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Chesapeake to Winston-Salem

Compare connected destinations, explore road, rail, and bus options, estimate costs, and build a better route.

The two cities

Chesapeake

Virginia, United States

Overall
6.3
Connector
6.5
Per day (mid-range)
$185

Beaches

  • Drive
  • Bus
  • Airport

Peak: Summer

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Winston-Salem

North Carolina, United States

Overall
6.1
Connector
8.8
Per day (mid-range)
$175

Car-free travelHistoryWine country

  • Drive
  • Train
  • Bus
  • Airport

Peak: Periods include the National Black Thea…

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Compare in detail

Winston-Salem → Chesapeake Route Circle

For people considering or completing the trip between Winston-Salem and Chesapeake: how long to stay, how to get there, and what to add or skip.

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