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Number of People: 6
Duration: 1 hour and 30 minutes


All hands on deck! Get ready for the ultimate sailing adventure aboard the 43' Island Girl on the picturesque Chesapeake Bay! Whether you're a seasoned sailor or a total landlubber, this 1.5-hour private sail for up to 6 passengers promises to be the experience of a lifetime!

🌅 Get ready to witness the breathtaking beauty of the Chesapeake Bay at sunset during this 1.5-hour private sail on the 43' Island Girl

🍹 Enjoy complimentary water and soda, or bring your own choice of alcoholic beverages and snacks to enjoy while taking in the stunning views

🚣‍♂️ With a spacious deck and a full cockpit enclosure providing shade and protection from the weather, you can relax and unwind in comfort during the sail

⚓️ Trusted provider who won "Best of the Eastern Shore" for 2023 per What's Up Eastern Shore Magazine


When do I choose a date?

After purchase, you can request your preferred dates and times by following the instructions in the email you receive. If it's a gift, the recipient will also get an email with booking instructions.

May-September 10:00am, 12:00pm, 2:00pm, 1 hour prior to sunset, and at sunset

Practical information

Any restrictions to participate?

  • Age: All age groups are welcome.

Who can you accommodate for?

  • Children: All participants must pay to participate, children included. Children 12 and under will be required to wear a life jacket.
  • Individuals with disabilities: The sailboat is not wheelchair accessible. Participants must be able to board and depart the boat from the dock with little to no assistance.
  • Pets: Sorry, no pets allowed.

What to expect on the day of the experience?

  • Duration: Approximately 1.5 hours
  • What’s included: You will enjoy a 1.5 hour private sailing cruise starting from Rock Hall harbor, sailing into the Chesapeake Bay. Complimentary water and soda will be provided by the captain, and you are welcome to bring your own selection of alcoholic beverages. Please note that red wine is not recommended.
  • Who will be present: You will have a captain with you at all times and your private group of up to 6 people.
  • Spectators: No spectators are allowed, everyone must have a ticket/reservations.
  • Photo/ video: You may take your own photos.

How to prepare?

  • Weather dependency: This experience is weather-dependent. In the event that the 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.
  • Arrival: Plan to arrive 15 minutes in advance.
  • Parking: Parking is available on site.
  • What to wear: Please wear boat shoes or light sole sneakers aboard. Black sole shoes and flip flops are not recommended. Barefoot is best! It is also recommended to wear layered clothing according to the weather.
  • What to bring: A camera, sunscreen, hat and sunglasses are recommended. You are welcome to bring your own food or drink.
  • Restrooms/ lockers/ changing rooms: A bathroom can be found on the boat.

Full description

Experience the charm of a private Chesapeake Bay sailing cruise for up to 6 guests. Depart from Rock Hall Harbor aboard "Island Girl," a 43-foot Morgan sailboat offering comfort and convenience. Enjoy scenic sails into the Chesapeake Bay or Swan Creek, with accommodating hosts and cozy sleeping quarters. It's the perfect way to explore the Eastern Shore of Maryland and create unforgettable memories.

As you soak in the stunning views, you'll be treated to refreshing complimentary beverages like water and soda. Plus, don't forget to bring along your favorite snacks and alcoholic beverages to really make the most of your time aboard.

Returns, exchanges and cancellation

Unused Experience Vouchers can be returned within 30 days for a full refund to the original purchaser, no questions asked.

If you have any unused Experience Vouchers, you can exchange them for anything else in our marketplace, no matter when. If you choose an experience that's more expensive, you'll need to pay the difference, but if you choose one that costs less, you'll receive a credit towards your next booking.

No refunds are allowed once the experience is booked, but you can reschedule up to 7 days before your experience, for a date within a year of the original booking. To reschedule, contact the experience provider directly. No-shows or rescheduling less than 7 days in advance means losing the value of your experience.

Number of People: 6
Duration: 1 hour and 30 minutes
Regular price $252
$252 Regular price Sale price
You save $-252

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Here's what others have to say!



Based on 0 reviews

Jennifer F

My husband received this as a gift, and we absolutely adored it! It was a private sailing experience for the two of us and my in-laws, and it was simply incredible. Captain Mark was an excellent host, providing us with drinks and great conversation during the sail. We learned a lot about the area and his sailing experiences. Additionally, dining at the Waterman's Crab House before and after our sail was the cherry on top. Meeting at the restaurant made everything effortless, and the staff there ensured that we arrived at our boat on schedule.

Elle L

For my dad's Christmas gift, I arranged a voyage with Blue Crab Chesapeake Charters. It was a fantastic experience that exceeded our expectations, from the boat itself to the refreshments, and especially the fantastic company of Captain Mark and Suzanne. I strongly recommend this, and I plan to reserve another trip with them in the near future.

Phillip H

We had a fantastic private 90-minute cruise with Captain Mark and 1/M Suzanne on the Island Girl from Rock Hall to Chesapeake Bay. They were great hosts, and we even got a refreshing surprise when a wave splashed on board. Can't wait to do it again!