' Bluewater Cruiser, Sag Harbor, New York

      5.0
      $310+/hour
    • Charter 36ft Sloop In Westbrook, Connecticut
      Sailing in Westbrook · 6 guests

      Charter 36ft Sloop In Westbrook, Connecticut

      5.0
      $250/hour
    • Sag Harbor 73ft Luxuriously Custom Schooner Private Sailing Experience
      Sailing in Sag Harbor · 41 guests

      Sag Harbor 73ft Luxuriously Custom Schooner Private Sailing Experience

      5.0
      $1,100+/hour
    • Learn To Sail 23' Pearson With Instructor In Sag Harbor, New York
      Sailing in Sag Harbor · 6 guests

      Learn To Sail 23' Pearson With Instructor In Sag Harbor, New York

      New
      $249/hour
    • Private Sailing Charter – Explore the Hamptons from Sag Harbor Aboard a Beneteau
      Sailing in Sag Harbor · 6 guests

      Private Sailing Charter – Explore the Hamptons from Sag Harbor Aboard a Beneteau

      New
      $230+/hour
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    Suggested Searches

    This weekend$100-$300 trips2-4 peopleCaptained

    Types of Boats Popular in Connecticut

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    Most Popular Yacht Rentals in Connecticut

    • 84ft Azimut – Luxury Yacht + Jet Skis, Seabobs & Jacuzzi
      Events in Greenport · 12 guests

      84ft Azimut – Luxury Yacht + Jet Skis, Seabobs & Jacuzzi

      5.0
      Superowner
      Best of 2026
      $950/hour
    • Charter a 30' Classic Wooden Motor Boat in East Hampton, NY
      Events in East Hampton · 6 guests

      Charter a 30' Classic Wooden Motor Boat in East Hampton, NY

      5.0
      $388+/hour
    • 36' 2023 Aquila Catamaran + Seabob Yacht Rental in East Hampton, New York
      Powerboats in East Hampton · 12 guests

      36' 2023 Aquila Catamaran + Seabob Yacht Rental in East Hampton, New York

      New
      $1,247/hour
    • 36' 2025 De Antonio + Seabob Yacht Rental in Sag Harbor, New York
      Events in Sag Harbor · 12 guests

      36' 2025 De Antonio + Seabob Yacht Rental in Sag Harbor, New York

      New
      $1,063/hour
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    Most Popular Boat Tours in Connecticut

    • A large and luxurious French Beneteau Farr 57 Sailing Yacht for up to 6
      Sailing in Sag Harbor · 6 guests

      A large and luxurious French Beneteau Farr 57 Sailing Yacht for up to 6

      New
      $1,000+/hour
    • Hamptons Experience the 42ft Cigarette Vortex Yacht in Montauk
      Events in Montauk · 10 guests

      Hamptons Experience the 42ft Cigarette Vortex Yacht in Montauk

      New
      $875+/hour
    • 57’ 2023 Okean + 2 Seabobs in East Hampton, New York
      Events in East Hampton · 12 guests

      57’ 2023 Okean + 2 Seabobs in East Hampton, New York

      New
      $1,750/hour
    • 97ft Guy Couach Mega Yacht Charter in Montauk Harbor, New York
      Events in Montauk · 12 guests

      97ft Guy Couach Mega Yacht Charter in Montauk Harbor, New York

      New
      Superowner
      Best of 2026
      $1,875/hour
      Instant Book
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    Most Popular Fishing Charters in Connecticut

    • Luxury 37’ EdgeWater 370CC Charter – Sag Harbor | Sunset Cruises & Montauk Trips
      Powerboats in Sag Harbor · 12 guests

      Luxury 37’ EdgeWater 370CC Charter – Sag Harbor | Sunset Cruises & Montauk Trips

      New
      $750+/hour
    • 40ft Silverton Convertible Flybridge Yacht in Southold, New York
      Events in Noyack · 10 guests

      40ft Silverton Convertible Flybridge Yacht in Southold, New York

      New
      $250/hour
    • Customized Boating Adventure on the Sound | 25ft Seacraft Pacific Center Console
      Powerboats in Stamford · 6 guests

      Customized Boating Adventure on the Sound | 25ft Seacraft Pacific Center Console

      New
      $300/hour
    • Enjoy Fishing or Cruising on a Downeast-Style Boat
      Fishing in Branford · 6 guests

      Enjoy Fishing or Cruising on a Downeast-Style Boat

      5.0
      $190/hour
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    Recent Reviews in Connecticut

    Top Sailboat Rental Locations in the United States

    How To Book on Getmyboat

    4.9 out of 5! • 500,000+ reviews
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      Browse

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      Inquire & Book

      Found one you like? Send a rental inquiry with your preferred trip details, and you’ll receive an offer from your captain to book.

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      Enjoy

      Coordinate a pick-up place and time, meet your boat captain, and get out onto the water!

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