Is there a train to Key West?

No, the Overseas Railroad was destroyed in a hurricane and never rebuilt.

How long is the drive?

The drive takes approximately 55 to 60 hours of pure driving time.

What is the best airport for Enterprise?

Portland International Airport (PDX) is the primary hub for long-distance travel.

Do I need a passport?

No, this is a domestic route within the United States.

Are there direct flights?

No, you will need at least one connection to reach Key West from Oregon.

Enterprise

Key West

Flight Driving

Enterprise to Key West

Updated: 31 May 2026

Traveling from the Wallowa Mountains of Enterprise to the tropical tip of Key West covers roughly 3,500 miles. The most practical route involves flying from Portland International Airport (PDX) to Key West International Airport (EYW) with at least one connection. Driving is a massive undertaking requiring at least 55 hours of pure road time via I-84 and I-75. You will cross diverse landscapes from the high desert of Oregon to the humid subtropics of the Florida Keys. Expect significant temperature shifts and varied terrain throughout this multi-day transit.

Total Distance: Driving distance 5,600 km, straight-line air distance 4,200 km.

Fastest Way

Flight from PDX to EYW with a single connection takes approximately 9 hours total travel time.

Cheapest Way

Flight from PDX is generally cheaper than the total cost of fuel, hotels, and food for a 5-day drive.

Compare Enterprise to Key West Routes

	Flight Connecting	Driving Direct
Duration	9 hours	58 hours
Avg Price	$500 - $900	$800 - $1,200 in fuel
Operator	Alaska Airlines / American Airlines	Personal Vehicle
Route	PDX to EYW via hubs like DFW or CLT.	I-84 E to I-80 E to I-75 S to US-1 S.
Tip	Book flights departing from PDX rather than regional airports to save on costs.	Ensure your vehicle is serviced for high-altitude mountain passes and flatland heat.

Travel Tips

Airport Transit
Drive from Enterprise to PDX (approx 5 hours) before flying.
Hydration
Drink plenty of water during the flight to combat cabin air dryness.
Packing
Pack layers; Enterprise is cold, while Key West is tropical.
Car Rental
Rent a car in Key West if you plan to explore the outer islands.
Booking
Book your flight at least 3 weeks in advance for better pricing.

Safety Tips

Road Safety
Avoid driving through the Midwest during winter snowstorms.
Sun Protection
Use high-SPF sunscreen in Key West to prevent severe sunburn.
Vehicle Check
Check tire pressure before starting the long drive across the country.
Emergency Kit
Carry a roadside emergency kit including jumper cables and extra water.