Deep South USA Road Trip: New York to Miami Itinerary | Two for the Row'd
← Back to Two for the Row'dTwo for the Row'd 🇮🇪
🇺🇸 USADeep South Road Trip14 states · 4,000km · 13 nights

New York to Miami —
our Deep South USA road trip

Two weeks, more than 4,000 kilometres and a route that changed character almost every day. This is the hub for our full journey, with separate first-hand guides for the stops where we have enough to tell the story properly.

Watch our trip highlights 🎬

🗽 New York→🔔 Philadelphia→🏛️ Washington DC→🏘️ Williamsburg→🏔️ Roanoke→🌲 Gatlinburg & Smokies→🎸 Nashville→🎶 Memphis→📍 Jackson→🎺 New Orleans→🏖️ Pensacola→🎢 Orlando→🚀 Kennedy Space Center→🌴 Miami
🚗 Road Trip at a Glance
🛣️ RouteNew York → Miami
📏 Distance~4,000 km / 2,500 miles
🌙 Trip length13 nights
🇺🇸 States14 states
📍 Main stops15 destinations
📅 Best timeSpring or autumn
🚌 How we did itOrganised tour (transport & hotels sorted)
🚗 Self-drive?Yes — with careful planning
🏨 Pace1–2 nights per stop
🎯 Great forFirst-time USA visitors & big itineraries
🚗 The Road Trip Story

What a trip. What a country.

"Every stage felt different — historic East Coast cities, Colonial Williamsburg, the Blue Ridge and Smokies, Tennessee music country, New Orleans, the Gulf Coast and finally Florida."

We did the journey as an organised 13-night tour from New York to Miami, covering more than 4,000 kilometres and 14 states. The transport, hotels and overall route were taken care of, leaving us to enjoy each stop.

Some places became much bigger highlights than we expected: we loved quaint Williamsburg, Dolly Parton's Stampede was brilliant, Graceland was a standout, and New Orleans gave us both our Steamboat NATCHEZ dinner cruise and Oak Alley Plantation. Florida then brought Kennedy Space Center, the Everglades and the finish line in Miami.

🗺️ Our New York to Miami Route

The route at a glance

Our 13-night journey from New York to Miami, travelling through the East Coast, Virginia, the Great Smoky Mountains, Tennessee, the Deep South and Florida.

Map of our New York to Miami Deep South USA road trip route

Our New York to Miami route — 13 nights through the eastern USA and Deep South.

🗺️ Explore the Trip by Destination

Our Deep South & Florida guides

Open the places where we've built a full first-hand guide. Smaller overnight stops stay in the route below unless we have enough material to make a worthwhile page.

Also on the route: Roanoke, Jackson, Pensacola and Orlando.

📅 The Route

13 nights — New York to Miami

Opening leg
🗽 New York → Philadelphia → Washington DC

We started in New York, stopped in Philadelphia and continued to Washington DC.

Virginia
🏘️ Washington DC → Williamsburg → Roanoke

Williamsburg was one of the loveliest surprises of the trip before the route continued west through Virginia and Roanoke.

Mountains & Tennessee
🏔️ Roanoke → Gatlinburg & Great Smoky Mountains → Nashville → Memphis

The Blue Ridge and Smokies led us into Tennessee, Dolly Parton's Stampede, Nashville's country music and then Memphis and Graceland.

Deep South
🎶 Memphis → Jackson → New Orleans

We travelled through Jackson before reaching New Orleans, where our stay included the Steamboat NATCHEZ dinner cruise and Oak Alley Plantation.

Gulf Coast & Florida
🏖️ New Orleans → Pensacola → Orlando → Kennedy Space Center → Miami

The final leg crossed the Gulf Coast into Florida, with Orlando and Kennedy Space Center before the journey finished in Miami. Our Everglades visit belongs to the South Florida part of the trip rather than being a separate overnight stop on the route.

💡 Practical Road Trip Info

What we'd tell a friend planning the same route

🧭 Book the Tour We Did

Want to follow a similar route?

We did this as an organised tour, which meant the transport, accommodation and route were taken care of while we concentrated on enjoying each stop. Here's a comparable Deep South tour you can book directly through TourRadar.

Disclosure: Affiliate link — we may earn a commission at no extra cost to you.

🎟️ Book Activities Along the Route

Skip-the-line tickets & local tours by city

Tap any city below to see available GetYourGuide activities for that stop — tickets, tours and experiences you can book in advance.

🗽 New York activities & tickets
Powered by GetYourGuide
🎸 Nashville activities & tickets
Powered by GetYourGuide
🎶 Memphis activities & tickets
Powered by GetYourGuide
🎺 New Orleans activities & tickets
Powered by GetYourGuide
🌴 Florida activities & tickets
Powered by GetYourGuide

Disclosure: These are affiliate links. If you book through them we may earn a small commission at no extra cost to you.

❓ Road Trip FAQ

Deep South USA FAQ

How long was our Deep South road trip?
Our route ran for 13 nights from New York to Miami and covered more than 4,000 kilometres through 14 states.
What were our biggest highlights?
Graceland was a standout, and we also loved Williamsburg, Dolly Parton's Stampede, New Orleans, Oak Alley Plantation, Kennedy Space Center and the Everglades.
Did we travel independently?
We did this route as an organised tour, which took care of the transport, accommodation and overall itinerary while still giving us time to experience each stop.
Can I do this route independently instead of on a tour?
Absolutely — many people drive this route independently. The biggest things to plan for are one-way rental car drop-off fees (which can be significant when picking up in New York and dropping off in Miami), booking accommodation well ahead in busy stops like Nashville and New Orleans, and building in enough driving time between stops. If you'd rather have the transport and hotels sorted for you, we did ours as an organised tour.
What is the best time of year to drive New York to Miami?
Spring (March to May) and autumn (September to November, with a caveat about hurricane season) are generally the best windows — mild temperatures right along the route, and the Deep South and Florida haven't hit peak humidity yet. Summer is doable but very hot in the South. Winter works well for Florida but the northern legs can be cold, and mountain routes through the Smokies can be affected by weather.
How many nights should we allow for this route?
We did it in 13 nights and that felt right — enough time to properly explore the big stops (New York, Washington DC, Nashville, Memphis, New Orleans, Miami) while still keeping momentum. You could compress it into 10 or 11 nights if you cut a stop or two, or extend to 16–18 to add extra nights in New Orleans and Miami. Under 10 nights and you're spending too much time driving.
Where can I read the individual city guides?
This page is the road-trip hub. Our separate guides currently cover New York, Philadelphia, Washington DC, Williamsburg, Gatlinburg and the Great Smoky Mountains, Nashville, Memphis, New Orleans, Kennedy Space Center, the Everglades and Miami.
New York to Miami road trip Deep South USA road trip 14 states road trip East Coast USA road trip Two-week USA drive Graceland trip Oak Alley Plantation Kennedy Space Center trip USA southern road trip NY to Miami itinerary
🇺🇸 More USA Adventures