Southern United States Road Trip
This Southern United States road trip runs from Clearwater Beach (Gulf Coast sunsets) to St. Augustine (America’s oldest city), Jekyll Island (quiet Golden Isles), Savannah (squares + Spanish moss), Charleston (Lowcountry romance), up to Asheville (Blue Ridge arts), then across Tennessee—Knoxville, Nashville, and Chattanooga—for mountains, music, and riverfront views.
We drove each segment, keeping our schedule in mind, but enjoying the scenery as we went. Below is the route, ideal timing, and exactly what to do in each stop.
We consider our itinerary the ultimate Southern United States road trip for friends. We were with another couple and enjoyed each leg of the trip.
Route at a Glance (Miles/Hours are Approximate)
Clearwater Beach → St. Augustine: 200–230 miles • 3.5–4.5 hrs
St. Augustine → Jekyll Island, GA: 80–100 miles • 1.5–2 hrs
Jekyll Island → Savannah, GA: 90–100 miles • ~2 hrs
Savannah → Charleston, SC: ~110 miles • ~2 hrs
Charleston → Asheville, NC: 260–270 miles • 4.5–5.5 hrs (mountain driving)
Asheville → Knoxville, TN: 115–130 miles • 2–2.5 hrs
Knoxville → Nashville, TN: 180–200 miles • 2.5–3 hrs
Nashville → Chattanooga, TN: 130–140 miles
Day 1 & 2: Clearwater Beach, Florida (Gulf Coast Kickoff)
Why go here: Powdery sand, walkable beach strip, postcard sunsets.
Do: Pier 60 sunset stroll, a half-day shelling cruise, Dunedin or Tarpon Springs side trips if you have time. Clearwater Marine Aquarium is a must-visit.
Eat/Sunset Toast: Waterfront grouper sandwiches, sunset cocktails at the Sandbar Tiki on the beach.
Tip: Park once and move on foot or trolley; aim for a sunset arrival to set the mood.
Where to Stay on Clearwater Beach – many options are vailable, but the Opal Sands on the beach is our choice.
Our Notes: You could spend a week in Clearwater Beach and many people do. This is one of the top three family beaches in Florida.
Day 3: St. Augustine, Florida
Why Go Here: As the oldest city in America, we seem to find something new (that is really old!) each time we are here.
Vibe: Cobblestones, Spanish colonial history, live music patios.
Do: Historic district walk, lighthouse climb, Anastasia State Park beach time, Lightner Museum, St. George Street Shops.
Romance move: Carriage ride at dusk, then dinner under string lights.
Where to Stay in St. Augustine – While all the major branded hotels are in the city, our favorite is a downtown hotel called Casa Monica (part of the Marriott). Its central location allows you to walk the entire Historic District and the hotel has its own historic vibe.
Our Notes: We have been to St. Augustine several times and loved each visit. If you are a history buff, there is no other Florida location with more to see.
Day 4: Jekyll Island, Georgia
Why Go Here: One of Georgia’s best known barrier islands. Total visitor centric island for all ages.
Vibe: Quiet, nature-forward; moss-draped oaks and wide beaches.
Do: Driftwood Beach photos, bike the island loop, Jekyll Island Club area.
Detour idea: Quick stop on neighboring St. Simons Island for a pier sunset.
- Where to Stay on Jekyll Island: You have choices from cool VRBOs to resorts. We loved the beachside resort at the Village called The Westin Jekyll Island Beach Resort. It was close to the small Village and right on the beach!
- Our Notes: As first-time visitor, we were totally surprised at the many things to see and do on the island. Don’t miss one of the most unusual beaches you will ever see – Driftwood Beach.
Day 4 & 5: Savannah, Georgia
- Why Go There: Savannah is a true “Southern City”, known for cuisine to match and a busy deep water river port.
Vibe: Squares, live oaks, art & food.
Do: Square-to-square walking tour, Forsyth Park, River Street at night.
Pro tip: Book a late dinner and stroll back—Savannah shines after dark.
- Where to Stay in Savannah: On our trips to Savannah, we have stayed at the Marriott Plant District on the waterfront. Direct access to all the shops, restaurants and bars along River Street.
Our Notes: Some of the most beautiful old Southern mansions remaining in the South. Restoration and preservation in the city is stunning.
Day 6 & 7: Charleston, South Carolina
- Why Go There: No matter what you may have heard about Charleston, nothing will prepare you for the compact downtown area and the fun in this city.
Vibe: Pastel row houses, church steeples, Low-country cuisine.
Do: Rainbow Row, Battery promenade, a harbor or plantation tour. Don’t miss the tour of a WWII Carrier in the harbor and the mile-long shopping on King. Street.
Food note: Shrimp & grits, she-crab soup, benne wafers for the road and an unbelievable coconut cake.
- Where To Stay in Charleston: We stayed at the 100-year-old Planters Inn. It was historic and a classic old hotel. While we loved the old inn, we vowed to stay at the new Charleston Place across the street on our next visit.
- Our Notes: While the entire experience in Charleston was very memorable, two of the restaurants we dined at were exceptional. Try Hall’s Chophouse and Husk for a great southern experience..
Day 7 & 8: Asheville, North Carolina (The Biltmore Estate)
- Why Go There: The Biltmore is nothing short of spectacular! Hurricane devastated Asheville, not so much.
Drive: I-26 climbs into the mountains—take breaks at overlooks.
Do: River Arts District, craft breweries, Grove Arcade, maybe a Blue Ridge Parkway sunset.
The Biltmore Estate –We stayed at The Inn on Biltmore Estate. Stately elegance is the best description. Over 8000 acres of pure manicured farms, a Mansion, a village of shops and restaurants and numerous tours of the winery and farms.
- Our Notes: The highlight of the estate was a tour of the 250-room mansion of George Vanderbilt. Constructed in the early 1900s, it is the ultimate in elegance and excess! One of the most interesting trips we have ever taken. A personal note, my wife saw her first black bear in the wild on the estate!
Day 9: Knoxville, Tennessee
Why Go There: Located in the Appalachian Mountains, there is no way to approach Knoxville without seeing the beauty of its surroundings. The mountains and the Tennessee River combine for picturesque views.
Vibe: University energy meets riverfront walks; gateway to the Smokies.
Do: Market Square and Old City, Sunsphere views, Tennessee River stroll and drive through the campus.
Snack: Hot chicken “lite” or a local BBQ plate – don’t forget the fried catfish Po Boy
Where To Stay in Knoxville – The Embassy Suites by Hilton in downtown met our needs perfectly – including a scenic rooftop bar.
- Our Notes: All four of us were struck by the cleanliness of the city and University of Tennessee campus. Few college towns could match UT’s manicured streets, clean buildings and riverside location. The mountainous views on the way here were stunning.
Day 9 & 10: Nashville, Tennessee
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Why Go There: There are only a handful of places in the United States that could come close to the round-the-clock entertainment of Nashville – maybe New Orleans or Key West could come close. If you like music, famous people with famous bars and 24-hour photo opps, Nashville is the place!
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Vibe: Undisputed music capital. The sounds of live music fill the streets day and night.
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Do: Ryman Auditorium, Broadway honky-tonks, 12 South murals, live songwriter rounds – pick your famous bar- tons of them!
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Tip: Reserve a listening-room show for an intimate night (less touristy, more magic).
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Where to Stay in Nashville: Your best choice for a hotel in Nashville is the Hilton Downtown. There is no hotel that is just steps away from the beat on Broadway and next door to the Arena where all the major stars have concerts. Nothing fancy, just close to the action.
- Our Notes: Maybe a hint of how much fun we had in Nashville was that by late on the second day, we were looking for a quiet, nice restaurant to relax nearby. A stroll through downtown on our second day found the old Printers Alley that was the beginning of the music scene in Nashville 50 years ago. We found The Palm next to our hotel – the crowds, music and bright neon lights were left a block away – at least for an hour or two!
Day 11: Chattanooga, Tennessee (Finish with Views)
Why Go There: Besides being another charming Southern town on the Tennessee River, Chattanooga is the quintessential Southern riverfront town. They center the activities along the waterfront.
Vibe: River, waterfront, paddlewheel boats and southern cooking.
Do: Walnut Street Pedestrian Bridge, Bluff View Art District, Incline Railway/Lookout Mountain.
Where To Stay in Chattanooga: Another riverside hotel with a rooftop bar was our choice. The Edwin Hotel Autograph Collection was our choice.
Our Notes: Our hotel was a block away from the Tennessee Aquarium, which is one of the best in the South. Shops and restaurants line the waterfront. Downtown is walkable. Try Scotties on the River for some good food.
When to Go (and Why)
Best overall: Spring (Mar–May) and Fall (Sep–Nov) for mild temps, fewer storms, and mountain color.
Summer: Beach and river fun—but hot/humid; plan early starts and AC breaks.
Hurricane season (Jun–Nov): Coastal legs are fine with a flexible plan—watch forecasts.
Winter: Quieter coasts; mountain nights can be chilly.
Why We Chose August: We reside in Florida. People in the south were discussing the “hot” temperatures, but they were lower than we were used too. August is a slow time for hotels, restaurants and attractions. Prices were lower, crowds were smaller and reservations were easy to get.
What to Book in Advance
Historic district hotels in St. Augustine, Savannah, and Charleston. All three stay busy year-round.
Biltmore Estate tickets are popular – even on rainy days, the lines can be long
Nashville shows (Ryman, Opry, listening rooms).
Boat tours (sunset sails, shelling, dolphin cruises) on the Florida/Georgia coast legs.
Scenic Detours We Love
A1A between St. Augustine and the Georgia line for ocean views. The Mayport Ferry can be a fun option along A1A.
US-17 (Coastal Highway) Savannah to Charleston for marsh vistas and small-town stops (Beaufort, SC, if you want extra charm).
Blue Ridge Parkway near Asheville for sunrise/sunset overlooks.
What to Pack (Road-Trip Essentials)
Coast & city: Reef-safe sunscreen, packable hats, walking shoes, light layers for air-conditioned restaurants.
Mountains: Light fleece or shell, comfy day-hike shoes, water bottle.
Car kit: Toll transponder or app, phone mount, power bank, small cooler, quick-dry towels.
Nice-night outfits: Casual coastal dress or button-down for Savannah/Charleston/Nashville dinners.
Budget Snapshot (Couples, Mid-Range)
Lodging: $180–$350/night coastal & historic cores; mountains vary by season.
Activities: $25–$60 pp for boat tours/museums; free scenic walks abound.
Parking: $10–$30/day in historic districts; factor garages into lodging choice.
The video below is the trip across the St. John’s River on the Mayport Ferry – add a little fun on your road trip!
FAQs About Southern Road Trips
How many days do I need for this Southern United States road trip?
10 days is the sweet spot; add 1–2 extra days in Asheville and/or Chattanooga if you want slower mornings and hikes.
What’s the most romantic stop?
Tie: Savannah and Charleston for historic ambiance; Clearwater Beach for sunsets; Jekyll Island for quiet beaches and bikes
Is the mountain driving difficult between Charleston and Asheville?
It’s interstate most of the way with steady climbs; allow 4.5–5.5 hours and take scenic breaks.
Can I do this car-free?
Not easily. Rideshares work within each city, but the coastal-to-mountain hops are best with a car.
Best photo moments along the route?
Clearwater sunset at Pier 60, St. Augustine lighthouse, Driftwood Beach on Jekyll, Savannah’s Forsyth Park, Charleston’s Rainbow Row, Blue Ridge overlooks near Asheville, Nashville’s Ryman or a skyline river shot, Chattanooga’s Walnut Street Bridge.
What’s the order of beaches vs. mountains?
Start beach-side (Clearwater → St. Augustine → Jekyll → Savannah → Charleston), then up to Asheville and across Tennessee for music and river cities.
Vacation Planning Tools
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