Get ready because, gasp, we’re going to talk a little bit about boats with sails this month. And here’s why: even if you are a diehard powerboater, it can be an amazing experience to ply the waters of the Chesapeake aboard a classic skipjack or other historic vessel and gain a new perspective regarding the history and ecology of the Bay.

educational cruises
The skipjack Wilma Lee is docked at the Annapolis Maritime Museum.

And if you had any lingering doubts about sails gracing these pages, many of the ones we’ve included are skipjacks and thus watermen’s boats. They are the last working boats under sail in the United States, and in winter are used to dredge oysters from the floor of the Chesapeake Bay. While thousands used to work the Bay, today very few remain. Below are a few opportunities to experience these beautiful and historic vessels first-hand, along with some historic powerboat offerings as well.

Annapolis Maritime Museum

The Annapolis Maritime Museum offers public cruises, private charters, and educational programs aboard the historic skipjack Wilma Lee. One of only a few remaining Chesapeake Bay skipjacks, the Wilma Lee was built in Wingate, MD, in 1940 by the well-known boat builder Bronza Parks. 

Several public cruises are offered, including a heritage tour, sunset cruise, Wednesday night races, or specialty cruises. Certain offerings are only for ages 21 and up, so be sure to check the schedule at

The Wilma Lee education program turns the skipjack into a floating classroom where students can dredge for oysters and experience what life was like living on the water in the 1800s. Students will be actively engaged in STEM concepts, all while enjoying the beautiful Chesapeake Bay setting. 

The Calvert Marine Museum (CMM)

CMM in Solomons, MD, is home to a fleet of historic vessels including the Dee of St. Mary’s skipjack (one of the very few skipjacks ever built on the Western Shore, and one of only a handful of surviving skipjacks certified to carry passengers), the vintage sailing yacht Witchcraft (built in 1903), and the Wm. B. Tennison, a nine-log sailing bugeye built in 1899 and converted into a powered buyboat in 1908/1909.

educational cruises
The Calvert Marine Museum's Wm. B. Tennison. Photo by Bob Hall, courtesy of CMM

One-hour sightseeing cruises are available aboard the Tennison, taking guests past the busy Solomons inner harbor, Solomons Island and the Chesapeake Biological Laboratory, passing underneath the Governor Thomas Johnson Bridge, and turning back at Pt. Patience and the Naval Recreation Center. Departures are from the Calvert Marine Museum dock. Tickets cost $9 for adults and $5 for children (infants through age 12 years). 

In May and June, cruises run Wednesday through Sunday (and holidays) at 2 p.m. and 3:10 p.m. (if the 2 p.m. cruise is full, tickets will go on sale for a 3:10 p.m. cruise and there is a minimum of eight passengers). On Saturday, May 4, guests can enjoy free half hour cruises during the Solomons Maritime Festival.

For more details on any of the cruises available at CMM, visit

Chesapeake Bay Maritime Museum (CBMM)

When visiting CBMM in St. Michaels, MD, guests can opt to take a 70-minute narrated historic cruise of the Miles River aboard Patriot, a two-level 149 passenger cruise boat. The main deck is fully heated and air conditioned and the top deck is partially covered by a canopy/partially open to the sky. Tickets purchased online cost $27.50 for adults, with various other ticket options for seniors and children. Learn more and purchase tickets at

educational cruises
Scenic cruises aboard Patriot depart from CBMM's campus. Photo by Tom McCall/CBMM 

Private charters are also available on the museum’s historic floating fleet vessels including: the Winnie Estelle buyboat built in 1920 (she is currently undergoing routine maintenance and is temporarily unavailable), Rosie Parks (a skipjack built in 1955 by Bronza Parks), Edna E. Lockwood (built in 1189, the last of the historic sailing log-bottom bugeyes), and Old Point (a crab dredger constructed in 1909 from seven pine logs pinned together and hewn to shape). To learn more about private charters, visit Occasionally some of these vessels are available for cruises during special events at the museum, such as the annual Antique and Classic Boat Festival in June. 

educational cruises
Old Point, part of CBMM's floating fleet, is a crab dredger built in 1909. Photo courtesy of CBMM

S.S. John W. Brown

Experience World War II afloat aboard the S.S. John W. Brown, one of only two remaining, fully operational Liberty Ships that participated in World War II. While the Brown is available for dockside tours throughout the year, the Living History Cruise is a way to truly experience what life was like on the ship.

Each six-hour day cruise features music of the 1940s, period entertainment, historical re-enactments, and even fly-bys (weather permitting) of vintage World War II aircraft, while the ship’s Armed Guard gunners man the guns to defend the ship. Guests can also tour museum spaces, crew quarters, the bridge, and much more, including the 140-ton triple-expansion steam engine as it powers the ship through the water. Lunch, afternoon snacks, and beverages are included. 

educational cruises
Spend an exciting day in 1944 as you experience a sea and air adventure aboard the restored Liberty ship S.S. John W. Brown.

The next Living History Cruise is scheduled for Saturday, May 4. The deadline for ticket purchases is two weeks prior to the cruise, but you’ll want to reserve your spot early as these events often sell out. Tickets cost $250 per person. Learn more at

Sultana Education Foundation

The 1768 schooner Sultana is a modern full-scale reproduction of a 97-foot topsail schooner that patrolled the mid-Atlantic enforcing the hated “Tea Taxes” for Britain’s Royal Navy in the years preceding the American Revolution.

The Sultana Education Foundation (SEF) provides hands-on educational opportunities that promote stewardship of the Chesapeake Bay’s historic, cultural, and environmental resources. By helping students of all ages develop an appreciation for the Chesapeake Bay, Sultana is working to create a community of individuals who are dedicated to preserving this irreplaceable treasure.

educational cruises
Sultana under sail in the Chester River. Photo by Chris Cerino 

On school trips, students work with SEF’s professional staff to trawl for fish and crabs, conduct tests to monitor water quality, and learn about maritime life in the 18th century. SEF also offers two-hour public sails on the Sultana. Passengers are encouraged to help raise the sails, steer using Sultana’s seven-foot tiller, and explore the authentically reproduced crew’s quarters below-decks. Crew may even fire the swivel guns! Unless otherwise noted, all sails depart and return to the Chestertown Marina, 207 S. Water Street, in Chestertown, MD. For a schedule and ticket information, visit