Chesapeake Bay Sailing Cruise

Rock Hall, MD

From: $70
Item #: WAT-PHI-0021

Hop on board for a truly memorable 1.5-hour sail on the Chesapeake Bay Sailing Cruise!

  • Experience provider has been awarded "Best of Eastern Shore" in 2017, and "Outstanding Business of the Year" in 2016 by Kent County Chamber of Commerce, 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!

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Summary

Hop on board for a truly memorable 1.5-hour sail on the Chesapeake Bay Sailing Cruise!

  • Experience provider has been awarded "Best of Eastern Shore" in 2017, and "Outstanding Business of the Year" in 2016 by Kent County Chamber of Commerce, 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!
Location
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.
Availability:

April 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

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

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

Sail aboard the 43' Island Girl, designed to comfortably accommodate up to 6 passengers. This fast and comfortable center cockpit cruiser 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 welcome 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 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
Duration
This cruise is 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
You will be accompanied by other tour participants, with a maximum of 6 passengers per boat.
Spectators
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

Once you have scheduled a date and received a booking confirmation, no exchanges or cancellations are allowed. Rescheduling is allowed with 1 week's 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.

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.
This experience has a customer rating of 5
based on 34 reviews.
View More Reviews:
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
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!
Great sail with a friendly host who answered questions and offered insight for the area
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.
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.
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.
Oh my goodness! What a wonderful experience. We were a bit concerned about the weather not cooperating, but were so lucky to have had such beautiful weather conditions for our cruise. We were with two other couples and enjoyed our time so very much! Suzanne and Mark could not have been more gracious! Highly recommend their service! Hard to find such personal care like this anymore! 5 star +++
Response from Cloud 9 Living
Hey Karen, Thanks for your lovely review! We love working with Suzanne and Mark, so I'm very happy to hear that you all enjoyed your time on the water with them as well. It will make their day to read your kind words. What a fun way to spend time with friends!  Thanks again for your time and have a wonderful week!  Best, ​Brooke
We had a great time on our sunset cruise. The seas were abnormally rough that afternoon, but our guide made us feel safe the entire time and made sure we had a fun experience. The views were amazing. And the (self-designated) after party at Waterman's was great. :) I would definitely go back!
Mark and Susan were perfect hosts. They were friendly and welcoming but also respected the time when all we wanted to do was to take in the sunset views. This was definitely the highlight of our 3 day trip to Maryland.
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.
Perfect day for a sunset sail! The boat operators were great, very efficient and friendly.
It was a wonderful trip! Captain Mark and First Mate Suzanne were wonderful!
The experience was a gift from my partner for my 44th birthday. Everything was perfect: the day, the weather and the sail.
It was wonderful!!!! Would love to go back and bring friends!
Mark and Susan were wonderful hosts. We really enjoyed the opportunity to sail with them and the other guests.
We received a sailboat cruise as a Christmas gift. I booked the trip at the last minute. No problem! Everything was perfect and my wife and I really enjoyed the cruise. Thank you.
Experience was just what we expected!
We had such a great time with Captain Mark and Suzanne. The cruise was awesome and we can't wait to do it again! We'll be telling all our friends about it. I highly recommend it!
Captain Mark was absolutely wonderful! We had our two young girls on the sailing tour with us (ages 6 & 8), and he was so patient. He even let them steer the boat and wear his hat. Great experience -- we'll be returning for sure!!
Captain Mark and his wife where wonderful. Great experience and a beautiful day on the water.
We had a great time! Mark and Sue were so nice and even let my boyfriend navigate the boat for a bit. With us having 4 kids, it's hard to ever have some R&R. This experience was just that. Definitely planning on a repeat trip.
The sailing cruise was amazing! We couldn't have asked for anything better. Captain Mark and Susan were great hosts and the weather was perfect (we had been in contact all morning with threats of thunderstorms canceling our trip). Highly recommend this experience! I can't wait to go again! Thank you again to Captain Mark and Susan!!
Great sailboat cruise. The captain was great and we had a wonderful time.
Captain Mark and his wife were very accommodating and very nice people. We had a great time on their sail boat and it was a very relaxing experience.
We really enjoyed the sailing trip and would recommend it to anyone. The captain and his mate were really knowledgeable and very freindly.
Captain was very accomodating with re-scheduling our Sunset cruise that got rained out at the last minute. They were able to schedule us for the very next day early in the am since we had to check out of our hotel and we were due to leave the area.
Everything went very well on our sailing trip. We met the captain, embarked and set off with no issues. The captain and his first mate were very friendly. They played great music, served drinks, told stories and made the overall experience very enjoyable. It helped that the weather was absolutely perfect and there were enough clouds in the sky to make the sunset interesting. Overall, the experience was wonderful and I would recommend it for anyone who would like a fun, relaxing jaunt on the Chesapeake!
I gave my parents a Blue Crab Chesapeake Charters chartered sailing experience for Mothers' and Fathers' Day. We had such a lovely time - we got lucky with amazing weather, the captain and first mate were a pleasure, and it was such a relaxing trip. We just wish that we'd had more time - so we'd definitely consider booking this experience again!
The cruise was a gift to my husband from our daughter. Really didn't know what to expect. What we got was a wonderful experience!!!! The Captain and his first mate were great hosts!!!!. We had all kinds of weather(it added to the fun),and were rewarded with a rainbow!!! My husband was able to "help" the captain. He LOVED IT!! Would recommend this adventure!!
We had a nice waterside view of the surrounding area. There wasn't much wind, but my wife prefers that. The hosts were wonderful. The boat was comfortable and well sailed. Looking forward to next year!
We had a lovely, relaxing evening on Captain Mark's boat.
Beautiful tour. Great creW!
Beautiful sailing day with plenty of wind, and a wonderful sunset on the Chesapeake Bay.

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