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Key West to Chesapeake buses

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Trip Overview

The bus between Key West and Chesapeake takes 2d 2h. The bus runs, on average, 3 times per week from Key West to Chesapeake. The journey time may be longer on weekends and holidays; use the search form on this page to search for a specific travel date.

2d 2h
Duration
1,252 mi
Distance
$241
Average price
3 times a week
Frequency

Key West to Chesapeake bus times

Buses run 3 times a week between Key West and Chesapeake. The service departs Key West at 4:15 PM in the afternoon, which arrives into Chesapeake at 19:14:00. All services require a transfer at Big Pine Key - Auto Store / NAPA MM30 and take an average of 2d 2h. The schedules shown below are for the next available departures.

Departing Thursday, November 12, 2026

  •  → 

    Arrives +2 days

    Key West TransitGreyhound USAFlixbus USAFlixbus USAHampton Roads Transit (HRT)2d 2h • 4 changes

Departing Saturday, November 14, 2026

  •  → 

    Arrives +2 days

    Key West TransitGreyhound USAFlixbus USAFlixbus USAHampton Roads Transit (HRT)2d 2h • 4 changes

Departing Sunday, November 15, 2026

  •  → 

    Arrives +2 days

    Key West TransitGreyhound USAFlixbus USAFlixbus USAHampton Roads Transit (HRT)2d 2h • 4 changes

Frequently asked questions

Want to know about travelling from Key West to Chesapeake? We have put together a list of the most frequently asked questions from our users such as: What is the cheapest mode of transport? What is the quickest option? How much do tickets usually cost? and many more.

Map of how to get from Key West to Chesapeake.ExpandLaunch map view
  • Distance: 1,252.4 mi
  • Duration: 2d 2h

What companies run services between Key West, FL, USA and Chesapeake, City of Chesapeake, VA, USA?

You can take a bus from N Roosevelt & 3rd Street to Robert Hall & Military via Big Pine Key - Auto Store / NAPA MM30, Big Pine Key, Miami Airport Station, Richmond, Richmond, Norfolk, and Military & Poplar Hall in around 30h 1m.

Operators