• Janessa

Historic Southern Coast: Family Road Trip

Updated: Jun 28, 2019

When most people think of the South, I'd imagine they think of moss oak trees, fried chicken, soul food, and sweet tea, (I do at least) But, I wonder do they also think of cobblestone streets, horse-drawn carriages, enchanted alleyways, and historic architecture. Well, there are three Southern cities who have ALL of these things. St. Augustine, FL , Savannah, GA and Charleston, SC are each quintessentially Southern and each undeniably historic. They are located on the Southern Coast of the United States, just hours from each other, and each has so much to offer to the roadtrippin' family.

Of course, you could spend a week exploring each place but why not take that same week and see all three! You can explore each historic coastal city for two days plus add one day of driving and have such an amazing week-long family road trip!

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(1) St. Augustine, FL

St. Augustine holds the title as the oldest continuously occupied European settlement in the United States. It was established in 1565 by the Spaniards and of their presence and rule are everywhere. Take your family to visit Castillo de san Marcos aka "the fort" a coquina fortress built by the Spanish. Coquina, a stone composed of seashells and in Spanish means "tiny shell", plays a large part in St. Augustine's history and remnants can be found all around town, from walls, streets, and famous structures. It's a great living history lesson to teach your kiddos about this unique rock formation while giving them the opportunity to touch it and see for themselves how it has stood for hundreds of years. Talk about a strong foundation!

If you really want to learn all about St. Augustine's history, from Spanish founding, to British rule, and finally American territory and city, take a guided tour! You and your family should choose the tour right for you but we're such big fans of the trolley tour! Most trolley tours allow you to get on and off at various stops all while getting a much needed respite from that Florida heat (it is brutal, trust me!) I'd recommend the Old Town Trolley, with 23 stops and a free shuttle to the beach. The trolley tour will also take so much guesswork and planning out of your vacation, just hop on and you're sure to see the biggest attractions and sites. No Planning Needed!

my son had a blast on the Black Raven Pirate Adventure in St. Augustine!

St. Augustine like its cousins Savannah and Charleston also has a strong pirate history. Charleston probably has the strongest claim but each coastal town was known to have pirates grace their waters and streets. Please, I beg you, please take your little one to the Black Raven Pirate Adventure! I can't stop recommending this because it was one of the best vacation activities for our son. He still talks about it, his painted dolphin tattoo and saving the day. It's an interactive performance, yes, but you'll learn all about St. Augustine's pirate lore too. It's an expensive activity but so worth the price!

Of course, you'll want to walk St. George Street, eat ice cream at Kilwins, visit The Fountain of Youth, stop by the beach and eat at Columbia restaurant (No, it's not overrated) These are all the standard St. Augustine touristy things to do but they never get old to me and I'm pretty sure you'll love them too and have a great time in Old City!

I'll be writing a St. Augustine city travel guide and food guide soon, subscribe to stay up to date on the latest and learn more about this adorable historic coastal town.

Pictured below, left to right: (1) There is a strong pirate history in St. Augustine and other southern coastal cities. A guaranteed kid favorite, the Black Raven Pirate Ship Adventure live action show (2) The Fountain of Youth in St. Augustine, FL is a living history village dedicated to the Spanish explorers who came to Florida in search of the fountain of the youth. It is famous for the many peacocks who roam freely (3) The Old Town Trolley in St. Augustine is a great way to sight-see with your family


(2) Savannah, GA

Less than 3 hours north (or south) on I-95 from St. Augustine, FL, you'll come to the dreamiest little town that you ever did see. And, did you know all the gorgeous architecture that makes Savannah, well....Savannah, almost was wiped out! It survived fires, hurricanes, economic ruin, all to be almost demolished and built anew. No way, said a group of women who formed the Savannah Historic Foundation in the 1950s! Thanks to them, all the historic buildings were saved and we can walk all around this city (with an alcoholic beverage, even!) and get lost in its history. You think I would have learned this on a tour, nope, I learned all about Savannah's history from the owner of a vintage salvage shop called Two Women and A Warehouse! If you're into city art prints, up-turned furniture, and hip home decor, make a stop next time you're in town.

explore City Market during a self-guided walking tour of Savannah, GA

Savannah also has 24 historic squares, beautifully landscaped and maintained, perfect for long meandering walks. Walking is one of my favorite things to do in Savannah. You don't need to clog up your day, trying to get tour tickets, or see historic sites, or tasting specialty restaurants. Just choose a major boulevard (Bull Street, Abercorn Street, or Barnard Street) and walk until you dead-end at Forsyth Park. Don't worry, you'll see most of the important stuff along the way such as the Telfair Museum, City Market, The Cathedral of St. John the Baptist, and Juliette Gordon Low's birthplace (who is she? founder of the Girl Scouts). Walking the squares is also great with kids because they can take ample breaks, stretch their legs, and explore historic statues. Make sure to stop in Chippewa Square for a photo opportunity with the famous "Forrest Gump" bench.

Want to really win with the kiddos? Stand in line at the famous Leopold's Ice Cream parlor. Sometimes there is no wait, sometimes 10 minutes, other times 30 mins. You're saying to yourself, it's just ice cream! I know. It's the ice cream parlor's deeply entrenched history that sets it apart. It was was opened in 1919 and is still family-owned (and delicious!) with all the mom-and-pop charm Other family-friendly options include lunch at The Pirate's House, a little off-the-beaten-path but if your child is like my child, they'll think that upstairs gift shop may be the best thing about Savannah, GA (insert laughing face emoji) And, if you're the planning and organized type, why not pack a cooler of subs, fruits, and drinks and have the best little picnic in ForsythPark where you and your husband can lay together on a picnic blanket while your little one runs laps around you both! Super romantic (insert another laughing face emoji)

Pictured below, from left: (1) The Pirate's House in Savannah GA is a great restaurant for low country eats, fried anything and everything on the menu and don't forget the rum! (2) Forsyth Park in Savannah is over 30 acres with playgrounds, gardens, and so many moss oaks. It's such a great family-friendly destination in the city (3) The cathedral of St. John the Baptist is located off Abercorn Street near Lafayette Square, a place for quiet sightseeing. Make sure the kiddos are rested and well-fed and in a good mood.


(3) Charleston, SC

Did you know, no building in Charleston may stand taller than the tallest church steeple which is St. Matthew's Lutheran Church

Onward to Charleston, less than a 2 hour drive from Savannah city center to Charleston city center. You can't get better than that! Don't worry, more moss oaks here! Check them out in their full grandeur at Battery & White Point Gardens on the riverfront. Let your kiddo defend the city using the historic cannons in the park.

If you haven't already taken a carriage tour in one of the historic Southern cities, then book a horse-drawn carriage ride with Charleston's Old South Carriage Company. Our tour operator was absolutely brilliant, a young hip local that told the best jokes and shared the best local eateries.

In fact, Charleston is known across the nation for its restaurant scene famous for southern staples and low country cooking. Hello, carbs! Get ready to happily gain a pound or two. We had the BEST fried green tomatoes ever at Magnolias. And, the most delicious fatty southern, all-the-fixings breakfast at Hominy Grill (which is sadly closing its doors in 2019)

Before kiddos, we took a pub tour of Charleston and wanted to make sure to include the family-friendly options here with you because that's true love. We'd totally recommend the outdoor courtyard at the historic Blind Tiger Pub. And, order spuds and a Snake Bite, one of my all-time favorites half-guinness half-cider, at the kid-friendly Irish pub Tommy Condon's.

You'll want to walk off all that food and beer so walk along the water at Rainbow Row, google at the mansions, and then traverse the city until you reach City Market where you can pick up a souvenir or two or three.

If you have the time, make an hour long excursion to the long-standing Angel Oak, I promise it's not overrated and provides the best family photo opportunities.

Pictured below, left to right: (1) White Point Garden riverfront park in Charleston is filled with oak trees and large pedestrian boulevards, walk (or skip) here with your family (2) there are so many original cobblestone streets in Charleston, SC adding to the city's charm (3) Take a horse-drawn carriage tour of Charleston SC with your family


The Long Drive (With Kids): St. Augustine, FL to Charleston, SC

282 miles, 4 1/2 hours total driving time


Have any questions about this route? Comment below and I'll get back to you... Want more road trip itineraries? Subscribe to get my monthly newsletter with new travel guides, road trip itineraries, and journal entries from the road.

Many Blessings and Happy Travels,


We're the Martin family and we're in love with family road trips and family travel! We're currently renovating a 1974 Airstream Sovereign so we can continue our family road trippin' adventures across North America! We're hoping to inspire others to pack up and head out on the road! 


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