Drive Time
4h 57m
Distance
250.1 mi
402 km
Drive Score
8/10
Great drive
Same Day?
Yes, doable
Fuel Cost
$38
one way
Photo: Kei Scampa
Spanning 250.1 miles across Mississippi, this drive from Winona to Gulfport typically takes about 4 hours and 57 minutes of road time. Because it is a straightforward trek, you can easily complete the journey in a single day without needing an overnight stay. Expect to spend approximately $38 on fuel for the trip, depending on your vehicle's efficiency. You will rely heavily on I-55 and US 49 to navigate from the northern interior toward the coast. This route is entirely contained within the Southeast, offering a consistent regional feel as you transition from the rolling landscapes of central Mississippi toward the Gulf Coast. It is an efficient, highway-focused path that prioritizes speed and directness over detours.
Trip Pace
Same-day drive is realistic
A same-day return is possible, but it will make for a full day on the road.
Break Rhythm
1 planned break
Plan on a short reset every 3 to 4 hours to stay fresh behind the wheel.
Midpoint
125 miles from Winona, MS
A natural place for your longest stop of the day , about 2h 23m into the drive .
This trip is heavily weighted toward highway travel, with 95% of your time spent on major routes. You will start with an interstate grind, including the longest uninterrupted stretch of the journey: 89.5 miles on I-55. As you transition onto Highway 49 South and US 49, the character of the drive shifts, though it remains firmly focused on high-speed transit. You should be prepared for a consistent pace behind the wheel rather than technical, winding backroads. The experience is practical and functional, designed to get you from the northern region of the state to the southern coast with minimal navigation stress.
This is a straightforward highway drive that stays mostly on I 55 and Highway 49 South. This route has several spots where lane changes, forks, or exits need your full attention. The trickiest moment comes around 93.3 miles in near US 49.
Demanding - plan breaks and stay ahead of the key maneuvers
This is a demanding drive. With 16 significant decision points across 250.1 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 93.3 miles (US 49): Highway fork - watch signs carefully. Multiple destination signs - pick the right one; at 175.8 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one; at 183.9 miles (US 98): Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one.
These are the spots where you need to pay the most attention. Preview them before you drive.
Keep slight right at fork onto US 49 toward Richland, Hattiesburg
Highway fork - watch signs carefully. Multiple destination signs - pick the right one
Take the exit toward I 59 South: New Orleans, Gulf Coast
Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one
Take the exit onto US 98 toward US 98 East: Lucedale, Mobile
Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one
Take the exit toward US 49: Wiggins, Gulfport, Mississippi Gulf Coast
Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one
Keep slight left at fork toward Multi Purpose Center, Hattiesburg
Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one
Between Winona, MS and Gulfport, MS, road signs point toward Hattiesburg, Richland, Gulf Coast, Mississippi Gulf Coast, Mobile and Multi Purpose Center.
Hattiesburg
Richland
Gulf Coast
Mississippi Gulf Coast
Mobile
Multi Purpose Center
| Road | Distance | Duration |
|---|---|---|
| I 55 | 89.5 mi | 1h 37m |
| Highway 49 South | 80.3 mi | 1h 37m |
| US 49 | 64.7 mi | 1h 20m |
| Lance Corporal Roy M Wheat Memorial Highway | 7.7 mi | 8m |
| US 98 | 3.2 mi | 4m |
| Middleton Road | 1 mi | 1m |
| Dr Martin Luther King Jr Boulevard | 0.7 mi | 1m |
| Summit Street | 0.4 mi | 1m |
Step-by-step road directions between Winona, MS and Gulfport, MS.
Start on South Vine Street
Turn left onto Summit Street
Turn right onto US 51
Turn left onto MS 182
Turn left onto US 82
Take the exit
Merge onto I 55
Take the exit
Keep slight right at fork onto US 49
Merge onto US 49
Continue on US 49; MS 42
Continue on US 49; MS 42
Take the exit
Merge onto I 59
Take the exit onto US 98
Take the exit
Keep slight left at fork
Turn right onto US 49
Turn straight onto US 49
Continue on US 49
Arrive at destination
Since this is a roughly five-hour drive, try to depart early in the morning to avoid fatigue and maximize your time once you reach Gulfport. You only need to plan for one main stop, which allows for plenty of flexibility in your schedule. Keep a close eye on your fuel gauge when traveling along the US 49 segments to ensure you don't run low between major interchanges. Because 95% of the route is highway-based, stay alert for changing traffic patterns as you move between the interstate and the state highway sections. Taking that single planned break midway through the 250.1-mile trek will go a long way in keeping you refreshed for your arrival.
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.
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 80 miles or 1h 30m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 125 miles or 2h 23m in
This is the best place for your longest stop, a real meal, and a full fuel check.
Final approach
Final hour starts around 4h 1m
Traffic, exits, and arrival timing usually matter more near Gulfport, MS than in the middle of the route.
Open the route before leaving Winona, MS 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 Winona, MS
This is one driving day of about 250.1 miles and 4h 57m.
Rest stops, refuel points, and overnight suggestions along this route.
Halfway Point
Midpoint
About 125 mi from Winona, MS · 2h 23m into the drive
Mid-route town
Meal stop
125 mi into the route
Best for: Lunch, fuel, and a longer reset
This sits close to the middle of the route, so it works well for the longest stop of the day.
A short stop after about 80 miles helps settle the day before fatigue starts building.
The midpoint is around 125 miles from Winona, MS, which is a good place for a longer meal and fuel stop.
Before the longest stretch
Fuel checkTop up before I 55 if your tank is already low. That segment runs about 89.5 miles.
The final approach into Gulfport, MS usually feels slower than the middle of the drive, so avoid planning your tightest schedule at the very end.
Try to arrive with enough fuel left to skip an immediate station stop unless you already know the area around Gulfport, MS.
These stop ideas are pacing suggestions — the exact town or exit can change with traffic, hotel plans, and fuel range.
Regular Gas
$38.23 one way
$76.47 round trip
| Fuel Type | $/gal | One Way | Round Trip |
|---|---|---|---|
| midgrade | $4.26 | $41.94 | $83.87 |
| premium | $4.61 | $45.39 | $90.78 |
| diesel | $5.64 | $55.56 | $111.13 |
No toll roads detected on this route.
Estimated Trip Cost (one way, 1 person)
Fuel
$38
Meals
$25–$50
Total
$63–$88
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 87.5 kg one way. Prices: EIA weekly data, 2026-04-06.
Driving Electric?
About $26 in charging · 0 stops · 67% less CO2
| Vehicle Type | kWh | Stops | DC Fast | Home Charge |
|---|---|---|---|---|
| Average EV | 75 | 0 | $26.26 | $12.00 |
| Efficient EV | 62.5 | 0 | $21.88 | $10.00 |
| EV Truck/SUV | 100 | 1 | $35.01 | $16.01 |
Gas CO2
88 kg
EV CO2
29 kg (67% less)
Plan for 0 charging stops, roughly every 270 miles. Allow 25-40 minutes per stop at a DC fast charger.
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. If you're planning ahead, check the forecast closer to your travel date.
Origin
Late night in Winona on Sunday
Local time
5:23 AM
CDT
Current temp
64°F
Forecast unavailable right now
Destination
Late night in Gulfport on Sunday
Local time
5:23 AM
CDT
Current temp
68°F
Forecast unavailable right now
Along the Route
85°F
Magee, MS
125 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
Origin and destination are on the same clock, so arrival timing is easier to judge at a glance.
Temperature spread
A meaningful temperature swing is a good cue to rethink layers, water, and how soon you want to arrive.
Road read
An early start around 7-8 AM gets you there with plenty of daylight left.
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