Eastern Shore of Maryland

Tour Description

Maryland’s Eastern Shore offers a peaceful landscape shaped by the Chesapeake Bay, maritime traditions, agriculture, and generations of remarkable people. Our private journeys explore charming waterfront communities, historic towns, natural landscapes, and the region’s rich African American heritage while revealing the enduring relationship between land and water.

Whether your interests include history, nature, photography, seafood, birding, maritime culture, or the Chesapeake Bay, each itinerary is thoughtfully tailored to your interests and paced for a relaxed and memorable experience.

Extend Your Journey

Many guests choose to combine the Eastern Shore with Annapolis to create one of our signature regional experiences. Depending on your interests and available time, this may be enjoyed as an extended 11–13 hour Grand Regional Journey or as a relaxed overnight itinerary that allows additional time to explore both regions.