Raise a sail. Raise a glass. Raise a heap of fresh oysters from the floor of the Chesapeake Bay.

Venture on board an authentic Chesapeake skipjack and you can learn to work like a waterman — or not. The choice is yours. Either way, you’ll have an unforgettable encounter with the Chesapeake’s nautical heritage.

The skipjack is unique to the Chesapeake Bay and first became a notable presence in the late 1800s. Designed specifically for dredging oysters, Chesapeake boat builders produced as many as 600 skipjacks in the years before World War I alone.

Then, as water pollution, disease and harvesting took their toll on Bay resources, watermen began leaving the Bay and many skipjacks went with them. As skipjacks declined, their status as a romanticized Bay icon grew.

About 27 skipjacks are in the water today, and many are no longer workboats. A few, like the Chesapeake Bay Foundation’s Stanley Norman, are dedicated to student education programs.

But a handful of skipjacks have become Bay ambassadors for the general public, with fun and relaxing cruises that provide a glimpse of the Bay’s past and motivation to protect its fragile future.

Skipjacks are broad wooden boats ranging from 40 to 60 feet in length, with most of the surviving skipjacks coming in at about 45 feet.

Skipjacks needed enough strength and power to pull an oyster dredge across the bottom of the Bay, even when the dredge is filled with oysters. As a result, they are rigged with an unusually large mainsail attached to a very long boom and paired with a smaller triangular foresail called a jib.

“That’s crucial on a light air day,” said Pete Lesher, chief curator of the Chesapeake Bay Maritime Museum. “Only the biggest boats would have the power to move the dredges across the oyster grounds, and that’s why the main is a very large sail.”

The weight of the rig might look odd to someone sailing for speed, but Lesher said it was designed with oystering in mind.

“If you are a sailboat racer, you’d say it would be better to have a taller rig with a shorter boom. That’s true if your object is to be windward,” Lesher said. “But watermen typically work an oyster bar with the wind at their side, going back and forth across an oyster bar, never beating to windward.”

While the rigging is distinct, a skipjack is also defined by what’s underwater: the shape of its hull. A skipjack has a “V-bottom,” which creates a hard angle between the side of the boat and its bottom, as opposed to a more rounded, egg-shaped hull.

“That made the boat easier to build and cheaper to build,” Lesher said.

The V-bottom also gives a skipjack stability. Combined with a broad deck, the design provided a good working surface for hauling in dredges and managing the piles of oysters that accumulated on deck.

Skipjacks were a major investment during their heyday, and many were owned in shares. A captain might only own a third of the boat under his command, or none at all.

Profits from the harvest were shared, too. In good years, a skipjack team typically included a captain and six crew — three men to work a dredge on each side of the boat. Once the harvest was sold, one-third of the profits went to the boat owners, one-third to the captain, and the remainder divided among the crew.

The name “skipjack” is a bit of mystery, and Lesher said the press might be partly to blame. “Skipjack” is a nickname for a fish in the Long Island Sound, and the term was used for other boats at Long Island and elsewhere on the Eastern seaboard.

“In 1889, a Baltimore Sun article talks about these new boats in the oyster fishery and calls them skipjacks. It seems like the term may have been misused in the press and it caught on,” Lesher said.

Some would say the proper name for a skipjack is a two-sailed bateau, especially on the lower Eastern Shore. “Before 1960, they would more than likely have corrected you,” Lesher said.

Skipjacks held on in Maryland longer than Virginia because Maryland did not allow dredging with motor-driven vessels.

“Today’s skipjack owners, those that still work as watermen, will tell you that the use of these boats in modern American fisheries is completely anachronistic,” Lesher said. “They are working a fishery of the past and they are conscious of that. Why do they do it? They love it. There are easier ways to make a living. But these boats do have a certain allure to them.”

Some skipjacks offering public cruises are also used to dredge oysters for commercial sale if time allows and the harvest is relatively good.

If you sail on skipjacks like the Rebecca T. Ruark, Herman M. Krentz, or the Dee of St. Mary’s, you’ll not only take in the Bay’s dramatic scenery but keep company with captains who have years of experience both working the Bay and teaching their passengers about its ecosystem.

Most public cruises last about two hours, and children are welcome. Dredging demonstrations are common, and you can observe the process or jump in to help. For a special adventure, join the Martha Lewis this November for an immersive experience as “waterman for a day.”

This trip books fast, so call soon to reserve your spot.

But you don’t have to work like a waterman to experience a Chesapeake skipjack. Lots of skipjack cruises are quite leisurely, and you can often bring your own picnic aboard.

The Martha Lewis also offers a wide range of themed tours with wine, history, “treasure” hunts for kids, and “Martinis and Moonlight.” This August, the night skies will be treated with the unusual occurrence of not one but two full moons. “The second one is called a ‘blue moon,’ so we are going out on that day and offering Blue Moon beer,” said Cindi Beane, director of the Chesapeake Heritage Conservancy, which owns the boat.

If your curiosity is roused but you are a die-hard landlubber, stop by the Chesapeake Bay Maritime Museum in St. Michaels, MD. On the grounds, you’ll find the skipjack Rosie Parks. Built in 1955, the Rosie is being rescued and restored by a team of volunteers and descendants of the boat’s builder, Bronza Parks, with aims to send her afloat in October 2013.

“When it’s finished, it should look like Bronza’s hands built it,” said communications director Tracey Munson. “It’s a piece of Chesapeake history, unfolding right here.”

Skipjack excursions offer a variety of experiences

Along with public sails for individuals and families, skipjacks also offer private charters for birthday parties, corporate events, fishing trips and special occasions. Most have programs for school groups. Advance tickets may be recommended or required; call for details.

Rebecca T. Ruark (1886):
Sails daily from Tilghman Island with nautical tales and ecology lessons from fifth-generation waterman Capt. Wade Murphy. Fee: $15–$30. www.skipjack.org, 410-886-2176.

Herman M. Krentz (1955):
Sails from the Chesapeake Bay Maritime Museum in St. Michaels, MD, April through October, captained by waterman and environmental educator Ed Farley. Fee: $18–$35. 410-745-6080, www.oystercatcher.com or hmkrentz@bluecrab.org.

Dee of St. Marys (1979):
Sails from St. George Island in Southern Maryland under waterman and environmental educator Capt. Jack Russell. Note: The Dee is on shore for restoration and may not be available until later in the season. www.skipjacktours.com, 301-994-2245, info@thebaylab.org.

Martha Lewis (1955):
Sails from Havre de Grace, June to mid-October, with weekend public cruises. Themed cruises with wine, treasure hunts, lighthouses and moonlight require reservations. “Waterman for a Day,” is offered in the fall. Fee: $10–$20. www.skipjackmarthalewis.org, 410-939-4078 or director@chesapeake-heritage.org.

Nathan of Dorchester (1994):
The youngest and possibly last skipjack built for oyster dredging sails on the Choptank River from Cambridge, MD, from late April through early November. Public sails and dredging experiences on weekends. Fee: $7–$30. 410-228-7141
www.skipjack-nathan.org, or info@skipjack-nathan.org.

Claud M. Somers (1911):
Sails from the Reedville Fishermen’s Museum on Virginia’s Northern Neck, with public sails two Saturdays per month starting on June 16. Fee: $25; reservations required.
www.rfmuseum.org, 804-453-6529 or office@rfmuseum.org.

At the Races

53rd Annual Skipjack Races & Festival:
Sept. 1–3, Deal Island, MD. Parade, car show, music, arts and crafts 4–10 p.m. Sept. 1; 1–11:30 p.m. Sept. 2 & 8 a.m.-6:30 p.m. Sept. 3. Blessing of the fleet & skipjack race: 8 a.m. Sept. 3.

16th Annual Choptank Heritage Skipjack Race & Arts Festival:
Sept. 22–23, Cambridge, MD. Skipjack race begins at 10 a.m. Sept. 22. Arts festival features free sails on the Nathan of Dorchester.