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    Find Sailing Charters Near You

    Average of 2,895 reviews in this area.
    1 - 18 of 180 listings
    Sip and Sail D.C.
    hour$700
    6 guests

    Sip and Sail D.C.

    22' Sea Ray Powerboat for 6 people in Washington, District of Columbia
    hour$155
    6 guests

    22' Sea Ray Powerboat for 6 people in Washington, District of Columbia

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

    "Imi Ola" Seawind 1260

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

    2020 Fountaine Pajot Astrea 42' in Key West FL

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

    Charter 44' Orana Cruising Catamaran In Deale, Maryland

    41' Lagoon Cruising Catamaran in Maryland, United States
    hour$349
    12 guests

    41' Lagoon Cruising Catamaran in Maryland, United States

    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA
    hour$150
    Super Owner6 guests

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

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

    Beneteau 41ft Sailing Charter in Annapolis, Maryland

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

    Annapolis Sailing on a 34' Beneteau Sloop!

    Get away for a day or weekend! Charter 44' Catalina Sailboat!
    day$490
    6 guests

    Get away for a day or weekend! Charter 44' Catalina Sailboat!

    Sailing Charter with USCG Licensed Captain
    hour$150
    6 guests

    Sailing Charter with USCG Licensed Captain

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

    Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

    Fully Crewed Sailing Cruises Aboard 41' Sailboat in Rock Hall, MD
    hour$125
    4 guests

    Fully Crewed Sailing Cruises Aboard 41' Sailboat in Rock Hall, MD

    34' Hunter Cruising Monohull In Rock Hall, Maryland United States
    night$220
    4 guests

    34' Hunter Cruising Monohull In Rock Hall, Maryland United States

    Charter 41ft S/Y Selina II Sloop in St. Michaels, Maryland
    hour$349
    6 guests

    Charter 41ft S/Y Selina II Sloop in St. Michaels, Maryland

    Sunset Champagne Cruise on the Chesapeake Bay
    hour$399
    6 guests

    Sunset Champagne Cruise on the Chesapeake Bay

    100+ results

    Boating Guide - Sailing

    Set sail with GetMyBoat - enjoy a sailing charter.

    Hit the open water in style on a sailing charter. Sailing charters with a professional captain are a relaxing way to get on the water and travel by wind power. A sunset sailing cruise, cocktail cruise, or other sailing adventure can make for the perfect experience on a lake or the ocean. Most larger sailboats (typically 18+ feet) also use an engine for longer sailing trips. GetMyBoat has all types of sailing charters and you can build a custom itinerary to plan the sailing holiday of your dreams. From hourly, half-day, full-day or overnight sailing excursions, you are sure to create memories that will last a lifetime.

    Using GetMyBoat to rent your next sailboat.

    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 safety checks on each rental transaction.

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

    Things to consider when booking a sailboat rental or charter.

    • Sailboats range in size and carrying capacity, so check with the captain to make sure the boat you pick will meet your needs.
    • If you want to learn some sailing techniques, ask about instruction or lessons while you're onboard.
    • Any doubts about booking your sailing adventure? No problem! Simply message the captain and ask any questions you may have.

    GetMyBoat customer reviews for Sailing in this area.

    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 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. 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!!

    6. AH
      Angela
      Charter this 42ft Sailboat in Edgewater, Maryland and sail on beautiful Chesapeake Bay and beat inflation. Same prices this year as last!!

      Captain Bill was absolutely marvelous!! The trip was amazing!! My guest and I chartered a three hour venture and had the wonderful adventure! We celebrated my cousin’s birthday and everyone was elated to ride with such a great captain! He went above and beyond to make sure we had a joyous occasion! His personality was second to none!! I extremely recommend you charter him for your next boat ride!! You will not be disappointed!!

    GetMyBoat has 180 listings for Sailing experiences in this location with 2,895 reviews.

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