Your Itinerary

1Embark in Baltimore, MD
From the cobblestone streets to the colonial architecture and Fort McHenry – the history of Baltimore is the history of America.

2Williamsburg & Yorktown, VA
No three towns represent early American history better than Yorktown, Colonial Williamsburg, and the Jamestown Settlement. You can take the Yorktown Trolley through 9 stops throughout historic Yorktown, including battlefields and the Watermens Museum. Transportation is available to 18th century Colonial Williamsburg, once the largest British capital in the New World. From there, you can take a shuttle to the Jamestown Settlement, the first permanent English colony established in 1607. If you’d like to spend your day a little differently, head over to the Williamsburg Winery, the largest winery in Virginia.

3Crisfield, MD & Tangier, VA
Crisfield is the ‘Blue Crab Capital of the World’! Enjoy a walking tour of the port, with a visit to the Tawes Historical Museum where you can learn about the crabbing history of the port – from the early colonists learning from the Native Americans, to the evolution of modern crab and oyster processing. Just a ferry away is Tangier Island, setting in 1608 by Captain John Smith and now a village built by the crabbing industry and the watermen who work the Bay.

4Cambridge, MD & Oxford, MD
See the Bay aboard the skipjack Nathan! Skipjacks are oyster dredging sailboats, used in the Chesapeake Bay since the 1880s. Join the crew of the Nathan as you sail the Choptank River. If you’d rather relax, head towards the 18th century LaGrange Plantation for a Sweet Tea party! Oxford was founded 1683, and quickly set up as the only port of entry for British trade on the East coast. The town flourished until the Revolutionary War, and is now a quiet town that you can explore by walking tour. Or you can choose to visit the Oxford Museum or Oxford Custom House – a replica of the first Federal Custom House.

5St. Michaels, MD
Start with a walking tour of colonial St. Michaels before venturing out to explore the many options in this town. St. Michaels is home to the Chesapeake Bay Maritime Museum, and 18-acre waterfront property with 10 exhibit buildings, working boatyard and the historic lighthouse. Or take a private eco tour of the Chesapeake Bay with a naturalist to point our wildlife and landmarks as you go.

6Annapolis, MD
A trolley tour of Annapolis is available, giving you a good overview of the history and the town. Get your ID out for a tour of the Naval Academy, founded in 1845. Or if those don’t interest you, perhaps visit the Annapolis Maritime Museum, located in an old oyster packing building, or take an audio tour of historic Annapolis.

7Disembark in Baltimore, MD
Disembark after breakfast.