Chesapeake Bay Sailing Cruise

From: $70   


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

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!

More detailed 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!

Key Info >

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:

View FAQ's >

  1. Is this a private charter or cruise?
    No, you will be joined by others on the cruise with a maximum of 6 passengers.
  2. How long is the cruise and where do we go?
    This cruise is approximately 1.5 hours and sets out from Rock Hall harbor sailing into the Chesapeake Bay.
  3. Are refreshments included? Can I bring beer or wine?
    Complimentary water and soda will be provided by the captain and you are welcome to bring your own selection of alcohol beverages. Please note, red wine is not recommended.
  4. Is the sailboat wheelchair accessible?

    The sailboat is not wheelchair accessible. Participants must be able to board and depart the boat from the dock with little to no assistance.

  5. Is there an age limit?
    There is no age restriction to sail, although all children 12 and under will be required to wear a life jacket.

Customer Reviews:

  • Chesapeake Bay Sailing Cruise

  • June 27, 2017

  • 5

  • Washington DC

"Our guides were absolutely wonderful. They were knowledgeable about all things sailing and were just great people. But we also had some quiet time to relax and enjoy a perfect day on the water. The complimentary margaritas didn't hurt either! Perfect day trip. Would definitely recommend. "

  • 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!!!"