Great sailboat rentals near Baltimore, Maryland.

Average of 105 reviews in this area.
9 listings

Step onboard a sailboat for an unforgettable experience in Baltimore, Maryland.

Get ready for a fun adventure when you hit the open water onboard a sailboat in Baltimore, Maryland. 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. Baltimore, Maryland is a wonderful sailboat rental destination.

Using GetMyBoat to rent your next sailboat.

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

GetMyBoat customer reviews for Sailing in Baltimore.

  1. SR
    Steven
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    The vast amount of 5 star reviews are a testament to Captain Alberto's spectacular service and expertise. We booked a trip for my girlfriend's birthday and it was absolutely perfect. I'd rate 10 stars If I could. We will definitely be going back!

  2. JB
    Jenna
    Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

    Captain Joe was an incredible host and captain on our early Spring sail. He was kind, thorough, and hospitable with delicious treats to snack on. He knew the area and would point out interesting facts as well. He was casual, easy to talk with, and overall very easy going. We highly recommend Captain Joe for you sailing adventures. A wonderful way to spend the afternoon away from the laptop and enjoying the fresh air! Thanks, Joe!

  3. PW
    Phyllis
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    Captain Alberto is the best! The boat was very nice and I learned a lot about sailing. We enjoyed the experience. Thanks.

  4. CB
    Cathy
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    We had a wonderful time sailing with Captain Alberto and his wife Grace! My husband and I and two of our friends went for an afternoon cruise as a birthday celebration. The boat was beautiful and they were friendly and gracious hosts. I was interested in learning more about sailing and Captain Alberto (an experienced sailing instructor) was a great teacher. Captain Alberto was also very responsive and helpful when we were making the arrangements for the trip. We hope to have an opportunity to do this again, and highly recommend a trip with Captain Alberto!

  5. KH
    Karen
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    Our group of 6 friends enjoyed a terrific sunset cruise on Captain Alberto's boat. Captain Alberto is clearly an experienced sailor. He and his lovely wife were both very welcoming and we really enjoyed their company. Overall it was a wonderful evening and we all highly recommend it!

  6. SL
    Sarah
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    I booked this trip as a surprise birthday present for my fiancé! I invited a few of his friends and they all had a great time hanging out and learning a little about sailing. Captain Alberto and his wife were great and very knowledgeable. We would definitely recommend to anyone!