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Chesapeake Bay Sailing Cruise

Rock Hall, MD

Item #: WAT-BAL-0020
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Hop on board for a truly memorable 1.5-hour sail on the Chesapeake Bay Sailing Cruise!

  • Experience provider has been awarded 1st place in Chesapeake Magazine's 2019 "Best of the Bay", "Best of Eastern Shore" in 2017, and has received 6 consecutive Certificates of Excellence from Trip Advisor
  • Sail aboard the 43' Island Girl, with a spacious deck, a large cockpit area, and best of all a full cockpit enclosure for shade and protection from less than ideal weather
  • Set sail from the Sharp Street Pier in historic Rock Hall harbor for a beautiful afternoon on the Chesapeake Bay
  • Perfect experience for sailing novices or old salts!
Rock Hall, MD
When Do I Choose A Date?
If giving as a gift, your recipient can choose a date at their convenience; otherwise, you can choose one after checkout.

May through Labor Day:
Daily - 10:00 AM, 12:00 PM, 2:00 PM, 4:00 PM & 1 hour prior to sunset
Labor Day through end of September:
Daily - 10:00 AM, 12:00 PM, 2:00 PM & 1 hour prior to sunset

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  • All available dates have for this season have passed or sold out. Dates for the upcoming season will be posted as soon as they are available. To see a list of this past year's dates for your reference, please click here
    Option & Pricing:
    Please select an option above.
    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
    Experience Provider Info
    Complete information for your Experience Provider, including contact information, will be included on your booking confirmation email once you or your gift recipient have scheduled the experience. Our Product Management team handpicks top-rated experience providers, removing the guesswork for you and ensuring your peace of mind.
    Maximum Participants
    There is 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.

    For this experience, our partners are taking extra measures to help prevent any potential spread of COVID-19. These measures include options for private sails (to temporarily limit group size and the mixing of guests). Seating will be spread out in accordance with social distancing guidelines. Additionally, frequently touched surfaces will be sanitized thoroughly between cruises. Our partners kindly request that each guest wear a face covering when boarding and exiting the boat but are not requiring them while on board.  If you have been ill, not feeling well, or have been around anyone else who has been ill during the two weeks prior to your reservation, please let our partners know so that they can reschedule your cruise.

    Is this a private charter or cruise?
    No, you will be joined by others on the cruise with a maximum of 6 passengers.
    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.
    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.
    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.

    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.

    Experience Vouchers that have not been redeemed can be returned hassle-free within 30 days.  All refunds will be made to the original purchaser.

    Experience Vouchers that have not been redeemed can be exchanged for anything else in our marketplace at any time.  If you choose to exchange for an experience that costs more, you'll simply have to pay the difference.  If you choose to exchange for an experience that costs less, you'll have a credit towards your next booking with Cloud 9 Living.

    Cancellation Policy

    Once you have scheduled a date and received a booking confirmation, no exchanges or cancellations are allowed. Rescheduling is allowed with 7 day's 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.

    Customer Reviews
    (36 reviews)
    View More Reviews:
    “My husband and I received an adventure gift (Cloud 9) from family for Christmas. After a very busy summer, I thought we needed a break. This sailing trip seemed like a good choice and I was absolutely right! Captain Mark and Suzanne were very attentive while providing a relaxing and smooth ride (yes, we dozed a little!). We will most assuredly return for more rides and recommend the Island Lady and crew to friends and family! Thanks Captain Mark and Suzanne!”
    Response from Cloud 9 Living
    Hi Tamara!  Thank you so much for sharing!  You are so right, sailing is certainly the perfect way to spend a much needed break. Captain Mark and Suzanne are truly one in a million, and they will be so excited to hear that your sail was well-enjoyed! Snoozing on the water -- Dreamy!  We can't wait to get you out sailing again next time you're looking for a little R&R! Best, Sophia
    “We had an absolutely wonderful, relaxing cruise. The bay was beautiful, the sunset amazing, the captain friendly, informative and entertaining.”
    Response from Cloud 9 Living
    Hi there Irene,  I am overjoyed to hear that all of the details for a perfect evening fell right into place! It certainly is hard to beat those views, a picturesque sunset, and great crew members! Hoping we can get you out on another incredible experience. Best, Sophia
    “We had a lovely time on the cruise! Would definitely do again and recommend to others!”
    “Great crew! Relaxing time!”
    “We had an awesome time! Captain Mark was fun and informative. The sail was beautiful even though the weather was not great!”
    “We had great time on the sail boat. Host were very nice. I would recommend it to anyone”
    “Couldn’t have asked for better weather to enjoy a beautiful sunset cruise! 6 passengers max, provided a very comfortable lexperience. Captain Mark was professional, funny, and very knowledgeable. His first mate was also very friendly and the perfect hostess offering margaritas and other non alcoholic beverages. Highly recommend sailing with the Blue Crab!”
    “Captain Mark was amazing. Overall the trip surpassed my expectations. The ship was very comfortable and Captain Mark was very hospitable. He made us feel very welcome. Thank you for making this an unforgettable experience.”
    Response from Cloud 9 Living
    Hi Eliana,   Wow! We are so incredibly honored to be a part of a memory that will truly last a lifetime! Captain Mark is one of the finest in the industry, and we will be sure to pass along the kind words. Let us know when you are ready to get out on another adventure and make more memories!    Best, Sophia
    “It was very pleasant. There wasn't any wind to speak of so most of our sailing trip was spent motoring. But, the captain kicked in his backup plan and took us for a tour of Swan Point which was interesting.”
    “Peaceful, easy to find the boat, easy to board, fully equipped; mark was really personable and a good guy all the way around. VERY peaceful. My wife and two daughters went, there were two women who also sailed with us at the same time. We really, really liked it.”
    “From start to finish we really enjoyed ourselves! We were running a little late and they were still able to accommodate us. We drove almost two hours, caught traffics on our way, and got pulled over on our way there. Nonetheless, they waited and even offered complimentary beverages. Even after the boat had difficulties coming back in they displayed remarkable service. Their friends were kind enough to tow us back in. Superb customer service! Definitely recommend. Joanna Lopez”
    “We had a great time. Mark and Suzanne were very nice and the trip was great. I recommend this sailing experience to everyone. Very relaxing. Thanks”
    “Wow. Just... wow!”
    “Overall a very good afternoon sail. Would have liked it better if the Captain could have raised the main sail.”
    “Capt Mark was awesome - he made sure everyone was comfortable and enjoying the sail. He's an experienced sailer and you can tell has a passion for it. We thoroughly enjoyed this excursion and would happily do it again.”
    Response from Cloud 9 Living
    Hi Kori,  We are thrilled to hear you enjoyed your sail! We love Captain Mark, and will be sure to let him know that his expertise and passion for sailing did not go unnoticed! We hope to get you sailing again soon!  Best,  Sophia
    “The ships captain was very engaging and allowed anyone who wanted to to participate in the actual sailing of the vessel.”
    Response from Cloud 9 Living
    Hello, Tom! It sounds like you had an amazing time! Glad you got to take a turn on the sail. Cheers,  Kasia
    “Great sail with a friendly host who answered questions and offered insight for the area”
    “My wife and I were provided with a Christmas gift to sail with Blue Crab Chesapeake Charters and we had a most wonderful time. It was a very peaceful and enjoyable time. The Captain and First Mate were excellent!”
    “These trips are great! Mark is a great captain and very friendly. We've gone on trips with him twice now (1 sunset, 1 day cruise) and loved every second. We bring a cooler with wine and snacks and just relax. Will absolutely go again!!”
    “This was a very relaxing experience. My husband and I got this as a wedding gift. The weather was great and we got to just relax on the boat.”
    “An absolutely amazing experience! The boat was beautiful and the crew was very friendly. Sailing to see the sunset was lovely. I definitely will do it again and maybe with a group of friends.”
    “We had a wonderful time! Suzanne was extremely patient when I called multiple times for a weather check. Captain Mark was a delightful guide who pointed out landmarks along the way. We had another couple and a single woman with us as well as my husband’s 90 year old mother. Captain Mark was so gracious with her and helped her on and off the boat. After the cruise, we enjoyed a delicious meal at Wateman’s Crab House. We highly recommend Captain Mark and Suzanne’s Chesapeake Sailing excursion.”
    “Mark was an experienced sailor and a wonderful host. I would highly recommend sailing with Blue Crab.”
    “Perfect day for a sunset sail! The boat operators were great, very efficient and friendly.”
    “Had a fantastic afternoon on the bay. Next time we will invite another couple to enjoy it with us. Mike and Suzanne were the perfect guides.”
    “Not only were we fortunate to have the most perfect and beautiful sunset, but we also had the perfect weather and company. It was my birthday and I had a wonderful evening. I met some awesome new friends, who helped celebrate my birthday with a BANG! I intend to do this yearly at different times to get different experiences. Thank you for a great evening.”
    “I cannot say enough good things about this trip! Such amazing and friendly people both sailing the boat and also along for the ride! I have already recommended this trip to a coworker for her anniversary, and I also plan to bring a visiting friend in the future. ”
    “Absolutely amazing!! We had high expectations and it totally surpassed them!”
    “What a wonderful experience!! Captain Mark and First Mate Suzanne were very gracious hosts, and our party of four thoroughly enjoyed our time on the water. Would definitely book this experience again!”
    “Enjoyed sailing with Captain Mark and Suzanne, who were both very professional, with a bit o' the whimsy, teaching some teens on board to navigate with confidence and providing a memorable margarita!”
    “We received this as a wedding gift! What a great gift. It took us two years to use it, but worth the wait. So nice to receive a gift that didn't expire.”
    “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. ”
    “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. ”
    “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. ”
    “We loved it!!!”
    “Enjoyable cruise with Capt. Mark and 1st Mate Suzanne.”

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