Full-Day Eastern Shore of Maryland Tour from Annapolis
Highlights
Columbia (Maryland)
photography, historical, sightseeing
Private Tour
1 Day
Easy
English
Description
Embark on a full-day tour of Maryland’s beautiful Eastern Shore, starting with a scenic drive across the Chesapeake Bay Bridge and a stop on Kent Island for breathtaking views. Explore the colonial streets of Chestertown, home to Washington College, before continuing to your choice of two charming destinations—Easton, Cambridge, Oxford, or St. Michaels. Stroll historic towns, learn about local heritage at cultural sites, and enjoy authentic Maryland seafood such as crabs and oysters.
Itinerary
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Full-Day Itinerary: Eastern Shore of Maryland
- Morning Pick-Up and Drive Across the Chesapeake Bay Bridge
Begin your day with a pick-up from your hotel or lodging in Annapolis or the surrounding area. Drive across the iconic Chesapeake Bay Bridge and enjoy panoramic views of the bay. Stop briefly on Kent Island for coffee, a snack, and a scenic photo opportunity of the bridge and waterfront. Visit Historic Chestertown
Continue the journey to Chestertown, one of Maryland’s most important colonial cities and home to Washington College. Walk through the historic streets, admire the preserved Georgian architecture, and soak in the charm of this waterfront town.Choose Two Destinations for the Afternoon
After exploring Chestertown, select two of the following destinations to tailor your Eastern Shore adventure:Historic Easton – Stroll through this vibrant town filled with galleries, shops, and historic landmarks.
Cambridge – Visit the Harriet Tubman Museum (currently under repair as of August 2025, but the surrounding town and history remain inspiring).
Oxford – Experience Maryland’s seafood culture by dining on fresh crabs or oysters in a picturesque setting by the water.
St. Michaels – Wander through this charming harbor town, explore boutique shops, and enjoy views of the Chesapeake Bay Maritime Museum and waterfront.
Scenic Drive Back
End the day with a comfortable drive back across the Chesapeake Bay Bridge, returning to your hotel or lodging in the evening with lasting memories of Maryland’s Eastern Shore.
- Morning Pick-Up and Drive Across the Chesapeake Bay Bridge
What's Included
What's Excluded
Know Before You Go
What To Bring
Cancellation Policy
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For cancellations upto 2 days before the tour -
Refund of 80% of the tour price.
Price
| The Group Size and Price | |
|---|---|
| 1 to 3 | /group |
| 4 to 7 | /group |
| 8 to 12 | /group |
| 13 to 20 | /group |
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This is a private tour |
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