Chesapeake Windsail Cruises Corporation founder and president Nathaniel Pope Jr. recently announced the company’s new cruise service that departs four times daily, Tuesday through Sunday, out of Chesapeake Beach Resort & Spa located in the bayside town of Chesapeake Beach.

Chesapeake Windsail Cruises (CWC) offers regularly scheduled 2 1/2-hour cruises for up to six people aboard the 42-foot limited edition sailing yacht, “Eternal Hope.” The company also provides moonlight cruises, private cruises and cruises for special occasions.

Pope, a long-time sailing enthusiast and Calvert County resident, said it was a visit in 2015 from friends of the family that sparked his idea for the business.

“I thought about if I had a boat, maybe I could take people out,” Pope said. “So I checked around to see what we had in the area and nobody in the Chesapeake Beach area had this service.”

“So I looked into it, started checking it out,” Pope added. “My whole thought moved away from me just owning a boat for pleasure, but of becoming a business. So then I started developing the model so that it was truly a business to the point where there are plans for us to expand to five other ports.”

In April of this year, Pope put his plans in action with the launch of Chesapeake Windsail Cruises Corporation that offers passengers their choice of a morning, afternoon or evening excursion across the scenic waters of the Chesapeake Bay.

“We like to say that we’re not just a guy with a boat. We have scheduled trips out,” Pope said. “You’re buying a seat on the boat. The scheduled times are 9 [a.m.], 12 [noon], 3 [p.m.] and then the 6 o’clock sunset cruise.”

“We have five Coast Guard-licensed captains. We have three first mates that all have excellent sailing skills,” he said.

Pope said CWC also offers a moonlight cruise from 9 to 10:30 p.m. on nights during the month that have a full moon; private cruises for outings with family, friends and co-workers; themed and special cruises complete with party favors and extra added touches to celebrate weddings, birthdays, anniversaries, or other special occasions; and a series of Fourth of July fireworks cruises to view local displays from the bay.

“Hands down, the best sailing experience I have ever had … they are very kind and very knowledgeable,” said Hannah Simone of Great Falls, Va., of her two cruise experiences aboard CWC’s “Eternal Hope” sailing yacht. “I encourage anybody who wants to relax and get a little spoiled to take one of their cruises.”

Pope said CWC also offers summer internships aboard the “Eternal Hope” for local high school and college students interested in the maritime industry.

Going forward, Pope said he plans to expand CWC’s cruise services to ports in Annapolis, Baltimore, National Harbor and Hampton, Va., and looks to offer a cruise that sails to St. Michaels on the Eastern Shore.

“Our mission is to provide our passengers with a safe experience and a very memorable experience,” Pope said. “And to a lot of people, an introduction to sailing.”

For more information on Chesapeake Windsail Cruises or to book a cruise, go to