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Maybe you can relate, but road trips totally made a comeback for me when COVID hit. I knew that travel could still be done, it just was going to look different. This two week road trip that we ended up taking through the southeast US actually was in place of our two week Hawaii trip we had to postpone. This ended up being such a special trip and I’m here to spill the PERFECT southeast USA road trip itinerary!

One thing that made this road trip so amazing was that we had such a variety. Each city was so different from the one before it. We did small mountain towns, big cities, little beach towns, cities that exuded southern charm. I mean really, you won’t get bored with the scenery on this road trip

Where to go in the Southeast USA: the perfect 2 week road trip itinerary

Day 1: St. Simons and Jekyll Island

If you’re coming from Tampa, St. Simons Island is about a 4 ½ hour drive. It was the perfect distance for a pit stop and a great way to break up the drive. 

St. Simons and Jekyll Islands are both part of the Golden Isles, which make up Georgia’s coast between Jacksonville, Florida and Savannah, Georgia. They’re known for their marshes and beaches, and definitely a must stop. For a full itinerary for the islands check out this post!

TIP: You can start with whichever island you want to first, but we felt St. Simons was more of a daytime spot, while we wanted to enjoy Driftwood Beach and some of the restaurants on Jekyll Island around sunset. You will actually drive right past Jekyll Island to go to St. Simons Island, so the choice is up to you which order you want to visit them in!

Day 1- 4: Savannah, Georgia

After you’ve enjoyed your nice little day trip at the two islands, make your way to Savannah, Georgia. Just an hour and a half drive and you’re there and ready to call it a night! Or maybe you’re ready to rage. We definitely got settled in and went to bed so we could wake up refreshed and get off to an early start in one of my favorite cities.

Serving you southern food and charm, you won’t be able to get over how picturesque and interesting Savannah is. We visited when many restaurants and activities weren’t quite up and running yet, but we still found PLENTY to do.

Day 4-5: Charleston, South Carolina 

Cobblestone streets, pastel houses, and more of that southern charm can be expected as you make your way to Charleston. It’s a 3 ½ hour drive from Savannah, and a beautiful drive at that. 

Personally, I found Charleston to be beautiful, charming, and rich with history, but to be honest it wasn’t our favorite place. We initially planned on spending two days here, but decided to move on early. That being said, Charleston is some people’s favorite city! The beautiful thing about road trips is they are totally flexible! So, if you prefer, you can always do 2 days here and do fewer days in one of the cities later mentioned!

Check out my Charleston highlights here!

Days 5-7: Charlotte, North Carolina 

Once you’re ready to hit the road from Charleston, you’ll be embarking on a 3 hour drive over to Charlotte. Charlotte reminded me a lot of Tampa. Charlotte has this high energy cosmopolitan vibe. It’s known as a university town, but also a huge business and financial hub. Think rooftops, food halls, breweries, and speakeasies (see, just like Tampa!).

Views from rooftop in Charlotte, North Carolina
Pro Tip!: Use Spot Hero during your road trip to find cheap parking! I even use this when parking my car overnight so I don’t have to pay the hefty hotel parking fees!

Day 7-8 Boone, North Carolina

Boone is a stop that we added last minute since we left Charleston early, but wow am I glad we did! This small, charming mountain town will be one of your trip highlights! It sits right atop the beautiful Appalachian Mountains and is 20 minutes from Grandfather Mountain.

I recommend waking up early on day 8 so you can get to Grandfather Mountain when it opens. The hours vary depending on the season— check here for hours and rates for your visit! They are requiring tickets to be purchased online, so make sure to reserve your time slot.

Foggy morning on Mile High swinging bridge at Grandfather Mountain

Day 8-11 Asheville, North Carolina

The drives just keep getting easier and easier— in a short 1 ½ hour drive from Grandfather Mountain you’ll be in gorgeous Asheville! Nestled in the Blue Ridge Mountains of North Carolina, this gorgeous spot is known for housing the Biltmore Estate. Along with that, it also has an amazing art scene, fun breweries, and coffee shops, as well as exciting outdoor activities. For my Florida people, Asheville is like our St. Pete!

Here’s a full Asheville guide if you want more!

Day 11-12 Helen, Georgia

Leave Asheville at a decent time so you can make it to Helen by lunch! It’s just a 2 ½ hour drive, so as long as you hit the road by 10 am you should be good. If you can spend an extra day here, I recommend it.

Helen was one of our FAVORITE stops of the trip! You are going to absolutely fall in LOVE with this adorable Bavarian town! It will have you convinced you’ve left the country. For where to stay, what to do, and even what not to do on your Helen, Georgia adventures click here!

Day 12-14 Chattanooga, Tennessee

Once you leave Helen, you’re off to your last stop of the road trip! After a 2 ½ hour drive you’ll be in Chattanooga, Tennessee. Chattanooga isn’t named the scenic city for nothing. You are going to be surrounded with beautiful natural attractions and amazing hiking trails. But, don’t worry, if you’re a little beat after your previous road trip stops you’ll also be able to find plenty of leisure activities and lots of great food!

Want to know where to stay, eat, and play in Chattanooga? Check out this post for your perfect weekend in Chattanooga!

When is the best time to go on a southeast USA road trip

If you go between March and May you will be able to get nice weather as well as avoid the crowds. We went in the fall, and I would highly recommend going then. August-September the weather is starting to cool off, and kids are back in school so you can still potentially avoid some of the crowding you may experience if you visit in the summer.

We also did a lot of water activities like the Blue Hole (in Chattanooga), and tubing the Chattahoochee River (in Helen), and I feel like the water and weather temps were perfect for those activities to be enjoyable. 

Helen also has a pretty big Oktoberfest annually that they celebrate in September if you want to plan your trip around that!

drinking a beer at King Ludwigs in Helen Georgia

Have you ever done a big road trip like this? Let me know in the comments! 

Not sure what to pack up the car with on your 2-week road trip? Check out my ultimate road trip packing list! And be sure to check out my Insta @guidedbydestiny for more road trip adventures and Florida content!

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  1. What a beautiful road trip! I live in the UK but dream of doing a US road trip one day! This itinerary looks incredible! I especially like the look of Helen, what a beautiful place! I hope I get a chance to visit. Thanks for the great guide!

  2. This Southeast USA road trip guide is incredibly helpful. You’ve really thought through everything you need to know before planning a trip. Thank you for this helpful resource. Saving this guide for later!

  3. We hit North Carolina last fall in October and loved the Fall foliage. Yet, now that I have seen your post, I need to go back to visit Helen and then plan to spend time in South Carolina. Beautiful pictures.

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