Great sailboat rentals near Baltimore, Maryland.

Average of 55 reviews in this area.
8 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.

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 Baltimore.

  1. SS
    Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

    Joe was absolutely amazing, the yacht was spectacular. It was extremelt clean, spacious, and he did an awesome job with his hospitality & ensuring all of our needs were met. I highly reccommend and will most definitely be returning. We felt right at home here, and didn’t want the trip to end.

  2. MS
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    The whole trip was fantastic! Captain Alberto was easy to communicate with and let us ask a ton of questions about sailing, Annapolis and the whole boat community. He is knowledgeable and we got to help a bit raising the sail and he even let us drive the boat (at the helm) for a bit. We had a wonderful time and will definitely be booking again! Will be recommending this trip to our DC friends too!

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

    I booked this trip for my sister’s bachelorette weekend and it was a hit! Everyone loved it and Captain Alberto and his wife were wonderful tour guides. Next time we are in Annapolis we will be booking another trip!

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

    This experience was amazing! Captain Alberto and his wife were so kind and made our time on the boat really special. We even took a turn driving the boat ourselves! The boat is a great size and has a bathroom and a fridge to store any drinks/food you may bring with you. I cannot recommend this boat enough!

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

    You cannot go wrong by booking this charter. Captain Alberto is a knowledgeable and experienced Captain who knows the Annapolis waters well. Don’t even think twice, book it. So worth it!

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

    We had the most amazing sail even though we didn’t have the most ideal weather. Capitan Joe motored is out to “find the wind” and we were able to enjoy both tranquility and the blissful breeze of a non-thunder cloud. The brownies and fresh raspberries were a nice indulgence as we glided peacefully back to the marina. We can’t wait to go out again!