Flight
Driving
Medford to Key West
Updated: 28 May 2026
Traveling from Medford to Key West is best done by flying from Boston Logan to Key West International Airport (EYW). Driving takes about 30-32 hours via I-95 and the Overseas Highway. Key West is known for its tropical climate, vibrant nightlife, and beautiful beaches.
Total Distance: Driving distance 3,500 km, straight-line air distance 2,500 km.
Fastest Way
Connecting flight, taking about 8-9 hours total.
Cheapest Way
Driving, especially for groups, is often the most cost-effective.
Compare Medford to Key West Routes
|
Connecting
|
Direct
|
|
|---|---|---|
| Duration | 6 hours | 31 hours |
| Avg Price | $300 - $800 | $500 - $900 (fuel + tolls) |
| Operator | American, Delta | Personal Vehicle |
| Route | BOS to EYW. | I-95 S to US-1 S. |
| Tip | Most flights require a layover in a hub city like Miami or Charlotte. | The drive is very long; plan for multiple overnight stops. |
Travel Tips
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Airport AccessThe airport is close to downtown; rideshare is the best option.
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DiningTry the local seafood and key lime pie at a traditional restaurant.
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BookingBook your hotel in the downtown area for the best experience.
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WeatherKey West is tropical; pack accordingly.
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NavigationUse a GPS to navigate the city, as the layout can be complex.
Safety Tips
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DrivingBe cautious of heavy traffic during rush hour in Key West.
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Personal SafetyStay in well-lit, populated areas when exploring at night.
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Vehicle SecurityAlways lock your car and keep valuables out of sight.
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EmergencyKeep a list of local emergency contacts if you are driving.
People Also Ask
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Is Key West walkable?The downtown area is, but you will need a car for most of the island.
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How long is the flight?Connecting flights take about 8-9 hours.
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Are there direct flights?Direct flights are rare; expect a layover.
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What is the best time to visit?Winter and Spring for the best weather.
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Do I need a car?It is recommended if you plan to explore outside the downtown core.
Quick Info
- From Medford, Massachusetts, United States
- To Key West, Florida, United States
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Modes
Best Time to Travel
Winter and Spring for pleasant weather and outdoor activities.
Things to Do in Key West
1
Southernmost Point
Visit the iconic buoy marking the southernmost point in the continental U.S.
2
Duval Street
Experience the famous nightlife, bars, and restaurants.
3
Ernest Hemingway Home
Tour the historic home of the famous author.
4
Dry Tortugas National Park
Take a ferry to this remote park with beautiful beaches and snorkeling.
Tags
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