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How to get fromWinchester to Kissimmeeby bus, plane, bus (Flixbus), train (Amtrak), car, taxi, or train

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There are 8 ways to get from Winchester to Kissimmee by bus, plane, bus (Flixbus), train (Amtrak), car, taxi, or train

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 Orlando

    best
    1. Take the bus from Front Royal Walmart to Dulles International Airportbus bus
    2. Fly from Washington Dulles International Airport (IAD) to Orlando (MCO)plane plane IAD - MCO
    6h 23m
    $194–548

  2. Drive 868.6 mi

    cheapest
    1. Drive from Winchester to Kissimmeecar car 868.6 mi
    15h 29m
    $159–229

  3. Bus

    1. Take the bus from Crooked Run Park & Ride to 14th St @ F St NWbus bus 611-Fr
    2. Take the bus from Washington Union Station to Orlando Bus Stationbus bus FlixBus N2472 / ...
    21h 42m
    $189–299

  4. Train (Amtrak)

    1. Take the train from Martinsburg Amtrak Station to Kissimmee Amtrak Stationtrain train Floridian
    23h 58m
    $375–765

  5. Taxi to Hagerstown Regional Airport, fly to Orlando Sanford, taxi

    1. Take the taxi from Winchester to Hagerstown-Airport-HGRtaxi taxi
    2. Fly from Hagerstown Regional Airport (HGR) to Orlando Sanford (SFB)plane plane HGR - SFB
    3. Take the taxi from Orlando-Sanford-Airport-SFB to Kissimmeetaxi taxi
    3h 56m
    $287–657

  6. Bus to Ronald Reagan Washington National Airport, fly to Orlando

    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 Orlando (MCO)plane plane DCA - MCO
    7h 1m
    $359–1,171

  7. Taxi, train, train to Baltimore-Washington International Airport, fly to Orlando

    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 Orlando (MCO)plane plane BWI - MCO
    8h 14m
    $215–1,348

  8. Bus to Washington Dulles International Airport, fly to Tampa, train

    1. Take the bus from Front Royal Walmart to Dulles International Airportbus bus
    2. Fly from Washington Dulles International Airport (IAD) to Tampa (TPA)plane plane IAD - TPA
    3. Take the train from Tampa to Kissimmee Amtrak Stationtrain train
    8h 41m
    $174–568

Washington Dulles International Airport (IAD) to Orlando (MCO) flights

Calendar38Weekly Planes
Duration2h 25mAverage Duration
Ticket$49Cheapest Price
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Questions & Answers

Map of how to get from Winchester to Kissimmee.ExpandLaunch map view
  • Distance: 853.2 mi
  • Duration: 6h 23m

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

You can take a vehicle from Winchester to N Main St & W Cypress St 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, Orlando Bus Station, Orlando, and Florida Mall in around 21h 42m. Alternatively, Amtrak operates a train from Martinsburg Amtrak Station to Kissimmee Amtrak Station once daily. Tickets cost $320–700 and the journey takes 23h 32m.

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