Southeast Road Trip Itinerary: Explore the Old South

Southeast road trip itinerary overview 

Virginia’s Historic Triangle: 4 nights 

We’re going to start the road trip in Virginia’s Historic Triangle. It includes three important towns (Williamsburg, Jamestown, and Yorktown), all within 20 – 25 miles of each other. 

With four nights here, you can spend one full day each in Jamestown and Yorktown and then have two full days to explore Colonial Williamsburg.

Charleston, South Carolina: 3 nights 

From Southeast Virginia, you’ll drive through North Carolina to the coast of South Carolina to spend a few days in that state’s top travel destination: Charleston. You’ll love exploring Charleston’s history and food. 

Savannah, Georgia: 3 nights 

Savannah, Georgia, is an absolute gem that must be seen by anyone who wants to travel the Southeast United States. With three nights here, you’ll be able to cover a lot of ground. And eat a lot of amazing food. 

St. Augustine, Florida: 3 nights 

From Savannah, you’ll head into Northeast Florida to explore the oldest city in the United States: St. Augustine, Florida. With its Spanish heritage, it will be a change from the English colonial influences in the other destinations on this itinerary. 

TRAVEL TIP: If you have flexible travel dates, you need to check out Going (formerly Scott’s Cheap Flights). You get amazing flight deals sent straight to your inbox with instructions on how to book directly with the airlines. Check out Going here. Going is my favorite way to find great travel deals. 

Start your Southeast road trip in Virginia’s Historic Triangle 

Unlike the other stops on this road trip, the Historic Triangle is three destinations in one. You’ll have time to explore three important cities in early American history: Williamsburg, Jamestown, and Yorktown. 

Jamestown, founded in 1607, was the site of the first permanent English settlement in the New World. Williamsburg, Virginia, home of the Colonial Williamsburg living history museum (the largest in the world), was the original capital of the Virginia colony. Yorktown was the site of the last major battle of the American Revolution. 

Where to stay in the Historic Triangle 

For the most immersive Colonial Williamsburg experience, stay at the Williamsburg Inn just steps away from Duke of Gloucester Street (Colonial Williamsburg’s “main street” through the Historic Center). 

We loved our stay at the Residence Inn Williamsburg. It’s just a short drive from the Colonial Williamsburg Visitor’s Center and offers a free breakfast.

What to do at the Historic Triangle 

I recommend you cover the major sites of the Historic Triangle in chronological order. 

1. Spend one full day exploring Jamestown, including visits to Jamestown Settlement and Historic Jamestowne. See my post about visiting Jamestown for all of the details and our best tips. 

2. Spend two full days at Colonial Williamsburg to get the most out of everything they have to offer. You won’t be able to see everything, of course, but you can do quite a lot in two days. Read my post about everything your Colonial Williamsburg itinerary needs to include so you don’t miss the top sites. 

3. Spend one full day in Yorktown. This will give you enough time to see the Museum of the American Revolution in the morning and then do the self-driving tour of the battlefield in the afternoon. And don’t miss my key tips for visiting Yorktown. 

Where to eat in the Historic Triangle 

There are a lot of great places to eat in the Colonial Williamsburg area. Our top picks include: 

• Food for Thought: our top pick outside the immediate Colonial Williamsburg Historic Area 
• Blue Talon Bistro: French bistro comfort food (reservations highly recommended) 
• Christiana Campbell’s: one of Colonial Williamsburg’s historic taverns (a must-do experience)

Move on to Charleston, South Carolina 

From Southeast Virginia, you’ll drive about 7 hours to Charleston, South Carolina, and stay for three nights (two full days). Charleston is the largest city in South Carolina and one of the top travel destinations in the Southeastern United States. 

Charleston was established in 1670 as Charles Town and named for King Charles II. It didn’t become Charleston until 1783. 

Where to stay in Charleston 

Things to do in Charleston, South Carolina 

Charleston is full of amazing things to do. Far more than you can do in just a short visit. Our top recommendations are below. For more details about these sites, make sure to read our Charleston itinerary post. 

• Aiken-Rhett House—painstakingly preserved antebellum Charleston townhouse with an outstanding audio tour (one of my personal “must-do’s”).
• Historic Charleston City Market—this four-block market featuring local artisans is considered by many to be a “must-do” in Charleston. 
• Waterfront Park—a wonderful park on the water that’s home to the famous Charleston Pineapple Fountain. 
• Fort Sumter National Monument—take a boat out to Fort Sumter and learn about the history of the military fort that was the site of the launching of the Civil War.
• Angel Oak Tree—(skip if short on time) take a short detour outside Charleston to see the immense tree believed to be the oldest living thing east of the Mississippi River. 

Where to eat in Charleston 

The food scene in Charleston is not to be missed. We highly recommend: 

• Fleet Landing—enjoy a delicious meal with great service right on the water. We loved their hushpuppies.
• Carmella’s Dessert Bar—a perfect stop for a coffee or a sweet treat near the Charleston City Market. Hubby loves their ice cream, and I really enjoyed the iced coffee I ordered.

If you decide to stay in Mount Pleasant outside Charleston to save some money on your hotel stay, then you’ll be close to some great breakfast places that we love.  

• Vicious Biscuit—amazing biscuits (Hubby gives their gluten-free options an enthusiastic thumbs up!). 
• Page’s Okra Grill—delicious breakfast standards like steak and eggs, French toast, pancakes, etc. 

The best things to do between Charleston and Savannah.

Explore stunning Savannah, Georgia 

From Charleston, South Carolina, it’s just a little over two hours by car to the next stop on the Southeast road trip itinerary: Savannah, on the east coast of Georgia. 

Savannah is known for its 22 squares that make little neighborhoods throughout the historic district, as well as its odd and often creepy history. Locals will be anxious to tell you that Savannah is the most haunted city in America.

It’s a perfect place to try a ghost tour. 

Explore more of the area with these ideas for weekend trips from Savannah.

Where to stay in Savannah 

We enjoyed our stay at the Marriott Savannah Riverfront. You can’t beat the location (right at the end of the historic River Street!) and mere steps from the famous Waving Girl statue.

If that doesn’t appeal to you, here are a couple of other options:

• Best for an Historic Inn: The Eliza Thompson House is an inn rich in history that’s situated near Forsyth Park and its well-known fountain.
• Best for Affordability: Holiday Inn Express Savannah – Historic District offers comfortable and affordable rooms just a short walk from historic River Street.

What to do in Savannah 

Savannah is a great place to spend a couple of days. I recommend you definitely get an early start on your first day and then do a history walking tour. We loved our tour with Genteel & Bard. For more details, see our Savannah itinerary post. 

Other popular things to do in Savannah include: 

• Stroll historic River Street—This historic street runs along the Savannah River and is home to hotels, shops, and restaurants in the downtown area.
• Check out the Waving Girl Statue—At the end of River Street is the famous Waving Girl Statue. Make sure to pay a visit. 
• Visit Forsyth Park—The famous fountain is a well-known photo spot in beautiful Forsyth Park. 
• Explore some of the 22 squares—Savannah’s founder laid out the old city in a grid with many small green spaces called squares. This created smaller neighborhood areas that have helped Savannah maintain the feel of a much smaller city than it is. 
• Eat lots of food—Savannah is a foodie traveler’s paradise. Check out our recommendations below.
• Tour historic homes — there are some famous homes, historic buildings, and historic sites in Savannah that you might want to check out, such as Mercer-Williams House.
• Visit Tybee Island (optional) — it’s one of Georgia’s barrier islands and one of the most popular day trips from Savannah. 

Where to eat in Savannah 

The food in Savannah, Georgia, is simply amazing. You could go there only for the food and leave happy. We’ve listed a few of our favorites here, or put yourself in the hands of an expert and take a guided food tour of Savannah’s amazing cuisine.  

• Vic’s on the River—delicious food and outstanding service with great views of the Savannah River. Perfect for a special occasion dinner. 
• The Collins Quarter—awesome breakfast in a wonderful atmosphere. Large portions. Don’t miss their lavender mocha.
• Leopold’s—iconic ice cream spot. Famous for their Tutti Frutti flavor.

Interested in just seeing Charleston and Savannah? Check out my Charleston and Savannah itinerary.

End your journey in St. Augustine, Florida 

From Savannah, Georgia, continue the Southeast road trip to Florida. You’ll head south and drive a little over three hours to St. Augustine. St. Augustine is the oldest city in America and was founded in 1565 by the Spanish. It’s a fun city full of rich history and culture. And some great places to eat. 

It’s a great place to wrap up a road trip. You could also start this road trip itinerary in St. Augustine and work your way north to Virginia. 

Where to stay in St. Augustine 

A vacation rental just steps from the historic district, like this one on Airbnb has plenty of room for a small family, or it’s perfect for a couple. And since it includes a full kitchen, it’s easy to save money on food. 

If you’re interested in hotel accommodations, here are some top-rated options: 

Best for Spa Romance: Casa Monica Resort & Spa

Best for Walkability: The Penny Farthing Inn bed & breakfast is just steps from the popular Lightner Museum.

Great Value: Hampton Inn St. Augustine Downtown Historic District

What to do in St. Augustine 

St. Augustine is full of fun things to do, and the historic center is so nicely compact that it’s easy to get around easily from one site to another.

For more information about these sites, make sure to read my St. Augustine itinerary post. 

• Castillo de San Marcos National Monument—old Spanish fortress built out of coquina stone and managed by the National Park Service (a must-see). 
• Fountain of Youth Archeological Park—original site of St. Augustine and the Timucua village Seloy. 
• Colonial Quarter—This living history museum is much smaller than Colonial Williamsburg, but the tour includes some interesting history of the Spanish in St. Augustine. 
• Pirate & Treasure Museum—fun and engaging exhibits about the history of piracy in the area and some interesting historical artifacts. 
• Concert at the St. Augustine Amphitheater (optional)—if you have time and the venue’s event calendar aligns with your trip, consider buying tickets to a show at The Amp. It’s a lot of fun. 

Where to eat in St. Augustine 

St. Augustine has some great dining options. Here are our top picks for lunch or dinner (reservations recommended): 

• The Floridian: Popular local eatery with great food and service. Excellent vegetarian and gluten-free options. This was my favorite dinner of our stay in St. Augustine.
• Columbia: Large menu with some great gluten-free options and a few solid vegetarian options. Hubby exclaimed Columbia has the best flan he’s ever tasted. 

For a sweet treat or afternoon snack, we recommend: 

• The Hyppo Gourmet Ice Pops: loved these gourmet popsicles in a ton of fun flavors.  
• Cousteau’s Waffle and Milkshake Bar: We loved these awesome dessert Belgian waffles and handspun milkshakes. Makes a substantial snack for sure! 
• Mayday Ice Cream: delicious ice cream! They even have dairy-free options. 

The bottom line

The Southeastern United States is so full of culture, history, and fun things to do that you’ll be dying to go back once you get a taste of it. 

We thoroughly enjoy seeing early American settlements and how they have been preserved today to make sure that their important history lives on. So, hop in your car (or a rental) and journey through the Old South. You’ll learn a lot about the history of the area and experience some amazing food along the way.