Great sailboat rentals near Rock Hall, Maryland.

Average of 43 reviews in this area.
7 listings
Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland
hour$150
Chesapeake BayCruising Monohull
Super Owner6 guests

Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

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

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

Overnight Cruise for up to six people in Rock Hall, Maryland
night$1,199
Chesapeake BayCruising Monohull
6 guests

Overnight Cruise for up to six people in Rock Hall, Maryland

Weekend Sailing Charter in Rock Hall, Maryland
day$1,350
Chesapeake BayCruising Monohull
6 guests

Weekend Sailing Charter in Rock Hall, Maryland

Sunset Cruise in Rock Hall, Maryland onboard Catalina 425 Sailboat
hour$200
Chesapeake BayCruising Monohull
6 guests

Sunset Cruise in Rock Hall, Maryland onboard Catalina 425 Sailboat

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

Get ready for a fun adventure when you hit the open water onboard a sailboat in Rock Hall, 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. Rock Hall, 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 Rock Hall.

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

    We had a great afternoon sail with Captain Joe, followed by some swimming off the boat at the end of the day. Our three kids had a great time, from some time at the helm, hanging out on the bow, and swimming at the end of the day, we all enjoyed every moment. Captain Joe was attentive, a great communicator, and flexible in figuring out the itinerary. I highly recommend a sail on the bay with Captain Joe!

  2. JG
    Jose
    Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

    It was our first time on a sailboat. Captain Joe communicated what to expect and made us feel very comfortable. He was friendly, and the boat was very nice.

  3. KL
    Kia
    Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

    Captain Joe was absolutely amazing, everything was as described. Booking and communication were excellent and we are looking forward to another trip.

  4. TS
    Tatsiana
    Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

    We can't wait to come back and experience new marine adventures with Captain Joe and his Sol Searcher again. According to my 13 y.o. kid, it was one of the best birthdays she has ever had. The sailboat is so beautiful, spacious, and comfortable. Captain Joe was very hospitable, friendly, and considerate. He told us a lot about sailing and made my daughter's dream come true - we saw a rare and hardly accessible caisson structure Baltimore Harbor Lighthouse. It was amazing! Upon return we had some delicious brownies baked by Joe's wife. Always appreciate a personal touch. We felt very welcome and had a great time! Highly recommend this captain and his gorgeous sailboat!

  5. KC
    Kyle
    Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

    Captain Joe is an excellent sailor and has great communication. When I booked the private charter I reached out to let Joe know that I would be proposing on his vessel, we had a few date changes that joe worked through with me flawlessly. The pictures on the listing do not do this boat and captain justice! 10/10 would recommend!

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

    We had an amazing sail with Captain Joe! The boat was beautiful and spacious, and Captain Joe was very attentive to all of our needs. Can’t wait for another sail in the future!! Would definitely recommend this experience with Captain Joe!