We use cookies to improve your browsing experience.

And dolphins make us happy. Find out more about our cookies policy here.

GetMyBoat Logo

    Browse Annapolis Boat Rentals

    Average of 394 reviews in this area.
    1 - 18 of 36 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

    "3 BuOYS" Regal 38 SAV
    hour$575
    Super Owner10 guests

    "3 BuOYS" Regal 38 SAV

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

    "Imi Ola" Seawind 1260

    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

    Rent this 300 Sea Ray Cuddy Cabin Cruiser in Edgewater, MD
    hour$200
    6 guests

    Rent this 300 Sea Ray Cuddy Cabin Cruiser in Edgewater, MD

    Awesome Savannah SS21 Center Console Fishing in Chester
    hour$100
    10 guests

    Awesome Savannah SS21 Center Console Fishing in Chester

    2021 Tahoe T-16 Bowrider in Glen Burnie, Maryland
    hour$120
    4 guests

    2021 Tahoe T-16 Bowrider in Glen Burnie, Maryland

    21' Center Console Cruises in Chesapeake Bay, Annapolis MD
    hour$100
    10 guests

    21' Center Console Cruises in Chesapeake Bay, Annapolis MD

    36 results

    Boating Guide - Annapolis

    Annapolis Boat Rentals

    Annapolis is a great place for boat rentals. The city is a big boating hub, with hundreds of stunning motor yachts, sailboats, and more. As the sailing capital of the United States, it stays true to its name with beautiful wooden schooners and sailboats cruising in and out of the many ports around Annapolis. A visit to this city isn’t complete without time spent on a boat exploring the beauty of Chesapeake Bay. Rent a motor yacht or sailboat charter while in Annapolis and spend hours cruising and touring. A boat charter can take you to all the great highlights, seeing the skyline from the perspective of the water.

    Annapolis Boat Rental FAQs

    How much does it cost to rent a sailboat for a day in Annapolis?

    Renting a sailboat for a day in Annapolis starts at $350 a day for an Oceanis Cruising Monohull and goes up to $2,100 a day for a Lagoon Cruising Catamaran.

    How much does it cost to rent a boat for a week in Annapolis?

    Renting a boat in Annapolis starts at $100 for a sailboat and goes up to $1,600 for a motor yacht rental.

    Can you sail in Annapolis without a License?

    No, you do not need a license to rent a boat or sail in Annapolis. With GetMyBoat you can rent a boat that includes a licensed captain so that you can enjoy your time on the water. If you want to captain the boat yourself you will need to at the very least have a Boating Safety Certificate. Be aware that owners will have a checkout process to test your competency with their boat, so if you question your ability even if you have your boating safety certificate it is best to go out with a captain.

    When does the boating season start in Annapolis?

    While boating season can vary a bit depending on the weather it usually starts near the tail end of April and ends in September.

    GetMyBoat customer reviews for boat rentals in Annapolis.

    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. MH
      Melissa
      Charter the 60' Sea Spirit Motor Yacht in Annapolis, Maryland

      Captain Steve and his crew went out of their way to help make my husband’s 60th birthday party a big success!! They were especially attentive and helpful to our guest in a wheelchair with the boarding and and de boarding process. They ensured that we had everything needed during the party and were very kind and welcoming. Several guests commented that they appreciated the beautiful views during our voyage and drinks prepared in the bar by the crew. We had food catered and delivered which worked out well. I’d recommend you ask about any additional costs prior to booking since there were dockage and other miscellaneous fees in addition to the fee paid to Get My Boat.

    3. 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!!

    4. Joanna
      Joanna
      Beneteau 41ft Sailing Charter in Annapolis, Maryland

      We had a great time time w/ Captain Gus. He is a very experienced sailor. We were a party of 7 in town for Commissioning Week. It was our first time sailing.

    5. 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.

    6. JB
      Jasmine
      Sea Ray 450 Sundancer Luxury Cruising Yacht near Annapolis MD

      Rented to celebrate my birthday and had an amazing time! The captain was fun and made sure to communicate thoroughly with us. It was an ideal experience

    GetMyBoat has 36 listings for boating experiences in Annapolis with 394 reviews.

    Search Annapolis