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)
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Clearwater Beach → St. Augustine: 200–230 miles • 3.5–4.5 hrs
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St. Augustine → Jekyll Island, GA: 80–100 miles • 1.5–2 hrs
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Jekyll Island → Savannah, GA: 90–100 miles • ~2 hrs
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Savannah → Charleston, SC: ~110 miles • ~2 hrs
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Charleston → Asheville, NC: 260–270 miles • 4.5–5.5 hrs (mountain driving)
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Asheville → Knoxville, TN: 115–130 miles • 2–2.5 hrs
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Knoxville → Nashville, TN: 180–200 miles • 2.5–3 hrs
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Nashville → Chattanooga, TN: 130–140 miles
Day 1 & 2: Clearwater Beach, Florida (Gulf Coast Kickoff)
Wide pure white sand beaches is what Clearwater Beach is known for.
- 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.
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