Chesapeake Bay Sailing Trip

Enjoy a Relaxing 90 Minute Scenic Sailboat Ride on the Chesapeake Bay

1 Participant Included - Add More?

About This Experience

General Information hide

Enjoy the beauty of the Chesapeake Bay during an hour and a half sightseeing sailing trip aboard the Island Girl, a classic Morgan 43. This five-star rated experience gift, awarded Best of Eastern Shore, is one of the best things to do on Maryland's beautiful Eastern Shore!

The fun begins in Rock Hall, MD when you meet with the friendly Captain Mark and his first mate Suzanne at the dock. They will welcome you aboard the sailboat and fill you in on the details of this 90 minute sailing trip on the Bay. Once everyone has boarded the boat, it’s time to head out to the open waters. After the Captain has navigated the ship out of the marina into Chesapeake, you and the rest of the guests can take your turn at the helm, help raise the sails or simply sit back and relax and enjoy a complementary beverage. The sun sparkling off of the Bay, the fresh sea air and beautiful views are just a few of the things this popular experience has to offer.

So whether you are looking for the perfect unique gift or fun things to do on the Eastern Shore, this Chesapeake Bay Sailing Trip is the ticket!

Inquire about this Experience

Where It's Located hide

  • Rock Hall, Maryland

Who Is Included hide

The Chesapeake Bay Sailing Trip Experience Gifts Certificate is valid for one participant. There will be up to five additional participants on the sail.

This experience is not suitable for non-paying guests.

When It Is Offered hide

The Chesapeake Bay Sails are offered seven days a week April thru October, subject to availability. May through August sails typically take place at 10:00 AM, 12:00PM, 2:00 PM, 4:00 PM and 1½ hour prior to sunset. April and September through October weekday sails are offered 1½ hour prior to sunset and weekend sails typically take place at 10:00 AM, 12:00PM, 2:00 PM, 4:00 PM and 1½ hour prior to sunset.

How Long Is It hide

The Eastern Shore Sail Boat Rides have a cruise length 1½ hours and a total duration of approximately 2 hours.

Weather hide

The Chesapeake Bay Sailing Trips may be rescheduled by the Captain due to high winds, heavy rain, fog or other inclement weather.

What To Wear hide

Dress comfortably, flat, non-marking rubber-soled shoes and layers are recommended for this sailing adventure.

Additional Information hide

Sails take place on a classic Morgan 43 which is skippered by a USCG-licensed captain and crew. Participation is limited to individuals 3 years of age or older. Children 12 years of age and younger are required to wear a life jacket.

Complimentary ice, water, soda and other beverages are available on the ship.

While motion sickness is possible, it is unlikely and can be reduced by avoiding heavy meal(s) prior to the scheduled sail. All passengers must sign a release form.

Gratuity for the Captain and Crew is not included and may be extended following your sail.


Reservation Information hide

All changes to reservations for the Chesapeake Bay Sailing Experience require seven (7) days advance notice.

Xperience Certificates® cannot be exchanged once a reservation for the experience has been made.

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