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Duration: 1 hour and 30 minutes


Get ready to set sail on the beautiful Chesapeake Bay for a 1.5-hour cruise aboard the 43' Island Girl! Whether you're a seasoned sailor or a first-time sailor, this cruise is the perfect way to experience the beauty of the Chesapeake Bay in Rock Hall, MD.

🌅 Take in the breathtaking scenery as you sail along the Chesapeake Bay

🥤 Enjoy free water and soda onboard to keep you refreshed throughout the journey

🍔 Feel free to bring your favorite snacks and alcoholic beverages along to make the experience your own

⛵ Set sail from the historic Sharp Street Pier in Rock Hall harbor, and relax in style


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-end of September

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 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 up to 6 other 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

During the cruise, you will be able to take in the scenic views and relax while enjoying complimentary beverages such as water and soda. Feel free to bring along your own snacks and alcoholic beverages as well.

The sail will depart from the Sharp Street Pier in historic Rock Hall harbor, and you will have the chance to explore the bay in comfort aboard the Island Girl, complete with a full cockpit enclosure for shade and protection from less than ideal weather.

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.

Duration: 1 hour and 30 minutes
Regular price $44
$44 Regular price $45 Sale price
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Here's what others have to say!



Based on 0 reviews

Adam H

Captain Mark was amazing during our sailing trip. Despite the windy weather, he kept both my 80-year-old mother and me engaged throughout the entire trip. As experienced sailors, we had a great time and we look forward to returning in the spring. Thank you, Captain Mark, for an unforgettable experience!

Geoff J

A delightful Chesapeake afternoon! Can't wait to experience it again!

Declan T

Had an amazing experience with Captain Mark! The trip and weather were absolutely perfect. Having the boat all to ourselves was fantastic, especially since we were a family of 6.

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