Chesapeake Bay Sailing Cruise

From: $70   Region: Baltimore (View all 44 Baltimore experiences)


Rock Hall, MD


April through June

Daily - 1 hour prior to sunset

July through October

Daily at 10:00 AM, 12:00 PM, 2:00 PM, 4:00 PM and 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, just right for novices as well as old salts of any age.

Your hosts will provide complementary 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.

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. 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 on the 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 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'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 may be joined by others on the cruise, with a maximum of six passengers.
  2. How long is the cruise and where do we go?
    You'll be cruising for approximately 1.5 hours and will set out from Rock Hall harbor and sail into the open Chesapeake Bay.
  3. Are refreshments included? Can I bring beer or wine?
    Complementary refreshments are provided by your host. Feel free to bring along your own selection of alcoholic beverages.

Customer Reviews:

  • Chesapeake Bay Sailing Cruise

  • July 18, 2014

  • 5

  • Baltimore

"We all had a wonderful time. It was a family outing and the Captain gave us a great cruise. The margarita was terrific. Would do it again in a heartbeat. Thanks Blue Crab charters. "

  • Chesapeake Bay Sailing Cruise

  • September 19, 2013

  • 5

  • Baltimore

"Capt Mark was a top notch sailor and his boat was just the right size. We had a wonderful time and will go again next year. "

  • Chesapeake Bay Sailing Cruise

  • July 02, 2013

  • 5

  • Baltimore

"We were unable to book a June cruise thru Cloud Nine. We were told booking began in July and that we needed a 2 week window. We contacted the provider and made arrangements for a June cruise within the next few days. We contacted Cloud Nine who confirmed the booking and sent us the necessary confirmation. "