Maryland

19 Sep 2024

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Chesapeake Bay Road Trip Itinerary

Chesapeake Bay Road Trip Itinerary Overview

Embark on a captivating journey around the Chesapeake Bay with this well-curated road trip itinerary. Your adventure begins in Annapolis, MD, known for its historic charm, waterfront ambiance, and the prestigious United States Naval Academy. Dive into the rich maritime heritage at the Chesapeake Bay Maritime Museum in St. Michaels, where you'll explore exhibits and historic boats offering insights into the area's nautical past.

Next, nature enthusiasts will marvel at the Blackwater National Wildlife Refuge, a sanctuary brimming with diverse ecosystems and wildlife-watching opportunities. Continue your journey to Calvert Cliffs State Park, where the dramatic, fossil-studded cliffs along the bay, coupled with serene hiking trails, beckon fossil hunters and nature lovers alike.

Conclude your road trip at Point Lookout State Park, situated at the southernmost tip of Maryland. This historical site offers stunning bay views, a peek into Civil War history, and a variety of outdoor activities, including camping, fishing, and wildlife observation. Each stop on this itinerary promises a unique experience that beautifully captures the essence of the Chesapeake Bay region.

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1
Annapolis, MD
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Annapolis is known for its historic charm, vibrant waterfront, and as the sailing capital of the United States. The city offers delicious seafood, picturesque streets, and the United States Naval Academy.
2
Chesapeake Bay Maritime Museum, St. Michaels
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The Chesapeake Bay Maritime Museum in St. Michaels provides a fascinating glimpse into the rich maritime heritage of the Chesapeake Bay area, featuring exhibits, historic boats, and insightful tours.
3
Blackwater National Wildlife Refuge
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Blackwater National Wildlife Refuge is a haven for wildlife enthusiasts, offering opportunities for bird watching, hiking, and observing the diverse ecosystems of wetlands, forests, and open fields.
4
Calvert Cliffs State Park
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Calvert Cliffs State Park is renowned for its stunning fossil-laden cliffs along the Chesapeake Bay, scenic hiking trails, and a serene beach that offers excellent opportunities for fossil hunting and picnicking.
5
Point Lookout State Park
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Point Lookout State Park is a historic and scenic spot located at the southern tip of Maryland. It's known for its beautiful bay views, rich Civil War history, camping, fishing, and abundant wildlife.

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Stay Recommendations

Historic Inns of Annapolis
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4.6
Historic Inns of Annapolis
These charming inns offer a unique stay in the heart of Annapolis, combining modern comforts with historic elegance and character.
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4.6
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The Inn at Perry Cabin
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4.5
The Inn at Perry Cabin
Located in St. Michaels, this luxurious waterfront hotel offers a serene escape with stunning views, a spa, and fine dining.
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4.5
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Black Walnut Point Inn
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4.7
Black Walnut Point Inn
Situated on a secluded point at Tilghman Island, this quaint inn offers panoramic views of the Chesapeake Bay, making it ideal for a peaceful retreat.
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4.7
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Solomon's Victorian Inn
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4.9
Solomon's Victorian Inn
A unique bed and breakfast located in a beautifully restored Victorian house in Solomon's Island, close to Calvert Cliffs State Park.
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4.9
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Island Inn & Suites, Ascend Hotel Collection
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4
Island Inn & Suites, Ascend Hotel Collection
Located near Point Lookout State Park, this hotel offers rooms with private balconies overlooking St. George Island and exceptional sunset views.
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4