This unique exploration of the waterways around the Chesapeake Bay offers an intriguing portrait of American history, architecture, and culture from the Colonial era to the present. Departing from Philadelphia, we venture through the Chesapeake and Delaware Canal to arrive at Annapolis, where we learn about its naval heritage and discover its many historic sites. Our visits include St. Michaels, home to some of the world’s best seafood, Tangier Island, an isolated fishing community whose inhabitants speak an English Restoration–era dialect, and history-steeped Richmond, where we visit Revolutionary and Civil War sites and discover George Washington’s stately home at Mount Vernon. Stepping back further in history, we pay a visit to Colonial Williamsburg, America’s premier living museum. Our journey concludes in historic Alexandria, where an optional extension explores our nation’s capital. During the bright, crisp days of fall, we enjoy a memorable survey of some of America’s most historic maritime towns and waterways.

Itinerary at a Glance

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Days 1-3
Philadelphia, Pennsylvania / Annapolis, Maryland / St. Michaels

After arriving in Philadelphia, we cruise to through the Chesapeake and Delaware Canal to Annapolis, a city of narrow brick streets, colonial mansions, and home to the historic U.S. Naval Academy. In St. Michaels, a quaint waterfront village set on a picturesque peninsula, we explore the town with its manicured colonial, federal and Victorian homes, art galleries, and interesting maritime history.

Days 4-5
Tangier Island, Virginia / Richmond / Petersburg

We call at Tangier Island, whose relative isolation creates a pleasant sense of tranquility. European colonists, including John Smith, settled on the island in the 17th century, and during the War of 1812 the British used it as a staging area. We travel to Virginia’s historical capital of Richmond, which is filled with many interesting Revolutionary and Civil War sites and museums. In the afternoon we travel south for an excursion to Petersburg, an important city for the Confederacy during the Civil War, and visit its battleground sites.

Days 6-8
Colonial Williamsburg / Mount Vernon / Alexandria

The capital of the Virginia colony from 1699 to 1780, Williamsburg is the nation’s premier living museum, offering us a glimpse of life as it was in the 17th and 18th centuries. After a guided tour, we enjoy time at leisure to explore the museums and side streets filled with taverns, bakeries, and the restored houses of wheelwrights, coopers, apothecaries, and other tradesmen. Sailing up the Potomac River, we reach Mount Vernon, George Washington’s massive estate and gardens. We explore the sweeping grounds including the mansion, museum, slaves’ quarters, and the gardens. Disembark in Alexandria on Day 8 and fly home.

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What the Trip is Like

The trip is rated Level 1, Easiest. There are shore excursions featuring walks, and it is appropriate for anyone in good health who is physically active.

Explanation of Trip Levels