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Chesapeake Bay trip planner
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Chesapeake Bay
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Places to visit in Chesapeake Bay
Colonial BeachTrip planner
Best for: Monument, State Park, Pier / Boardwalk
IrvingtonTrip planner
Best for: Winery / Vineyard, Religious Site, History Museum
GloucesterTrip planner
Best for: Historic Site, Gift & Specialty Shop, Hiking Trail
KilmarnockTrip planner
Best for: Winery / Vineyard, Gift & Specialty Shop
ReedvilleTrip planner
Best for: Specialty Museum, Wildlife Area
Historic Sites in Chesapeake Bay
Hidden gems in Chesapeake Bay
Museums in Chesapeake Bay
Trails in Chesapeake Bay
Wineries in Chesapeake Bay
Where to stay in Chesapeake Bay

Browse hotels, guesthouses, and unique homes and book your stay on the world's leading accommodation sites.
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Recently planned trips to Chesapeake Bay
10 days in United States
BY A USER FROM UNITED STATES
Philadelphia
Lancaster
Hershey
2 days in United States
BY A USER FROM UNITED KINGDOM
Richmond
West Point
Manteo
5 days in Chesapeake Bay
BY A USER FROM UNITED STATES
Colonial Beach
Irvington
15 days in East Coast of USA, New Orleans & Mobile
BY A USER FROM UNITED KINGDOM
Boston
Salem
Niagara Falls
21 days in United States
BY A USER FROM SAUDI ARABIA
Miami
Orlando
Amelia Island
12 days in Chincoteague Island, Virginia Beach & Tappahannock
BY A USER FROM UNITED STATES
Chincoteague Island
Virginia Beach
Tappahannock
1 day in Tappahannock
BY A USER FROM UNITED STATES
General's Ridge Vineyard and Winery
1 day in Gloucester
BY A USER FROM UNITED STATES
Rosewell Ruins
Whitley's Peanut Factory
Beaverdam Park
14 days in Chesapeake Bay
BY A USER FROM UNITED STATES
Colonial Beach
Gloucester
Reedville
8 days in Chesapeake Bay
BY A USER FROM UNITED STATES
Reedville
Gloucester
Colonial Beach
5 days in Warsaw
BY A USER FROM GERMANY
Menokin
Point Lookout State Park
Piney Point Lighthouse Museum & Historic Park
1 day in Irvington
BY A USER FROM UNITED STATES
Belle Isle State Park
Historic Christ Church
The Dog and Oyster Vineyard Micro-Vineyard and Oyster Bar