Chesapeake Bay Cruises from the Eastern Shore

There are many opportunities for Chesapeake Bay cruises from the small ports of the Eastern Shore. The Shore is defined by its location on the edge of the Bay, and it is natural for any visitor to want to get out on the water. Options for your cruise on the Bay include tall sailing ships and passenger ferries to Tangier Island or Smith Island.

Some cruises are seasonal; operating only in the warm weather months. See our list below for more information. Enjoy your Eastern Shore Chesapeake Bay cruise adventure!

Two small ship cruise lines offer Chesapeake Bay cruises from Baltimore. These aren't day cruises, they're week-long explorations of the historic and beautiful ports on the Bay and the rivers that pour into it. The Chesapeake Bay is one of America's great waterways and is well worth a cruise vacation.

Tallship Cruises on the Chesapeake Bay

The schooner Sultana, a reproduction of a 1768 schooner, is the schoolship of the Chesapeake. It offers 2-hour public sails and daysails on a limited schedule. Most of the Sultana's sailings are from Chestertown, Maryland. Advance reservations are highly recommended.

The schooner Serenity offers sunset sails and day charters departing from the town of Cape Charles, Virginia. Lend a hand setting sail or relax with your favorite beverage.

Skipjack Cruises

The skipjack Rebecca T. Ruark is the oldest working skipjack on the Chesapeake Bay. 2-hour cruises, 7-days a week from Tilghman, Maryland.

The skipjack Nathan of Dorchester offers cruises on the scenic Choptank River, help raise her sails or take a turn at the helm, and hear stories of the working watermen. Cambridge, Maryland.

Smith Island Ferry

Take a Smith Island cruise from Crisfield, Maryland across the Tangier Sound or the Chesapeake Bay to Smith Island. Enjoy a self-guided walking tour of the island, or rent a golf cart or a bicycle. There are gift shops, a Blackwater National Wildlife Refuge Visitor Center, and the Smith Island Center to see.

Tangier Island Ferries

The Capt. Eulice is a passenger ferry that cruises from Onancock, Virginia to Tangier Island. The ferry operates from May to mid-October, Tuesday to Sunday. The trip takes about an hour and a half in each direction. Tangier Island is a small island in the center of the Chesapeake Bay. It has a few hundred quaint inhabitants and no cars.

The Steven Thomas ferry cruises from Crisfield, Maryland to Tangier Island. It also operates from May to October. The Steven Thomas is a 300-passenger ship with an air-conditioned cabin, sun deck and restrooms.

Eastern Shore Real Estate

Chesapeake Bay Cruises
from the Eastern Shore

Eastern Shore Hotels
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Eastern Shore Events
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Eastern Shore Towns