Chesapeake Bay Sailing Cruise

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  • Hop on board for a truly memorable 1.5-hour sail on the Chesapeake Bay Sailing Cruise!
    • "Best of Annapolis & Eastern Shore" in 2011 and voted "#1 Tour of the Bay" by What's UpMagazine
    • Sail aboard the Crab Royale, an Irwin 40 MKII sloop designed with a spacious deck and plenty of seating
    • Kick back, relax and enjoy spectacular views of Chesapeake Bay!

Location & Availability

  • Location(s):
    Rock Hall, MD


    April - June:
    Daily - 1 hour prior to sunset

    July - Labor Day:
    Daily - 10:00 AM, 12:00 PM, 2:00 PM, 4:00 PM & 1 hour prior to sunset

    Labor Day - End of October:
    Monday through Friday - 1 hour prior to sunset
    Saturday & Sunday -  10:00 AM, 12:00 PM, 2:00 PM, 4:00 PM & 1 hour prior to sunset


Full Description

  • Full Description:

    Set sail from the Sharp Street Pier in historic Rock Hall harbor for a beautiful afternoon on the Chesapeake Bay!

    Sail aboard the Crab Royale, an Irwin 40' sloop designed to comfortably accommodate up to 6 passengers. This fast and stable classic has a spacious deck and an ample supply of cushions, just right for novices as well as old salts of any age.

    Your hosts will provide complimentary beverages such as water and soda and you are free to bring along your own selection of alcoholic beverages and snacks if you'd like.

    Take in spectacular views as you glide along the water on the Chesapeake Bay Sailing Cruise!

    Essential Information:

    • Participants must be able to board and depart the boat from the dock with little to no assistance
    • Includes complimentary water and soda
    • Participants are able to bring their own alcoholic beverages and snacks on board

    Approximately 1.5 hours

    Maximum Participants:
    You will be accompanied by other participants with a maximum of 6 passengers on the boat.

    This experience is only for those on the boat.

    Weather Dependent:
    This experience is weather dependent. In the event your experience is canceled due to inclement weather, you will reschedule directly with the experience provider. Always contact the experience provider with any questions regarding weather conditions.

    What to Wear:
    It is recommended to wear layered clothing, rubber-soled shoes, sunglasses and a hat.

    Booking Information:
    For this experience, it is recommended to request bookings 14 days in advance.

    Cancellation Policy:
    Prior to scheduling/booking a date for this experience, Cloud 9 Living's standard return and exchange policy shall apply. Once you have scheduled a date and received a booking confirmation, no exchanges or cancellations are allowed. Rescheduling is allowed with 7 days notice to your experience provider. Failure to appear on your booked date or to reschedule at least 7 days prior will result in the loss of the value of your experience.

    Experience ID:




Reviews (19)

    • Chesapeake Bay Sailing Cruise

    • October 20, 2016

    • 3-half

    • Washington DC

    • "Very nice and easy sail."

    • Chesapeake Bay Sailing Cruise

    • July 26, 2016

    • 5

    • Washington DC

    • "Husband and wife captains were great. Very friendly. Excellent sailing on the Chesapeake!!!"

    • Chesapeake Bay Sailing Cruise

    • November 09, 2015

    • 4-half

    • Washington DC

    • "Sailing on the Chesapeake Bay was an opportunity we did not want to pass up, and it was a great decision. The weather was perfect. The guides were very friendly and extremely knowledgeable, as well as experienced. We will do it again next season and brings friends along next time."