If you are planning a trip from Windsor to Chesapeake, you can expect an 83.1-mile journey that typically takes about 1 hour and 45 minutes to complete. This route is designed as a single-day trip, making it an efficient choice for those looking to travel between these two Southeast Virginia locations without the need for an overnight stay. With a fuel budget of approximately $13, the drive is quite economical for a solo traveler or a small group. You will spend the vast majority of your time on major thoroughfares, as the route is heavily highway-focused. Whether you are commuting or heading out for a quick excursion, this straightforward drive provides a reliable connection across the region.
Trip Pace
Same-day drive is realistic
A same-day return is realistic if you keep stops short.
Midpoint
41.6 miles from Windsor, VA
A natural place for your longest stop of the day
, about 50m into the drive
.
Main Roads
Road
Distance
Duration
VA 33
63.2 mi
1h 11m
Hampton Roads Beltway
6.8 mi
8m
Hampton Roads Bridge-Tunnel
3.5 mi
4m
Chesapeake Boulevard
2.1 mi
3m
Ballentine Boulevard
1.1 mi
1m
East Princess Anne Road
0.9 mi
1m
Wilson Road
0.7 mi
1m
Pocahontas Trail
0.7 mi
1m
Longest stretch:
VA 33
— 63.2 mi, about 1h 11m
Turn-by-Turn Driving Directions
Step-by-step road directions between Windsor, VA and Chesapeake, VA.
1
Start on Gaardahl Drive
256 ft·13 sec·Gaardahl Drive
2
Turn right onto Rasmussen Drive
506 ft·24 sec·Rasmussen Drive
3
Turn right onto Stockholm Drive
0.5 mi·1 min·Stockholm Drive
4
Turn left onto White Oak Road
0.5 mi·1 min·White Oak Road
5
At end of road, turn right onto US 60; VA 33
0.2 mi·15 sec·East Williamsburg Road
6
Continue on US 60; VA 33
0.7 mi·1 min·Pocahontas Trail
7
Turn left onto VA 33
0.2 mi·17 sec·New Kent Highway
Use the left lane.
8
Take the ramp onto VA 33
63 mi·1 hr 11 min·VA 33
Toward I 64 East, VA 33 East: West Point, NorfolkUse the straight / slight right lanes.
9
Keep slight left at fork onto I 64; US 60
342 ft·5 sec·Hampton Roads Beltway
10
Continue on I 64; US 60
3.5 mi·4 min·Hampton Roads Bridge-Tunnel
11
Continue on I 64; US 60
6.7 mi·8 min·Hampton Roads Beltway
Use the straight / slight right lanes.
12
Take the exit
0.2 mi·32 sec
Exit 278Toward VA 194 South: Chesapeake BoulevardUse the slight right lane.
13
Turn straight onto VA 194
2.1 mi·3 min·Chesapeake Boulevard
Use the left lane.
14
Turn straight
135 ft·7 sec
15
Turn left onto VA 247
1.1 mi·1 min·Ballentine Boulevard
16
Turn right onto VA 166
0.9 mi·1 min·East Princess Anne Road
17
Turn left onto VA 166
0.6 mi·1 min·Park Avenue
18
Turn left onto US 460; VA 166; VA 168
0.3 mi·57 sec·East Brambleton Avenue
Use the left / straight / right lanes.
19
Continue on US 460; VA 166; VA 168
0.7 mi·1 min·Campostella Road
20
Turn right onto US 460; VA 166
0.7 mi·1 min·Wilson Road
Use the right lane.
21
Continue on US 460; VA 166
0.3 mi·27 sec·22nd Street
22
Continue on US 460; VA 166
0.3 mi·29 sec·Poindexter Street
Use the straight lane.
23
Turn right onto D Street
412 ft·18 sec·D Street
24
Arrive at destination
D Street
Trip Plan
Because this is a relatively short 1 hour and 45-minute drive, you have plenty of flexibility in your departure schedule. Since the route involves major infrastructure like the Hampton Roads Bridge-Tunnel, it is wise to check for tunnel traffic or roadwork updates before you pull out of Windsor. You won't need to plan for any formal stops along the way given the manageable distance, though keeping your fuel levels monitored for the $13 estimate remains a good best practice. Use the lack of required stops to your advantage by timing your departure to avoid the heaviest regional commute hours. Staying alert while navigating the high-speed transitions between VA 33 and the Hampton Roads Beltway will help ensure you reach Chesapeake smoothly.
Morning Departure
Leave by 9 AM and you'll arrive before lunch.
Evening Departure
Even a 4 PM departure gets you there before dark in summer.
You can normally do this drive in one day.
You may only need one short stretch break if traffic stays light.
The halfway point lands around 41.6 miles from Windsor, VA, or about 50m into the drive.
The longest continuous stretch on this route runs about 63.2 miles.
This is a comfortable same-day trip.
Departure
Before you leave
Start with fuel, water, and navigation already sorted so the first hour feels easy.
First stop
Around 18 miles or 23m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 41.6 miles or 50m in
This is the best place for your longest stop, a real meal, and a full fuel check.
Final approach
Final hour starts around 1h 24m
Traffic, exits, and arrival timing usually matter more near Chesapeake, VA than in the middle of the route.
Before You Leave
+
Open the route before leaving Windsor, VA so your first major turns are already loaded.
Day 1
Settle into the route from Windsor, VA
This is one driving day of about 83.1 miles and 1h 45m.
Your first comfortable stop window is around 18 miles from Windsor, VA.
This route can stay practical as a one-day drive if traffic stays reasonable.
The longest stretch is on VA 33 for about 63.2 miles.
Where to Stop
Rest stops, refuel points, and overnight suggestions along this route.
Place data sourced from public business listings. Hours and availability may vary.
Heads-up: tricky spots
5 of 16
5 decision points cluster between mile 0 and 81.7 — GPS handles the exact turns, but know they're coming. Your lane choice matters more than the turn itself.
5
0 mi into trip|~0m in|Rasmussen Drive
Turn right onto Rasmussen Drive
Navigation decision point
6
2.1 mi into trip|~5m in|VA 33 / New Kent Highway
Turn left onto VA 33 / New Kent Highway
Lane positioning matters here
Use the left lane.
6
2.2 mi into trip|~5m in|VA 33
Take the ramp onto VA 33 toward I 64 East, VA 33 East: West Point, Norfolk
Lane positioning matters here. Multiple destination signs - pick the right one
Use the straight / slight right lanes.
Toward I 64 East, VA 33 East: West Point, Norfo...
7
75.7 mi into trip|~1h 30m in
Take the exit toward VA 194 South: Chesapeake Boulevard
Exit ramp - move to the correct lane early. Lane positioning matters here
Use the slight right lane.
Exit 278
Toward VA 194 South: Chesapeake Boulevard
5
81.7 mi into trip|~1h 42m in|US 460; VA 166 / Wilson Road
Turn right onto US 460; VA 166 / Wilson Road
Lane positioning matters here
Use the right lane.
Fuel & Cost
Regular Gas
$13.00 one way
$25.99 round trip
$3.97/gal25.4 MPG avg29 kg CO2
Fuel Type
$/gal
One Way
Round Trip
midgrade
$4.34
$14.21
$28.42
premium
$4.70
$15.38
$30.76
diesel
$5.61
$18.35
$36.69
No toll roads detected on this route.
Estimated Trip Cost (one way, 1 person)
Fuel
$13
Meals
$25–$50
Total
$38–$63
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 29.1 kg one way.
Prices: EIA weekly data, 2026-04-13.
Driving Electric?
About $9 in charging
· 0 stops
· 66% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
24.9
0
$8.73
$3.99
Efficient EV
20.8
0
$7.27
$3.32
EV Truck/SUV
33.2
0
$11.63
$5.32
Gas CO2
29 kg
EV CO2
10 kg (66% less)
This trip is well within single-charge range for most EVs. No charging stops needed if you start fully charged.
DC fast charging avg $0.35/kWh. Home charging avg $0.16/kWh. US grid CO2: 0.39 kg/kWh.
Travel Intel
Current conditions at both ends of the drive.
Forecast as of Apr 16, 2026
Origin
Windsor, VA
Late night
in Windsor on Sunday
Local time
4:06 AM
EDT
Current temp
60°F
Unavailable
Live forecast
Destination
Chesapeake, VA
Late night
in Chesapeake on Sunday
Local time
4:06 AM
EDT
Current temp
93°F
Mostly Sunny
SW 14 mph0% chanceLive forecast
Special Weather Statement
Special Weather Statement issued April 16 at 1:12PM EDT by NWS Wakefield VA
Red Flag Warning
Red Flag Warning issued April 16 at 9:43AM EDT until April 16 at 7:00PM EDT by NWS Baltimore MD/Washington DC
Seasonal Notes
Summer travel usually means heavier construction, hotter rest stops, and busier weekend traffic around major cities.
Winter travel shortens daylight, so a route that looks manageable on paper can feel much longer after dark.
Holiday weekends tend to make both departure and arrival windows slower than the raw route time suggests.
Time zone
Same local time
Origin and destination are on the same clock, so arrival timing is easier to judge at a glance.
Temperature spread
33 degrees warmer at arrival
A meaningful temperature swing is a good cue to rethink layers, water, and how soon you want to arrive.
Road read
1h 45m on the road
The weather snapshot is not static. If you are leaving later, give both cities one more quick forecast check before departure.
Weather data from the National Weather Service. Conditions may change; check closer to your travel date.
More Details
What kind of drive is this?
The personality of this drive is defined by a significant highway share of 76%, ensuring you spend most of your time at cruising speeds. You will navigate a mix of VA 33, the Hampton Roads Beltway, and the Hampton Roads Bridge-Tunnel as you make your way toward your destination. The longest uninterrupted stretch covers 63.2 miles along VA 33, which serves as the backbone of your journey. Expect the character of the road to shift as you transition from more rural stretches onto the high-traffic corridors of the beltway and tunnel system. Behind the wheel, you should prepare for a consistent, fast-paced experience that requires steady attention to changing traffic patterns.
76% highway — fuel and pacing are the main things to plan.
24 navigation steps total — most of the decisions cluster near the start and finish.
Longest single stretch: 63.2 mi on VA 33.
How Hard Is This Drive?
6/10
This is a straightforward highway drive that stays mostly on VA 33 and Hampton Roads Beltway. You will hit about 16 points where you need to pay attention to lane position or signs. The trickiest moment comes early in the drive near Rasmussen Drive.
Driving Effort6/10
Moderate - straightforward overall, but long enough or busy enough to require pacing
Balances navigation complexity with total wheel time.
This drive requires moderate attention. Across 83.1 miles you will encounter 16 spots where lane choice or exit timing matters. Not difficult for experienced highway drivers, but worth previewing the tricky sections before you go.
Where does it get tricky?
The main spots that need attention: near the start (Rasmussen Drive): Navigation decision point; at 2.1 miles (VA 33 / New Kent Highway): Lane positioning matters here; at 2.2 miles (VA 33): Lane positioning matters here. Multiple destination signs - pick the right one.
Chesapeake is a town of 245,000 people (2019) in the Hampton Roads region of Eastern Virginia. Chesapeake is a diverse city in which a few urban areas are located; it also has many square miles of protected farmland, forests, and wetlands, including a substantial portion of the Great Dismal Swamp National Wildlife Refuge.
Doable as a same-day drive at 1h 45m. Total distance: 83.1 miles.
Family Friendly
Moderate complexity with 0 natural rest stops along the way.
Solo Traveler
1h 45m drive, comfortable solo distance.
First-Time Driver
Mostly highway driving (76%). Some complex stretches to watch for.
Frequently Asked Questions
The longest stretch is about 63.2 miles on VA 33. The full list of main roads is in the Roads section above.
It helps. This route has a higher-than-average number of complex decision points, which get harder in the dark. If the last hour of the trip is on surface roads or mountain grades, aim to arrive at Chesapeake, VA before sunset when you can. Check the Trip Plan for departure windows that land you in daylight.
Yes. At under 2 hours behind the wheel, this works well for families — plan one quick stop if you have younger kids.
The main spots that need attention: near the start (Rasmussen Drive): Navigation decision point; at 2.1 miles (VA 33 / New Kent Highway): Lane positioning matters here; at 2.2 miles (VA 33): Lane positioning matters here. Multiple destination signs - pick the right one.
Yes. A round trip is manageable in a single day if you plan a break at Chesapeake, VA before heading back.
