Chesapeake Tours offers group tour adventures from the Chesapeake Bay to the Mid-Atlantic Beaches, and throughout the greater Washington D.C. metro area, Annapolis and Baltimore. Select one of our popular packaged themes or let us customize your itinerary to create an experience that will meet your group’s unique interests and needs.

Bus Tours

Experience the life of Harriet Tubman, and her gripping journeys on the Underground Railroad, along the 125 mile-long byway through Dorchester and Caroline Counties, Maryland. All tours include a visit to the Harriet Tubman Underground Railroad Visitors Center in Church Creek, MD. Our Harriet Tubman tours are the only tours designed and operated by Byway trained and NAI Certified Interpretive Guides.

From our famous Maryland steamed crabs and succulent oysters, to our bountiful fresh locally-grown produce, you will savor our traditional shore cooking through emerging menus of farm-to-table experiences. Follow our winery or brewery trails and enjoy hand-crafted beverages and unspoiled views. Explore the rapidly expanding destinations with an eye for good times, good food and good friends. Pair an authentic dining experience with any one of our rich heritage tours.

Uncover the roots of many cultures—Native American, Early Colonial Period, African-American, Maritime and Women’s history. Explore the region’s maritime and agricultural legacies. Costumed tours at historic homes, groundbreaking archaeological sites, bay boat restoration and wooden decoy carving are some of the experiences you will find on our specially tailored tours.

Walking Tours

Description coming soon!