Spanning 284 miles across New York, this trip from Islip to Southport takes approximately 5 hours and 51 minutes of driving time. Because the route relies on local roads rather than major interstates, you should plan for a full day behind the wheel, though it is manageable as a single-day journey. Expect to spend about $46 on fuel for the trip. Navigating through the Northeast, you will trade the coastal feel of Islip for the inland setting of Southport. Since the drive is turn-heavy and avoids highways entirely, it is best suited for drivers who prefer a hands-on, local road experience over the monotony of high-speed transit.
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
142 miles from Islip, NY
A natural place for your longest stop of the day
, about 3h 3m into the drive
.
Main Roads
Road
Distance
Duration
Christopher Columbus Highway
68.2 mi
1h 20m
I 81
58.1 mi
1h 9m
I 86
54.7 mi
1h 4m
I 380
27.7 mi
30m
Southern State Parkway
24.7 mi
31m
Keystone Shortway
17.3 mi
24m
Cross Bronx Expressway
6.6 mi
8m
Clearview Expressway
5 mi
5m
Longest stretch:
Christopher Columbus Highway
— 68.2 mi, about 1h 20m
Turn-by-Turn Driving Directions
Step-by-step road directions between Islip, NY and Southport, NY.
1
Start on NY 27A
0.8 mi·1 min·Main Street
2
Continue on Montauk Highway
0.2 mi·19 sec·Montauk Highway
3
Continue on NY 27A
1.1 mi·1 min·Main Street
4
Turn right onto 3rd Avenue
0.6 mi·1 min·3rd Avenue
5
Continue on CR 57
0.3 mi·36 sec·Rossevelt Street
6
Continue on CR 57
0.7 mi·1 min·Howells Road
Use the left lane.
7
Turn straight onto Sunrise Highway
163 ft·3 sec·Sunrise Highway
8
Keep slight right at fork onto CR 57
0.3 mi·36 sec·Howells Road
Toward Howells Road, Deer ParkUse the right lane.
9
Continue on CR 57
0.6 mi·1 min·Bay Shore Road
10
Take the ramp
0.1 mi·19 sec
Toward SO West: New York
11
Continue on this road
363 ft·8 sec·this road
12
Merge onto SO
25 mi·31 min·Southern State Parkway
Use the straight / right lanes.
13
Take the exit
0.3 mi·43 sec
Toward Cross Island Parkway North, Whitestone BridgeUse the slight right lane.
14
Merge onto CI
1.3 mi·1 min·Cross Island Parkway
15
Take the exit
317 ft·9 sec
Exit 26BToward NY 24: UBS Arena-Belmont ParkUse the slight right lane.
16
Keep slight left at fork
437 ft·12 sec
Toward NY 24 West: Hempstead AvenueUse the slight left / slight right lanes.
17
Keep slight right at fork
0.1 mi·15 sec
Toward Cross Island Parkway North, Hempstead Avenue West
18
Keep slight right at fork
266 ft·8 sec
Toward Hempstead Avenue WestUse the slight left / slight right lanes.
19
Continue on this road
0.1 mi·13 sec·this road
Toward Grandstand, Hempstead Avenue West
20
Keep slight left at fork
100 ft·4 sec
Toward Hempstead Avenue
21
Turn right onto NY 24
1.0 mi·2 min·Hempstead Avenue
Use the right lane.
22
Turn left onto Jamaica Avenue
0.1 mi·17 sec·Jamaica Avenue
23
Turn right onto NY 24
0.7 mi·1 min·212th Street
24
Continue on I 295
5.0 mi·5 min·Clearview Expressway
Toward I 295 North: Clearview Expressway, Through Neck BridgeUse the straight / slight right lanes.
25
Continue on I 295
2.0 mi·3 min·Throgs Neck Bridge
26
Continue on I 295
0.7 mi·1 min·Throgs Neck Expressway
Use the straight / slight right lanes.
27
Keep slight left at fork onto I 295
6.6 mi·8 min·Cross Bronx Expressway
Use the straight / slight right lanes.
28
Keep slight left at fork onto I 95; US 1
0.7 mi·1 min·Trans-Manhattan Expressway
Toward Upper Level
29
Continue on I 95; US 1
0.6 mi·59 sec·George Washington Bridge (upper level)
30
Continue on I 95 EXPR; US 1 EXPR; US 9 EXPR
0.5 mi·48 sec·I 95 EXPR; US 1 EXPR; US 9 EXPR
31
Keep slight left at fork onto I 95 EXPR; US 1 EXPR; US 9 EXPR
0.6 mi·39 sec·I 95 EXPR; US 1 EXPR; US 9 EXPR
Use the straight / slight right lanes.
32
Keep slight left at fork onto I 95 EXPR; NJTP
0.1 mi·8 sec·I 95 EXPR; NJTP
33
Take the exit
0.2 mi·22 sec
Toward I 95 South, NJTP South: HackensackUse the straight / slight right lanes.
34
Keep slight left at fork
0.4 mi·29 sec
Toward I 95 South, NJTP South: HackensackUse the slight left / slight right lanes.
35
Merge onto I 95; NJTP
2.0 mi·2 min·New Jersey Turnpike
Use the straight / slight right lanes.
36
Take the exit
0.8 mi·1 min
Exit 69Toward I 80 West: Paterson, HackensackUse the straight / slight right lanes.
37
Continue on I 80
68 mi·1 hr 20 min·Christopher Columbus Highway
Use the straight / slight right lanes.
38
Keep slight left at fork onto I 80
5.5 mi·8 min·Keystone Shortway
Use the straight / slight right lanes.
39
Keep slight left at fork onto I 80
12 mi·15 min·Keystone Shortway
40
Take the exit
0.7 mi·46 sec
Exit 293Toward I 380 North: Scranton
41
Continue on I 380
28 mi·30 min·I 380
Use the straight lane.
42
Merge onto I 81
58 mi·1 hr 9 min·I 81
Use the straight lane.
43
Keep slight left at fork onto I 86; NY 17
55 mi·1 hr 4 min·I 86; NY 17
Toward I 86: Corning
44
Take the exit
0.2 mi·27 sec
Exit 56Toward NY 352: Elmira, Jerusalem Hill
45
Keep slight left at fork
103 ft·6 sec
46
Turn left onto NY 352
0.8 mi·1 min·East Water Street
47
Turn left onto Madison Avenue
460 ft·9 sec·Madison Avenue
48
Continue on Sly Street
0.2 mi·22 sec·Sly Street
49
Continue on Pennsylvania Avenue
0.2 mi·23 sec·Pennsylvania Avenue
50
Turn left onto NY 14
2.5 mi·3 min·Clemens Center Parkway
51
Arrive at destination
NY 14
Trip Plan
Given the 5-hour and 51-minute duration, departing early in the morning is your best strategy to avoid mid-day congestion on local roads. With only one recommended stop included in the itinerary, try to pace yourself by taking a break at the halfway mark to stretch your legs and refuel. Keep your $46 fuel budget in mind as you map out your stops, as local roads can sometimes be less convenient for quick refueling than major highway exits. Since this route is entirely off-highway, stay alert for lower speed limits and frequent traffic signals that characterize the local streets along your path. Flexibility is your biggest advantage here, so adjust your pace to account for the technical nature of these specific roads.
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 142 miles from Islip, NY, or about 3h 3m into the drive.
The longest continuous stretch on this route runs about 68.2 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 62 miles or 1h 25m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 142 miles or 3h 3m 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 49m
Traffic, exits, and arrival timing usually matter more near Southport, NY than in the middle of the route.
Before You Leave
+
Open the route before leaving Islip, NY 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 Islip, NY
This is one driving day of about 284 miles and 5h 51m.
Your first comfortable stop window is around 62 miles from Islip, NY.
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 Christopher Columbus Highway for about 68.2 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 32
5 decision points cluster between mile 3.6 and 50.3 — GPS handles the exact turns, but know they're coming. Your lane choice matters more than the turn itself.
9
3.6 mi into trip|~6m in|CR 57 / Howells Road
Keep slight right at fork onto CR 57 / Howells Road toward Howells Road, Deer Park
Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one
Use the right lane.
Toward Howells Road, Deer Park
8
31.1 mi into trip|~43m in
Keep slight left at fork toward NY 24 West: Hempstead Avenue
Highway fork - watch signs carefully. Lane positioning matters here
Use the slight left / slight right lanes.
Toward NY 24 West: Hempstead Avenue
8
31.2 mi into trip|~43m in
Keep slight right at fork toward Hempstead Avenue West
Highway fork - watch signs carefully. Lane positioning matters here
Use the slight left / slight right lanes.
Toward Hempstead Avenue West
8
50 mi into trip|~1h 10m in
Take the exit toward I 95 South, NJTP South: Hackensack
Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one
Use the straight / slight right lanes.
Toward I 95 South, NJTP South: Hackensack
8
50.3 mi into trip|~1h 11m in
Keep slight left at fork toward I 95 South, NJTP South: Hackensack
Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one
Use the slight left / slight right lanes.
Toward I 95 South, NJTP South: Hackensack
Fuel & Cost
Regular Gas
$46.75 one way
$93.50 round trip
$4.18/gal25.4 MPG avg99 kg CO2
Fuel Type
$/gal
One Way
Round Trip
midgrade
$4.52
$50.55
$101.10
premium
$4.92
$55.04
$110.09
diesel
$5.61
$62.70
$125.41
Estimated Tolls: $22.83
George Washington Bridge
$16.00
Throgs Neck Bridge
$6.55
New Jersey Turnpike
(2 mi)$0.28
Toll estimates based on average 2024-2025 rates. EZ-Pass/SunPass discounts may lower the actual cost.
Estimated Trip Cost (one way, 1 person)
Fuel
$47
Tolls
$23
Meals
$25–$50
Total
$95–$120
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 99.4 kg one way.
Prices: EIA weekly data, 2026-04-13.
Driving Electric?
About $30 in charging
· 1 stop
· 67% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
85.2
1
$29.82
$13.63
Efficient EV
71
0
$24.85
$11.36
EV Truck/SUV
113.6
1
$39.76
$18.18
Gas CO2
99 kg
EV CO2
33 kg (67% less)
Plan for 1 charging stop. A 30-minute DC fast charge mid-route should be enough to complete the trip comfortably.
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 13, 2026
Origin
Islip, NY
Late night
in Islip on Sunday
Local time
4:48 AM
EDT
Current temp
67°F
Mostly Cloudy
SW 10 to 17 mph9% chanceLive forecast
Destination
Southport, NY
Late night
in Southport on Sunday
Local time
4:48 AM
EDT
Current temp
41°F
Unavailable
Live forecast
49°F
Ramapo, NY
142 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
26 degrees cooler at arrival
A meaningful temperature swing is a good cue to rethink layers, water, and how soon you want to arrive.
Road read
5h 51m on the road
An early start around 7-8 AM gets you there with plenty of daylight left.
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.
Hamilton Grange National Memorial
National Memorial
Merchant’s clerk, Revolutionary War soldier, first Secretary Treasury of the United States: Alexander Hamilton’s life is memorialized at The Grange, the home he built on a country estate in uptown Man...
The final resting place of President Ulysses S. Grant and his wife, Julia, is the largest mausoleum in North America. It testifies to a people’s gratitude for the man who ended the bloodiest conflict...
Before the 1960s, almost everything about living authentically as a lesbian, a bisexual person or a gay man was illegal. The Stonewall Uprising on June 28, 1969 is a milestone in the quest for civil r...
The African Burial Ground stands as the oldest and largest known excavated burial site in North America for both free and enslaved Africans. It offers a profound testament to the enduring legacy of Af...
Here at Federal Hall, George Washington took the oath of office as the first President of the United States, marking the beginning of the American constitutional republic. This historic site served as...
Located at the southern tip of Manhattan, Castle Clinton marks the place where New York City began and reflects the growth of both the city and the nation. Built to defend the harbor during the War of...
Park data from the National Park Service API. Alerts update every 2 hours.
More Details
What kind of drive is this?
Forget about cruise control for this journey; with a 0% highway share, this route is defined by a turn-heavy, local-road personality. You will spend your time navigating via Montauk Highway, Main Street, and 3rd Avenue, which keeps the pace consistent but requires your full attention. Because there is no long, uninterrupted interstate stretch, the drive maintains a steady, rhythmic flow that keeps you engaged with the changing local surroundings. It is a practical, ground-level way to see the region, though you should be prepared for the constant turning and intersection navigation that comes with avoiding major highways.
65% highway — fuel and pacing are the main things to plan.
51 navigation steps total — most of the decisions cluster near the start and finish.
Longest single stretch: 68.2 mi on Christopher Columbus Highway.
How Hard Is This Drive?
10/10
This is a straightforward highway drive that stays mostly on Christopher Columbus Highway and I 81. This route has several spots where lane changes, forks, or exits need your full attention. The trickiest moment comes around 3.6 miles in near CR 57 / Howells Road.
Driving Effort10/10
High effort - long or complex enough to need steady focus all day
Balances navigation complexity with total wheel time.
This is a demanding drive. With 32 significant decision points across 284 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 3.6 miles (CR 57 / Howells Road): Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one; at 31.1 miles: Highway fork - watch signs carefully. Lane positioning matters here; at 31.2 miles: Highway fork - watch signs carefully. Lane positioning matters here.
Elevation Profile
Gently rolling terrain
1,833 ft12 ft
Total Climb
2,360 ft
Total Descent
1,479 ft
Highest Point
1,833 ft
~142 mi in
Elevation Range
1,821 ft
Towns Mentioned on Route Signs
Based on OSRM destination-sign hints, not a full list of every settlement the road passes.
Between Islip, NY and Southport, NY, road signs point toward Cross Island Parkway North, Hempstead Avenue West, Grandstand, Upper Level, Njtp South: Hackensack and Hackensack.
Islip (pronounced "ICE-lip") is a town on Long Island in the state of New York. Located within Suffolk County, the Town of Islip includes the villages of Brightwaters, Islandia, Ocean Beach and Saltaire. It also includes numerous hamlets including Bay Shore and Sayville which are ferry terminals for Fire Island. Other prominent communities are Bayport, Brentwood, Central Islip, Hauppauge, Islip village (the town seat), and Ronkonkoma.
Top landmarks
•Bayport Aerodrome — airport in Suffolk County, New York, United States
•Connetquot River State Park Preserve — state park in New York
•Modesty — oyster-dredging sloop built in Long Island
Doable as a same-day drive at 5h 51m. Total distance: 284 miles.
Family Friendly
Moderate complexity with 1 natural rest stops along the way.
Solo Traveler
5h 51m drive, comfortable solo distance.
Frequently Asked Questions
The longest stretch is about 68.2 miles on Christopher Columbus Highway. The full list of main roads is in the Roads section above.
Expect about $22.83 in tolls one way, starting with George Washington Bridge. Most Northeast and Midwest toll agencies accept E-ZPass; in the West and Texas, transponders like TxTag or FasTrak apply. If you do not have a transponder, cashless tolling plates will mail a bill to the vehicle's registered address — usually with a surcharge, so a rental-car toll pass is often cheaper than paying by mail.
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 Southport, NY 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 3.6 miles (CR 57 / Howells Road): Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one; at 31.1 miles: Highway fork - watch signs carefully. Lane positioning matters here; at 31.2 miles: Highway fork - watch signs carefully. Lane positioning matters here.
Yes — Hamilton Grange National Memorial, General Grant National Memorial and Stonewall National Monument (6 total within detour distance). See the National Parks section for detour distances and tips on detours.
Not recommended in a single day. At 5.9 hours each way, a round trip means 11.7 hours of driving — that is an unsafe level of fatigue for most drivers. Plan at least one night at Southport, NY before the return drive.
