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    Incredible sailboat rentals in Chesapeake Bay, United States.

    Average of 294 reviews in this area.
    1 - 18 of 24 listings
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA
    hour$150
    Super Owner6 guests

    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland
    hour$150
    Super Owner6 guests

    Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

    "Imi Ola" Seawind 1260
    hour$716
    Super Owner12 guests

    "Imi Ola" Seawind 1260

    J70 Daysailer rental in Hampton
    hour$100
    Super Owner4 guests

    J70 Daysailer rental in Hampton

    Beneteau 41ft Sailing Charter in Annapolis, Maryland
    hour$200
    8 guests

    Beneteau 41ft Sailing Charter in Annapolis, Maryland

    Charter 44' Orana Cruising Catamaran In Deale, Maryland
    day$2,600
    10 guests

    Charter 44' Orana Cruising Catamaran In Deale, Maryland

    Let's Go Sail in Gloucester Point, Virginia
    hour$125
    6 guests

    Let's Go Sail in Gloucester Point, Virginia

    Annapolis Sailing on a 34' Beneteau Sloop!
    hour$150
    6 guests

    Annapolis Sailing on a 34' Beneteau Sloop!

    2020 Fountaine Pajot Astrea 42' in Key West FL
    day$1,795
    12 guests

    2020 Fountaine Pajot Astrea 42' in Key West FL

    24 results

    Boating Guide - Chesapeake Bay Sailing

    Rent or charter a sailboat for a memorable experience in Chesapeake Bay.

    Are you ready for a fun adventure out on the open water onboard a sailboat in Chesapeake Bay? Rent or charter a sailboat with or without a captain and experience the joy of exploring the water by wind power. From hourly, half-day, full-day or multi-day sailing excursions, you are sure to create memories that will last a lifetime. Chesapeake Bay is a wonderful sailboat rental destination.

    Using GetMyBoat to book your next sailing experience.

    Experiencing the water has never been easier thanks to GetMyBoat. GetMyBoat allows you to quickly search, compare prices, submit rental inquiries, and pay for your rental or charter from the convenience of your phone or computer. We offer a secure platform for renters to facilitate a seamless rental transaction. For boat owners, we connect millions of renters to their boat and provide the security and safe checks on each rental transaction.

    Search for the perfect experience now and book your dream day out on the water.

    GetMyBoat customer reviews for Sailing in Chesapeake Bay.

    1. KF
      Kristen
      41' Lagoon Cruising Catamaran in Maryland, United States

      Our group had a great time out on the water with Captain Jess and his catamaran! We cruised around the South River and found a perfect spot to anchor out for swimming. Could not recommend Captain Jess and his boat more. We will definitely be back!

    2. EG
      Elizabeth
      41' Lagoon Cruising Catamaran in Maryland, United States

      Captain Jess and his catamaran, Imagine, were absolutely incredible! We had the best day cruising & sailing around the South River and Chesapeake Bay. So hospitable, knowledgeable, and made us feel safe and at ease of the seas! What a beautiful day and an exceptional time. Can't wait to sail on Imagine again! Thank you Captain Jess!!

    3. JW
      Jinli
      38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

      Captain Albert and Grace gave us a very enjoyable and fulfilled sailing trip around Annapolis and the Chesapeake bay. Thanks for their hospitality, and we all appreciate the guided “hands-on” sailing experience.

    4. Bobby
      Bobby
      Charter this 42ft Sailboat in Edgewater, Maryland for upto 6 persons and sail on beautiful Chesapeake Bay and beat inflation. Same prices this year as last!!

      Capt Bill and Jonah were both awesome. The day was perfect. Outstanding company, and we were lucky enough to see Dolphins. 10/10 highly recommend!

    5. TC
      Tiffany
      41' Lagoon Cruising Catamaran in Maryland, United States

      Awesome experience. The boat was well equipped and very clean!

    6. AA
      Amber
      Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

      Captain Joe was awesome and accommodating! Highly recommended and we'll look to him whenever we'd like to go sailing again, thank you!!

    GetMyBoat has 24 listings for Sailing experiences in Chesapeake Bay with 294 reviews.

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