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How to get fromWinchester to Florida Keysby bus, plane, bus (Flixbus, Greyhound), train, car, shuttle, or taxi

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There are 9 ways to get from Winchester to Florida Keys by bus, plane, bus (Flixbus, Greyhound), train, car, shuttle, or taxi

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.

  1. Bus to Washington Dulles International Airport, fly to Key West International Airport

    best
    1. Take the bus from Front Royal Walmart to Dulles International Airportbus bus
    2. Fly from Washington Dulles International Airport (IAD) to Key West International Airport (EYW)plane plane IAD - EYW
    8h 44m
    $217–546

  2. Bus

    1. Take the bus from Crooked Run Park & Ride to 14th St @ F St NWbus bus
    2. Take the bus from Washington Union Station to Ft Lauderdale Broward Park & Ridebus bus
    3. Take the bus from Ft Lauderdale Broward Park & Ride to Miami Airport Stationbus bus
    4. Take the bus from Miami Airport Station to Big Pine Keybus bus
    32h 15m
    $251–406

  3. Train, bus

    1. Take the train from Martinsburg Amtrak Station to Hollywood Amtrak Stationtrain train Floridian
    2. Take the bus from Miami Airport Station to Big Pine Keybus bus Greyhound US0720s
    38h 24m
    $499–1,015

  4. Drive 1,199.3 mi

    1. Drive from Winchester to Florida Keyscar car 1,199.3 mi
    21h 28m
    $219–317

  5. Bus to Ronald Reagan Washington National Airport, fly to Key West International Airport

    1. Take the bus from Crooked Run Park & Ride to Virginia Ave @ 21st St NWbus bus
    2. Fly from Ronald Reagan Washington National Airport (DCA) to Key West International Airport (EYW)plane plane DCA - EYW
    9h 22m
    $262–809

  6. Bus to Ronald Reagan Washington National Airport, fly to Miami International Airport, shuttle

    1. Take the bus from Crooked Run Park & Ride to Virginia Ave @ 21st St NWbus bus
    2. Fly from Ronald Reagan Washington National Airport (DCA) to Miami International Airport (MIA)plane plane DCA - MIA
    3. Take a shuttle bus from Miami, FL - International Airport to Big Pine Key, FLshuttle bus
    11h 23m
    $347–1,249

  7. Bus to Washington Dulles International Airport, fly to Fort Lauderdale–Hollywood International Airport, shuttle

    1. Take the bus from Front Royal Walmart to Dulles International Airportbus bus
    2. Fly from Washington Dulles International Airport (IAD) to Fort Lauderdale–Hollywood International Airport (FLL)plane plane IAD - FLL
    3. Take a shuttle bus from Fort Lauderdale, FL - International Airport to Big Pine Key, FLshuttle bus
    11h 13m
    $352–696

  8. Bus to Washington Dulles International Airport, fly to Miami International Airport, shuttle

    1. Take the bus from Front Royal Walmart to Dulles International Airportbus bus
    2. Fly from Washington Dulles International Airport (IAD) to Miami International Airport (MIA)plane plane IAD - MIA
    3. Take a shuttle bus from Miami, FL - International Airport to Big Pine Key, FLshuttle bus
    10h 55m
    $342–626

  9. Taxi, train, train to Baltimore-Washington International Airport, fly to Miami International Airport, shuttle

    1. Take the taxi from Winchester to DUFFIELDS W VA MARC ebtaxi taxi
    2. Take the train from DUFFIELDS W VA MARC eb to Washington Union Stationtrain train
    3. Take the train from Washington Union Station to BWI Thurgood Marshalltrain train
    4. Fly from Baltimore-Washington International Airport (BWI) to Miami International Airport (MIA)plane plane BWI - MIA
    5. Take a shuttle bus from Miami, FL - International Airport to Big Pine Key, FLshuttle bus
    12h 29m
    $283–1,246

Washington Dulles International Airport (IAD) to Key West International Airport (EYW) flights

Calendar41Weekly Planes
Duration4h 59mAverage Duration
Ticket$80Cheapest Price
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Questions & Answers

Map of how to get from Winchester to Florida Keys.ExpandLaunch map view
  • Distance: 1,122.7 mi
  • Duration: 8h 44m

What companies run services between Winchester, VA, USA and Florida Keys, FL, USA?

You can take a vehicle from Winchester to Florida Keys via Crooked Run Park & Ride, 14th St @ F St NW, 13 St NW+F St NW, Massachusetts Av NE+1 St NE, Washington Union Station, Ft Lauderdale Broward Park & Ride, Miami Airport Station, Big Pine Key, Big Pine Key - CVS / MM30, and Sugarloaf Key - Lower - Sugarloaf Lodge in around 32h 15m.

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