How far is Winchester, VA from Virginia Beach, VA?
The driving distance from Winchester, VA to Virginia Beach, VA is about 237.3 miles (381.9 km), with a travel time of about 04h 05m by car.
- The straight-line flight distance is about 200.3 miles (322.4 km).
- For a round trip, plan for roughly 08h 11m of driving time before adding stops, traffic, or weather delays.
- A comfortable departure window is usually 6:00 AM to 8:00 AM EDT.
Reverse, save, or send this route
This drive is better planned with a longer stop or an overnight stay. Copy the route link, send it to another device, or print a clean version before you head out.
This drive is better planned with a longer stop or an overnight stay.
Flight Distance
Driving Distance
Gas Cost Calculator
Leave and Arrive Planner
Pick a departure time to see your estimated arrival and same-day return window.
Drive time stays fixed at 04h 05m.
An early departure helps you fit a real stop into the day without turning the return into a late-night drive.
This departure sits inside the recommended comfort window for the route.
Halfway Point
A useful midpoint for breaks, coffee, or meeting in the middle.
Town in Virginia, United States
Route Weather Snapshot
Check the forecast at both ends before you head out.
Mostly Sunny
Sunny
Driving Route Map
The map below follows the saved road route between Winchester and Virginia Beach.
Turn-by-Turn Driving Directions
Step-by-step road directions between Winchester and Virginia Beach.
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1
Start on North Cameron Street
742 ft · 33 sec · North Cameron Street
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2
Turn left onto East Boscawen Street
130 m · 18 sec · East Boscawen Street
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3
Turn right onto South Kent Street
3092 ft · 1 min · South Kent Street
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4
Turn left onto Millwood Avenue
1.2 km · 2 min · Millwood Avenue
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5
Turn left onto Millwood Avenue
1105 ft · 40 sec · Millwood Avenue
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6
Continue on Millwood Pike
5.7 mi · 9 min · Millwood Pike
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7
Continue on John Mosby Highway
2.1 mi · 3 min · John Mosby Highway
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8
Continue on John Singleton Mosby Highway
8.8 mi · 12 min · John Singleton Mosby Highway
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9
Turn right onto Winchester Road
7.8 mi · 13 min · Winchester Road
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10
Keep slight left to continue on I 66 East, US 17 South, VA 55 East: Marshall, Fredericksburg
5 mi · 6 min
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11
Take the exit slight right toward US 17: Warrenton, Fredericksburg
1330 ft · 33 sec
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12
Keep slight right
545 ft · 13 sec
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13
Merge slight left onto Winchester Road
2.4 mi · 3 min · Winchester Road
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14
Continue on James Madison Highway
6.5 mi · 9 min · James Madison Highway
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15
Keep slight right to continue on Eastern Bypass
4.9 mi · 7 min · Eastern Bypass
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16
Continue on James Madison Highway
5.1 mi · 7 min · James Madison Highway
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17
Keep slight right to continue on US 17 South
26.8 mi · 39 min
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18
Take the exit straight toward I 95 South, US 17 South: Richmond
47.9 mi · 53 min
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19
Take the exit slight left toward I 295 South: Williamsburg, Norfolk, Va Beach
1.9 mi · 2 min
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20
Merge slight right onto Korean War Veterans Memorial Highway
13 mi · 14 min · Korean War Veterans Memorial Highway
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21
Take the exit slight right toward I 64 East: Norfolk, Virginia Beach
1.3 mi · 3 min
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22
Merge slight left
66.8 mi · 1 hr 15 min
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23
Keep slight left to continue on Hampton Roads Beltway
104 m · 5 sec · Hampton Roads Beltway
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24
Continue on Hampton Roads Bridge-Tunnel
3.5 mi · 5 min · Hampton Roads Bridge-Tunnel
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25
Continue on Hampton Roads Beltway
11.9 mi · 15 min · Hampton Roads Beltway
-
26
Take the exit slight right toward I 264 East, I 264 West: Va Beach, Downtown Norfolk, Portsmouth
914 ft · 14 sec
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27
Keep slight left to continue on I 264 East: Va Beach
3229 ft · 1 min
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28
Merge slight right onto Virginia Beach-Norfolk Expressway
11.8 mi · 16 min · Virginia Beach-Norfolk Expressway
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29
Continue on 21st Street
2247 ft · 54 sec · 21st Street
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30
Turn left onto Arctic Avenue
1553 ft · 46 sec · Arctic Avenue
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31
Turn right onto 25th Street
139 m · 12 sec · 25th Street
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32
Arrive at your destination
0 m · 1 sec · 25th Street
Car Route Details
A richer read on the saved driving route between Winchester and Virginia Beach.
Highway-focused drive
Most of the mileage stays on named highways, so the important moments are ramps, exits, merges, and the final local approach.
I 64 East
Merge slight left
66.8 mi · 01h 15m
Route Summary
A quick read on whether this route feels easy, ambitious, or worth planning around.
A longer out-and-back drive
This is still possible in one day, but it becomes a long driving day. Leaving early and planning your stop window matters more here.
Mostly Sunny leaving Winchester and Sunny near Virginia Beach.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Winchester to Virginia Beach?
The road trip is about 237.3 miles (381.9 km) and usually takes 04h 05m in normal driving conditions.
Is this a same-day trip or an overnight route?
This is still possible in one day, but it becomes a long driving day. Leaving early and planning your stop window matters more here.
What is the halfway point on this route?
Ashland is a useful midpoint, sitting about 118.5 miles from Winchester and 118.8 miles from Virginia Beach.
How much longer is the road route than the straight-line distance?
The direct path is about 200.3 miles (322.4 km), while the road route adds roughly 37 extra miles because roads do not follow the straight air line.
When is the best time to leave for this route?
A good departure window is usually 6:00 AM to 8:00 AM EDT. If you want a more comfortable same-day return, try to leave by 8:48 AM EDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $33.15 one way or $66.31 round trip. Estimated CO2 is about 74.4 kg one way.
What should you check before leaving?
Before you leave, expect Mostly Sunny around Winchester and Sunny near Virginia Beach.
Stop Ideas Near Ashland
Useful break, food, and waypoint ideas within about 15 miles of the route midpoint.
Town Hall
Transit and Meeting Points
Useful pickup, handoff, or rendezvous points close to Ashland.
Ashland
Richmond Staples Mill Road station
Richmond Main Street Station
Petersburg station
Flight Path Map
This map shows the direct air route between Winchester and Virginia Beach. Straight-line distance: 200.31 mi (322.36 km).
#1 Winchester
Independent city in Virginia, United States
| Population | 27,700 |
| Coordinates | 39.1856600, -78.1633300 |
| Altitude | 216 |
| Country | United States |
#2 Virginia Beach
The most populous city in Virginia, Virginia Beach is a major center for tourism, military, and business.
| Population | 451,231 |
| Coordinates | 36.8529300, -75.9779900 |
| Altitude | 3 |
| Country | United States |
End: 25th Street (-75.978051, 36.853145)
Estimated Travel Time
Distance: 382 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 07h 54m |
| 40 mph (64.37 km/h) | 05h 55m |
| 50 mph (80.47 km/h) | 04h 44m |
| 60 mph (96.56 km/h) | 03h 57m |
| 70 mph (112.65 km/h) | 03h 23m |
| 80 mph (129 km/h) | 02h 57m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.96 | $33.15 | $66.31 |
| Mid-grade | $4.43 | $37.07 | $74.14 |
| Premium | $4.78 | $39.99 | $79.98 |
| Diesel | $5.62 | $47.07 | $94.15 |
Assumes 8.3 L/100 km (about 28.3 MPG). CO2 is an estimate and varies by vehicle, fuel blend, traffic, and terrain.
Prices in Virginia · May 19, 2026
Distance to Other Cities
Planning a road trip? See the full trip guide on Trip.ovh — stops, fuel costs, weather, and departure timing.