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 sail on beautiful Chesapeake Bay!
  • Enjoy a 1.5 hour sail into the open Chesapeake from historic and scenic Rock Hall harbor
  • "Best of Annapolis & Eastern Shore" in 2011 and voted #1 Tour of the Bay by What's Up Eastern Shore magazine
  • Sail aboard the Crab Royale, an Irwin 40 MKII sloop designed with a spacious deck and an ample supply of cushions for maximum comfort
  • Perfect experience for sailing novices or old salts!

More detailed description >


There really is nothing like taking in the views from a beautiful sailboat as you glide across the water. This is your chance to get out and enjoy a special moment on the Chesapeake.

You'll be sailing from the Sharp Street Pier in historic and scenic Rock Hall harbor. Once you set sail your Captain will sail you into the open Chesapeake Bay.

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

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

There's no better way to spend the day!

Key Info >

Essential Information:

  • Participants must be physically capable of boarding and deboarding the boat from a dock
  • The Chesapeake Bay Sailing Cruise is not wheelchair accessible
  • Includes complementary water and soda, and you may bring along your own alcoholic beverages and snacks
  • Gratuity for your captain and crew are not included and are appreciated if you enjoy your experience

This cruise is approximately 1.5 hours.

Maximum Participants:
You will be accompanied by other tour participants, with a maximum of 6 passengers per boat.

This experience is only for those on the boat.

Weather Dependent:
This experience is weather dependent. 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 1 week notice to your experience provider. Failure to appear on your booked date or to reschedule in accordance with these terms 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 21, 2017

  • 5

  • Philadelphia

"Perfect day for a sunset sail! The boat operators were great, very efficient and friendly."

  • Chesapeake Bay Sailing Cruise

  • June 14, 2017

  • 5

  • Philadelphia

"It was a wonderful trip! Captain Mark and First Mate Suzanne were wonderful!"

  • Chesapeake Bay Sailing Cruise

  • October 20, 2016

  • 5

  • Philadelphia

"The experience was a gift from my partner for my 44th birthday. Everything was perfect: the day, the weather and the sail."