Rome2Rio

How to get fromWinchester to Key Westby bus, plane, bus (Flixbus, Greyhound), train, car, or taxi

Find Transport to Key West

See all options

There are 6 ways to get from Winchester to Key West by bus, plane, bus (Flixbus, Greyhound), train, car, 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

    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
    5h 57m
    $151–465

  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
    5. Take the bus from Big Pine Key - CVS / MM30 to N Roosevelt & 3rd Streetbus bus Lks
    33h 2m
    $251–406

  3. Train, bus

    1. Take the train from Martinsburg Amtrak Station to Hollywood Amtrak Stationtrain train
    2. Take the bus from Miami Airport Station to Big Pine Keybus bus
    3. Take the bus from Big Pine Key - CVS / MM30 to N Roosevelt & 3rd Streetbus bus Lks
    39h 10m
    $509–1,015

  4. Drive 1,214.7 mi

    1. Drive from Winchester to Key Westcar car 1,214.7 mi
    21h 51m
    $222–321

  5. Bus to Ronald Reagan Washington National Airport, fly

    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
    6h 35m
    $196–728

  6. Taxi to Hagerstown Regional Airport, fly

    1. Take the taxi from Winchester to Hagerstown-Airport-HGRtaxi taxi
    2. Fly from Hagerstown Regional Airport (HGR) to Key West International Airport (EYW)plane plane HGR - EYW
    6h 57m
    $203–530

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

Calendar41Weekly Planes
Duration4h 59mAverage Duration
Ticket$80Cheapest Price
See schedules

Questions & Answers

Map of how to get from Winchester to Key West.ExpandLaunch map view
  • Distance: 1,103.5 mi
  • Duration: 5h 57m

What companies run services between Winchester, VA, USA and Key West, FL, USA?

You can take a vehicle from Winchester to N Roosevelt & 3rd Street 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, and Big Pine Key - CVS / MM30 in around 33h 2m.

Airlines
Train operators
Bus operators
Other operators

Want to know more about travelling around United States

Rome2Rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.

Related travel guides

Need to know: Greyhound

Read the travel guideNeed to know: Greyhound