Traveling from South Boston to Portsmouth covers 161.8 miles across Virginia’s southeast corridor, typically taking about 3 hours and 37 minutes of driving time. Because this is a relatively straightforward journey, you can easily complete it in a single day without needing an overnight stay. Expect to budget roughly $26 for fuel, depending on your vehicle's efficiency. This highway-focused route transitions you from the inland areas of South Boston toward the coastal environment of Portsmouth. It is a practical, efficient path for travelers looking to bridge these two regions directly. Since the drive is manageable in one sitting, you have the flexibility to depart whenever suits your schedule best.
Trip Pace
Same-day drive is realistic
A same-day return is realistic if you keep stops short.
Break Rhythm
1 planned break
A short stop every 2 to 3 hours is enough for this drive.
Midpoint
80.9 miles from South Boston, VA
A natural place for your longest stop of the day
, about 1h 48m into the drive
.
Main Roads
Road
Distance
Duration
Southampton Parkway
62.1 mi
1h 20m
Clarksville Bypass
22.9 mi
29m
Governor Harrison Parkway
22.5 mi
30m
Bill Tuck Highway
18.1 mi
22m
Pleasant Shade Drive
6.4 mi
8m
I 264
5.5 mi
7m
West Atlantic Street
5.1 mi
6m
Highway 58
3.6 mi
5m
Longest stretch:
Southampton Parkway
— 62.1 mi, about 1h 20m
Turn-by-Turn Driving Directions
Step-by-step road directions between South Boston, VA and Portsmouth, VA.
1
Start on VA 129
91 ft·5 sec·North Main Street
2
Continue on US 501
0.2 mi·39 sec·Main Street
Use the straight / left lanes.
3
Turn left onto VA 304
0.7 mi·1 min·Seymour Drive
4
Turn right onto US 360
0.2 mi·19 sec·James D Hagood Highway
5
Continue on US 360
0.4 mi·43 sec·John Randolph Boulevard
6
Turn left onto US 58
18 mi·22 min·Bill Tuck Highway
Use the left / straight lanes.
7
Continue on US 58; VA 49
3.6 mi·4 min·Clarksville Bypass
Use the straight lane.
8
Keep slight right at fork onto US 58
19 mi·24 min·Clarksville Bypass
Toward US 58 East: Boydton, South Hill
9
Continue on US 1; US 58
3.5 mi·4 min·Highway 1
10
Continue on US 58
3.3 mi·4 min·South Hill Bypass
11
Continue on US 58
1.1 mi·1 min·East Atlantic Street
12
Continue on US 58
3.6 mi·5 min·Highway 58
13
Continue on US 58
1.2 mi·2 min·Piney Pond Road
14
Continue on US 58
23 mi·30 min·Governor Harrison Parkway
15
Continue on US 58
6.4 mi·8 min·Pleasant Shade Drive
16
Continue on US 58
5.1 mi·6 min·West Atlantic Street
17
Continue on US 58
62 mi·1 hr 20 min·Southampton Parkway
Use the straight / slight right lanes.
18
Continue on US 13; US 58; US 460
1.7 mi·2 min·West Military Highway
19
Take the exit onto US 13; US 460
0.7 mi·1 min·US 13; US 460
Toward I 264 East, I 64, US 13 North: Portsmouth, Norfolk, Va Beach
20
Keep slight left at fork onto US 13; US 460
0.4 mi·56 sec·US 13; US 460
Toward I 264 East, I 64, US 13 North: Portsmouth, Norfolk, Va Beach
21
Merge onto I 664; US 13; US 460
0.6 mi·42 sec·Hampton Roads Beltway
22
Take the exit
0.8 mi·1 min
Exit 15AToward I 264 East: Portsmouth, Norfolk
23
Continue on I 264
5.5 mi·7 min·I 264
Use the straight / slight right lanes.
24
Take the exit
0.2 mi·20 sec
Exit 7BToward VA 141 North: Effingham Street, Crawford StreetUse the slight right lane.
25
Keep slight left at fork
0.2 mi·30 sec
Toward Crawford Street, Downtown, PortsmouthUse the straight / right lanes.
26
Turn slight left onto Pavilion Drive
0.2 mi·29 sec·Pavilion Drive
Use the straight lane.
27
Turn right onto Bart Street
368 ft·7 sec·Bart Street
28
Enter roundabout onto Crawford Street
285 ft·6 sec·Crawford Street
29
Continue on Crawford Street
0.2 mi·26 sec·Crawford Street
30
Turn left onto High Street
165 ft·12 sec·High Street
Use the left lane.
31
Arrive at destination
High Street
Trip Plan
To make the most of this 161.8-mile drive, plan for at least one dedicated stop to stretch your legs and refresh. Since the journey takes nearly four hours, leaving early in the morning can help you avoid potential traffic buildup as you reach the more populated Portsmouth area. Keep an eye on your fuel gauge, as the $26 estimated cost can fluctuate based on local pricing along the parkways. Because you only have one planned stop, use that break strategically to refuel or grab a snack rather than rushing through the transit. Staying mindful of the 62.1-mile stretch on Southampton Parkway will help you pace your driving effectively throughout the day.
Morning Departure
An early start around 7-8 AM gets you there with plenty of daylight left.
Evening Departure
A late afternoon start means arriving after dark. Morning is better.
You can normally do this drive in one day.
Plan roughly 1 meaningful break for fuel, food, and rest.
The halfway point lands around 80.9 miles from South Boston, VA, or about 1h 48m into the drive.
The longest continuous stretch on this route runs about 62.1 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 36 miles or 46m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 80.9 miles or 1h 48m in
This is the best place for your longest stop, a real meal, and a full fuel check.
Final approach
Final hour starts around 2h 56m
Traffic, exits, and arrival timing usually matter more near Portsmouth, VA than in the middle of the route.
Before You Leave
+
Open the route before leaving South Boston, VA so your first major turns are already loaded.
+
Leave with enough water and a charging cable within reach, not packed away.
+
Check your fuel range against the first long segment, especially if you are starting outside city service areas.
Day 1
Settle into the route from South Boston, VA
This is one driving day of about 161.8 miles and 3h 37m.
Your first comfortable stop window is around 36 miles from South Boston, VA.
This route can stay practical as a one-day drive if traffic stays reasonable.
Plan about 1 real break rather than only quick fuel stops.
The longest stretch is on Southampton Parkway for about 62.1 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 14
5 decision points cluster between mile 23.2 and 161 — GPS handles the exact turns, but know they're coming. Your lane choice matters more than the turn itself.
6
23.2 mi into trip|~30m in|US 58 / Clarksville Bypass
Keep slight right at fork onto US 58 / Clarksville Bypass toward US 58 East: Boydton, South Hill
Highway fork - watch signs carefully. Multiple destination signs - pick the right one
Toward US 58 East: Boydton, South Hill
6
153.6 mi into trip|~3h 24m in|US 13; US 460
Keep slight left at fork onto US 13; US 460 toward I 264 East, I 64, US 13 North: Portsmouth, Norfolk, Va Beach
Highway fork - watch signs carefully. Multiple destination signs - pick the right one
Toward I 264 East, I 64, US 13 North: Portsmout...
6
154.6 mi into trip|~3h 26m in
Take the exit toward I 264 East: Portsmouth, Norfolk
Exit ramp - move to the correct lane early. Multiple destination signs - pick the right one
Exit 15A
Toward I 264 East: Portsmouth, Norfolk
8
160.8 mi into trip|~3h 34m in
Take the exit toward VA 141 North: Effingham Street, Crawford Street
Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one
Use the slight right lane.
Exit 7B
Toward VA 141 North: Effingham Street, Crawford...
9
161 mi into trip|~3h 35m in
Keep slight left at fork toward Crawford Street, Downtown, Portsmouth
Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one
Use the straight / right lanes.
Toward Crawford Street, Downtown, Portsmouth
Fuel & Cost
Regular Gas
$25.30 one way
$50.60 round trip
$3.97/gal25.4 MPG avg57 kg CO2
Fuel Type
$/gal
One Way
Round Trip
midgrade
$4.34
$27.67
$55.33
premium
$4.70
$29.95
$59.89
diesel
$5.61
$35.72
$71.45
No toll roads detected on this route.
Estimated Trip Cost (one way, 1 person)
Fuel
$25
Meals
$25–$50
Total
$50–$75
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 56.6 kg one way.
Prices: EIA weekly data, 2026-04-13.
Driving Electric?
About $17 in charging
· 0 stops
· 67% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
48.5
0
$16.99
$7.77
Efficient EV
40.5
0
$14.16
$6.47
EV Truck/SUV
64.7
0
$22.65
$10.36
Gas CO2
57 kg
EV CO2
19 kg (67% 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 18, 2026
Origin
South Boston, VA
Morning
in South Boston on Sunday
Local time
6:20 AM
EDT
Current temp
59°F
Unavailable
Live forecast
Destination
Portsmouth, VA
Morning
in Portsmouth on Sunday
Local time
6:20 AM
EDT
Current temp
62°F
Unavailable
Live forecast
80°F
Emporia, VA
81 mi in
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
3 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
3h 37m on the road
Use the two city cards together: check the sky where you start, then compare it with the local time and temperature at arrival.
Weather data from the National Weather Service. Conditions may change; check closer to your travel date.
National Parks Near This Route
Worth a detour if your schedule allows.
Fort Monroe National Monument
National Monument
Fort Monroe's story spans from prehistory to the 2000s. Kecoughtan Indians occupied Old Point Comfort before the arrival of English colonists. The first enslaved Africans arrived in 1619. Those escapi...
13 mi from route
~31 min detour
Free
near mile 161.8
Park Closure: Road Closure and Fishing Pier Impact
Park data from the National Park Service API. Alerts update every 2 hours.
More Details
What kind of drive is this?
This trip is defined by a highway-focused profile, with 61% of your journey spent on high-speed roads. You will rely primarily on Southampton Parkway, the Clarksville Bypass, and Governor Harrison Parkway to make progress. The longest uninterrupted stretch occurs on Southampton Parkway, where you can settle into a steady rhythm for 62.1 miles. While the route feels fast and efficient, be prepared for the transitions between these primary corridors. You will find that the road maintains a consistent, functional character, allowing you to move steadily through the landscape without the technical complexity of smaller secondary roads.
61% highway — fuel and pacing are the main things to plan.
31 navigation steps total — most of the decisions cluster near the start and finish.
Longest single stretch: 62.1 mi on Southampton Parkway.
How Hard Is This Drive?
8/10
This is a straightforward highway drive that stays mostly on Southampton Parkway and Clarksville Bypass. This route has several spots where lane changes, forks, or exits need your full attention. The trickiest moment comes around 23.2 miles in near US 58 / Clarksville Bypass.
Driving Effort8/10
Demanding - plan breaks and stay ahead of the key maneuvers
Balances navigation complexity with total wheel time.
This is a demanding drive. With 14 significant decision points across 161.8 miles, you will need to stay alert - especially through interchange areas and urban stretches. Consider splitting it into segments if you are not comfortable with fast highway navigation.
Where does it get tricky?
The main spots that need attention: at 23.2 miles (US 58 / Clarksville Bypass): Highway fork - watch signs carefully. Multiple destination signs - pick the right one; at 153.6 miles (US 13; US 460): Highway fork - watch signs carefully. Multiple destination signs - pick the right one; at 154.6 miles: Exit ramp - move to the correct lane early. Multiple destination signs - pick the right one.
Towns Mentioned on Route Signs
Based on OSRM destination-sign hints, not a full list of every settlement the road passes.
Between South Boston, VA and Portsmouth, VA, road signs point toward Hill, Norfolk and Va Beach.
Hill
23.2 mi in|~30m|via US 58
Norfolk
152.8 mi in|~3h 22m|via US 13; US 460
Va Beach
152.8 mi in|~3h 22m|via US 13; US 460
Who Is This Route For?
Weekend Trip
Doable as a same-day drive at 3h 37m. Total distance: 161.8 miles.
Family Friendly
Moderate complexity with 1 natural rest stops along the way.
Solo Traveler
3h 37m drive, comfortable solo distance.
Frequently Asked Questions
The longest stretch is about 62.1 miles on Southampton Parkway. The full list of main roads is in the Roads section above.
We did not find dedicated rest areas on this route. For a drive this long, plan bathroom and stretch breaks around gas stations, fast-food stops, or small-town downtowns — check the Nearby Places section for options.
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 Portsmouth, VA before sunset when you can. Check the Trip Plan for departure windows that land you in daylight.
Only with planning. This is a long drive for kids — consider splitting it into two days rather than pushing through. Plan at least 1 meaningful breaks. Dedicated rest areas are limited, so plan gas or food stops as your bathroom breaks.
The main spots that need attention: at 23.2 miles (US 58 / Clarksville Bypass): Highway fork - watch signs carefully. Multiple destination signs - pick the right one; at 153.6 miles (US 13; US 460): Highway fork - watch signs carefully. Multiple destination signs - pick the right one; at 154.6 miles: Exit ramp - move to the correct lane early. Multiple destination signs - pick the right one.
Yes — Fort Monroe National Monument. See the National Parks section for detour distances and tips on detours.
Possible but tiring. At 3.6 hours each way, an in-and-out day trip would put you behind the wheel for 7.2 hours — manageable with a long break at Portsmouth, VA, but most travelers stay overnight.
