45 F
Sunday, February 5, 2023
HomeOutdoorsBoatingFun Days on the Bay—Getting out on the Chesapeake

Fun Days on the Bay—Getting out on the Chesapeake


Cool Bay breezes, workboats grinding by, the prickle of sun and the freedom of a day on the open water—there is no better way to spend a sultry summer day in Maryland than cruising on the Chesapeake.

But boat ownership isn’t a prerequisite to beating the heat on the Bay. Maryland’s waterfront towns and cities boast plenty of family-friendly watercraft perfect for a day-long cruise or a three-hour tour. Whether it’s a tall ship, a skipjack, or a packet boat, you can take your family out on the water to learn about the Bay’s history, ecology, or just enjoy a relaxing sunset cruise on the Chesapeake. Check out these six tour boats for a wide variety of fun trips on the Bay.

Schooner Woodwind19553950 10155420558542433 1855922199857457150 n
Welcome to the “Sailing Capital of the United States!” Whether its aboard Woodwind or Woodwind II, these classic 74-foot schooners provide a wonderful way to introduce your family to the joys of sailing out of Annapolis harbor. Elegant and comfortable, with friendly, capable captains and crew well-seasoned in family on-the-water experiences, Woodwind’s two-hour public cruises are perfect for families with children over five. Little ones will love seeing the Bay Bridge (and maybe even sailing underneath), spotting the iconic Thomas Point Lighthouse, and getting hands-on with a turn at the wheel. With up to four cruises a day, it’s easy to fit in a sail on the Woodwind during a day or afternoon visit to Annapolis.

River Packet
A sunset cruise on Chestertown’s 65-foot classic touring yacht, River Packet, is like a trip back to the Bay’s great steamboat era, when travelers enjoyed excellent food, drinks, and comfort along with stunning river views. The lower cabin is climate controlled with a small bar and catered eats for cruisers, while the expansive upper deck provides ample seating and great views of the Chestertown waterfront, watermen’s poundnets, and the Chester River bridge. Cruises run on Thursday, Friday and Saturday nights. For families with an eye toward an earlier bedtime, a Saturday afternoon tour or Sunday brunch cruise might be just the ticket. All children’s admission 12 and under is discounted.

schoonersultanaSchooner Sultana
Travel back in time to Chestertown’s heyday as a colonial port on the schooner Sultana, a replica of a 1768 British vessel used to enforce the tea taxes. Used primarily as an educational vessel by the Sultana Education Foundation, Sultana’s 2-hour public sails are a great way for families with children over five to enjoy an on-the-water experience that recalls the Golden Age of sail. Participants can enjoy a peek at the crew quarters below decks (also built to 18th century specifications), watch the crew climb the rigging, and maybe get a chance to haul the sails or take a turn at the helm. Kids will also get a kick out of Sultana’s small cannon, which is fired once a cruise to the delight—and surprise—of everyone on board.

St. Michaels 
As part of a day or weekend getaway to St. Michaels, a narrated cruise aboard the Patriot is a wonderful way to enjoy the gorgeous harbor and Miles River views with the entire family. With a climate-controlled interior, a full snack bar, restroom facilities and stroller access, the Patriot provides a full complement of amenities that parents will appreciate. 

The Patriot is also dog-friendly, so plan to bring the family pooch. The vessel’s two-story design with top deck and promenade as well as ample outdoor seating gives cruise-goers a front-row seat for the lovely river scenery. Kids will have fun osprey-spotting at the nest on the channel marker as the Patriot leaves St. Michaels harbor on the 65- to 75-minute outing.

Winnie EstelleWinnieEstelle
St. Michaels
The Chesapeake Bay Maritime Museum is fantastic destination for families, with its working boatshop, Bay-themed exhibits and Hooper Strait Lighthouse. The fun continues onboard the museum’s historic buyboat, Winnie Estelle, which takes visitors of all ages out on the Miles River. Once part of the Bay’s fleet of middlemen that bought oysters and fish from watermen and hauled them to Chesapeake cities for processing, authentic buyboats are scarce today—making a Winnie Estelle cruise extra special. On this 45-minute cruise, families will hear stories about watermen and workboats, spot rays, eagles, osprey and sometimes even dolphins, and take a turn at the wheel. Themed ecology cruises for families with hands-on science activities are also available on select dates.


NathanofDorchester 1630x860Skipjack Nathan of Dorchester
Run by an independent nonprofit, the skipjack Nathan of Dorchester departs from the heart of the Cambridge waterfront on Saturday afternoons in the spring, summer and fall for 2-hour public sails. Built in 1994 as an educational vessel telling the story about the Bay’s unique oyster sailing fleet, the public cruises help get little ones into the skipjack action with a real oyster dredging demonstration. 

Kiddos can check out all the little crabs, mussels, barnacles, fish and oysters hauled in the dredge—and hold them if they’re feeling brave—while learning about the Bay’s amazing oyster history and ecology from the onboard docents. Parents will enjoy the Choptank River’s stunning scenery, the sailboats, workboats, and the option to BYOB onboard.


For more Chesapeake Bay fun, check out our Boating page, which has ideas for kayak and canoe outings, fishing trips and more!

- Advertisement -
- Advertisement -

Tips From our Sponsors

Stay Connected


Most Read