5-Day Itinerary for Savannah, Charleston & St Augustine

Solo Travel for Introverts Ratings

Sensory Peace – Super. Southern old towns are idyllic and embrace the slow life.

Solo-Friendliness – Medium. Many folks who visit here are local and generally a part of traditional families. However, recently, a lot of single travelers and tour groups are increasingly taking center stage.

Commute Friendly – Medium. There is no public transportation. However, renting a car is affordable and distances are relatively short, so you can go from town to town in an hour or two.

Predictability – High. Classic small-town American lifestyle. Do research on weather before going. as this place is prone to hurricanes. Some parts of the South have a reputation for racism, but I did not face any. Most locals are very welcoming of outsiders.

Safety – Medium. Most historic places have small-town safety higher than larger cities. But be careful of location of hotels, and avoid high-crime neighborhoods. However, this is easy to avoid by just comparing neighborhoods online.

Link for this – https://www.neighborhoodscout.com

Nerdy stuff –  Super. There is a plethora of museums, and nearly every historic house has been turned into one. There are castles with cannons, barracks, colonial outposts, civil war monuments, civil rights museums, pirate museums, prohibition history, plantation houses and the history of enslavement and emancipation.

Introduction to the American South-East

Colonial Map of Florida and Carolina
Colonial Map of Florida and Carolina

This region is filled with swamps and marshes allowing fishing, oyster-collecting and alligator-watching activities. There are criss-cross networks of oak trees covered in Spanish Moss, which dangles down the branches providing shade to entire plazas and squares.

The American South-East has a long history. Florida was a Spanish colony before Spain knew it was attached to a larger continent, and not an island. Georgia to its north was a British colony that came later and the two often fought fierce battles. Georgia and South Carolina fought the Civil War on the confederate side and has several military barracks, haunted mansions and plantations. There are landmarks of Civil Rights for racial equality and Cuban Immigration.

Southern Food has character and history, where food preparation is still homely and not lost to industrial manufacturing system. It’s currently making a comeback due to its emphasis on using all parts of meat, slow-cooked roux, gentle treatment of vegetables and flavors sharply contoured by spice.

Day -1-2 : Panhandle Florida

Jacksonville Florida is a good place to book a flight to and can be used as a base for Panhandle Florida as well as entry/exit point for the whole trip. You can rent a car from the airport for the whole journey and return it back before returning by flight.

Gateway Arch of Flagler College with Palm trees
Gateway Arch of Flagler College with Palm trees

St Augustine Old Town –

This is a cobblestone street-lined network of some of the oldest buildings in modern US, repurposed into museums, gift shops and restaurants, and comparable to Old towns in many smaller European cities. My favorite highlight is the  St Augustine Pirate & Treasure Museum – showcasing the real history of Pirates of the Carribean.

Cuban Style Spanish Villa with an Old Motor Car
Cuban Style Spanish Villa with an Old Motor Car

Castillo San Marcos –

This is a castle made by Spanish colonials to defend the town against pirates hired by Anglo-colonials to lay siege to Florida. If you come at the right time, there are period-actors demonstrating cannon blasts. The castle is made of Concha shells, that have sponge-like properties, meaning the more cannon balls you throw at them, the stronger they become from the squeeze of the ball making the walls more dense.

Charming Colonial houses of St Augustine

Swamp Tours –

Florida has amazing gator-filled swamps which can be toured on boats.


Day-3 : Georgia

Savannah –

Savannah Georgia is a beautiful city filled with Antebellum houses interspersed with shady gardens. It incorporates the Oglethrope city layout, which involves the houses in each square facing inwards towards gardens at the center, creating a wonderful sense of space and coziness while simultaneously embracing compact housing and walkability.

Apparently, the Union troops had initially planned to burn the city down like Atlanta, but they were so enthralled by its beauty, they decided to spare it, and present it to President Abraham Linclon for his birthday.

Colonial Red Brick buildings in Shopping Streets
Colonial Red Brick buildings in Shopping Streets

Some of the highlights of Savannah are the Prohibition Museum – which takes you through the history of liquor ban in the US and the effects it had on moral and political landscape, popular culture and crime syndicates. Several mansions are now museums, which can be visited. Some of them have been turned into restaurants, bars and boutiques.

Horse Carriage ride by an Antebellum house
Horse Carriage ride by an Antebellum house

Tybee Island –

For beach lovers.


Shady courtyards inside squares are popular in Southern cities

While driving between Georgia and South Carolina, I found myself outrunning a hurricane on the freeway. I had to pull over and check online for the path of the hurricane and route my car to go backwards, take a side exit and go all around it in a circle. Definitely check weather reports.

Day 4-5 : South Carolina

Alleyway leading up to a Church Steeple, Charleston
Alleyway leading up to a Church Steeple, Charleston

Charleston –

Charleston or Charles Town has the highest density of Church steeples in America, interspersed with Antebellum houses, colonial markets and military garrisons. Charleston is a very walkable city with narrow cobblestone streets and shady oaks giving you only hints of a steeple here, a veranda there, and a statue somewhere, hiding beautiful red-brick-lined townhouses, dockyards and warehouses.

Georgian era Cannons with gunpowder barrels
Georgian era Cannons with gunpowder barrels

I visited the Powder Magazine which had a history of gunpowder developed here along with British Imperial canons of various shapes and sizes. Another not-to-miss place is the several squares long Historic Charleston City Market which sells several local food specialties along with antiques and crafts.

Townhouse Museums in Charleston
Townhouse Museums in Charleston

Charleston Plantations –

This place is one of the few regions in the US producing rice and tea, as they require a humid climate and mild terrains. Some of the most beautiful plantations are worth a visit. It’s a good to ensure they acknowledge the history of slave labor and other human rights violations before visiting them – there are many who not only dignify laborers but also put in special efforts to find out their names and lifestyles. 



Southern Food –

Southern Food Restaurants are new in the South, and people often prefer their family’s secret recipes over an outside establishment. However, in recent years, Southern Food has boomed as the next exotic cuisine and several Michelin-Star restaurants are now introducing this characteristic American food to international patrons. A good recommendation is the Ye Olde Pink House.

Sweet Tea Stand
Sweet Tea Stand

My favorite food in Charleston were the Low Country Oysters harvested from marshes here, and Carolina She Crab soup – which is a chowder made with roe(eggs) of crabs and laced off with Sherry or Bourbon.

While the Sweet Tea is great, be warned, it is very sugary. No, I really mean it. It will make a Starbucks Cream-Latte and McFlurry look healthy.

Banana plant at a Florida Mansion

For Charleston and Savannah, because they are nearby, you can choose one of them as a base and do the other as a day-trip if you are short of time. These places are also some of the most haunted ones in the US, so Haunted Tours are a special experience to look into. I had come here on Halloween and based on the enthusiasm in the three towns, I can easily say it’s the best time to visit during the year.

Inspiration before you go –

Songs –

Lil Nas X – Old Town Road (https://www.youtube.com/watch?v=w2Ov5jzm3j8)

Darius Rucker – Straight to Hell (https://www.youtube.com/watch?v=Im5N-0ZNf14)

RaeLynn – Tailgate (https://www.youtube.com/watch?v=6kR1qOdHbxI)

Books to Read –

Where the Crawdads Sing by Delia Owens


Movies to Watch –

Gone with the Wind

(https://www.imdb.com/title/tt0031381/ )


  1. Great tour – there is a lot to do and see in this part of the U.S. Charleston SC is an exceptional city to visit.

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