Charleston Battery

A Tale of Two Cities: The Best Savannah to Charleston Road Trip

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Road Trips

There are countless ways to frame the relationship between Charleston and Savannah: sister cities, rivals, bookends. From live jazz in the Holy City to Savannah’s hush-hush speakeasy scene, our guide to the best Savannah to Charleston road trip features the best suggestions to include in your itinerary! If you’re traveling with your sweetheart, be sure to check out our Romantic Getaway Guide for tips on how to make your trip extra special!

A Savannah to Charleston Road Trip in 48 Hours

In truth, these cultural capitals of the Lowcountry perfectly complement one another, charming visitors with their rich histories, irreverent edges, and stunning beauty. There’s simply no reason to see just one when you can easily experience both!

Day One: In Charleston

12 p.m. Check-in at Two Meeting Street Inn

Upon arrival in Charleston, South Carolina, travel South of Broad to your first destination: Two Meeting Street Inn. Owner and innkeeper Karen Spell Shaw often greets guests at the door with that sweet, Southern hospitality.

Two Meeting Street has been owned and operated by the Spell family for three generations and boasts one of America’s most-photographed porches, tucked behind gated front gardens. Its location in the heart of Charleston’s Battery District and is within easy walking distance of every Instagram-able sight and landmark.

Select Room: Karen recommends the Spell Room, the estate’s master suite featuring show-stopping architectural details: a turret and private porch. Throughout the inn, you’ll find classic Southern décor, oozing with charm and timeless elegance, as well as meaningful family touches.

1 p.m. Lunch on Queen Street

While Husk is one of Charleston’s hottest dinner experiences, give it a try for lunch. Dig into signature pimento cheese (Lowcountry pâté) and honey-glazed quail. Next door to their main dining room is an innovative, freestanding tavern, where craft cocktails reign supreme.

2 p.m. An Artsy Promenade

Charleston is home to a robust art and cultural scene, never more vibrant than during the Spoleto Festival in early summer. The Spell family recommends Anglin Smith, the Robert Lange Studio, and the Martin Gallery, located at the corner of State and Broad. Peruse exhibitions and then grab a cold-pressed, iced coffee at Queen Street Grocery while strolling along cobblestone streets.

4:30 p.m. Lowcountry Tea on Meeting Street

Each day, Two Meeting Street serves afternoon tea with Lowcountry classics like lime pound cake and traditional Charleston shrimp paste. Take in the relaxing, quintessentially Southern porch and mingle with guests from all over.

5:30 p.m. Stroll Along the Battery

Early evening is the perfect time to explore the Battery, with its imposing facades and colorful architecture along Rainbow Row. You can’t miss the ancient oak trees, dangling Spanish moss, magnolia and Resurrection ferns. As Karen says, “When you’re here, you know you’re in Charleston.” Take a photo near the pyramid-stacked cannonballs and admire the topiaries. You can even catch a glimpse of Fort Sumter across the harbor.

7 p.m. Rooftop Cocktails

Perched atop the Grand Bohemian Hotel, Élevé unfurls sweeping city views and vibrant exterior design. You’ll find something for everyone on their extensive wine list.

8 p.m. Dinner at FIG

FIG is a haven for food-lovers, evident in their Beard-winning approach to fresh, delectable ingredients. Highlights include their tartare of snapper and olive, slow roasted black bass and sautéed soft shell crab. Local seafood is the star. For a more casual atmosphere, Chef Mike Lata also created The Ordinary on Upper King.

10 p.m. Prohibition-Era Live Jazz

Over on King Street, step into the Charleston Grill for a live jazz trio every night. Whether you’re just starting the party with a flavorful champagne cocktail or capping the night with a single-malt scotch, music and ambiance abound. This charming establishment sets the scene for a romantic experience unlike any other.

9:30 a.m. A Full Southern Breakfast at “Home”

Wake up to freshly brewed coffee served with a view from the piazza of White Point Gardens and the river beyond. The daily hot Southern breakfast, (which never fails to tickle guests’ taste buds) includes dishes like Lowcountry crab quiche, pimento cheese grits, creme brulee French toast and more delicious favorites. As you bid Charleston farewell, take some parting glances at the splendid Battery.

Additional Select Registry Properties in Charleston

John Rutledge House Inn Bed & Breakfast

Consider staying on Broad Street at one of the most unique, historic buildings on the peninsula. John Rutledge built the John Rutledge House Inn Bed & Breakfast in 1763 and it still stands to this day as one of the many stunning antebellum architectural feats of the Holy City. This home is a National Historic Landmark and is on the National Register of Historic Places. Some rooms have elaborately carved Italian marble fireplaces, and original parquet flooring while others feature 18th-century reproduction furniture and original plaster molding. 

Hit the Road

Familiarize yourself with some of the local Lowcountry legends in literature and listen to an audiobook during your road trip. Consider the iconic works of Pat Conroy. For a kinder, gentler approach to the Lowcountry, try All Summer Long by Dorothea Benton Frank. And to prepare you for Savannah, select The Bee and the Acorn—a memoir by Paula Susan Wallace, founder of the Savannah College of Art and Design. Or, there’s always the witty, atmospheric Midnight in the Garden of Good and Evil.

Day Two: Savannah

1 p.m. Check-in at The Ballastone Inn

The Ballastone Inn staked its claim to Savannah, Georgia, as the Oglethorpe residence, changing hands until becoming a full-service inn in 1980. Innkeeper Jennifer Salandi enthusiastically manages its nineteenth-century charm. The inn is located in the heart of Savannah’s historic district, between Wright Square and Chippewa Square—an ideal home base for your exploration. Around the neighborhood, stroll the famed Squares of Savannah.

There are 24 total—each more beautiful and richly landscaped than the last. Each February, downtown comes alive for the Savannah Book Festival, featuring more than 40 authors and 10,000 attendees. Past keynote speakers include Stephen King, Anne Rice, Al Gore, and Dana Perino.

Select Room: Scarlett’s Retreat and Rhett’s Retreat are styled in soft, feminine and oaky, masculine tributes to their namesake characters in Gone with the Wind. With such personality across room options, it’s a choose-your-own-adventure of moods and aesthetics.

2 p.m. Embark on a Speakeasy Scavenger Hunt

One of Savannah’s greatest secrets is the preponderance of hush-hush drinking establishments that no guidebook can show you. If you ask around the historic district, you might find a keyholder to Mata Hari, a mysterious watering hole rated among the best in Savannah. Visitors must possess a key or enter with a keyholder, so porters, waiters, and concierge around town might lend clues for gaining access to the historic gin joint. South Magazine describes it as a “gentleman’s study” with titillating burlesque shows.

4 p.m. Tea at the Inn

The Southern tradition of afternoon tea keeps rolling in Savannah, and the Ballastone takes it very seriously with silver, scones and tea sandwiches. You’ll get a chance to meet and socialize with fellow guests before retiring to your room. You’ll notice that wine and beer are served all day at the Ballastone. Take it easy—there’s a full night ahead.

6 p.m. Hors d’oeuvres in the Courtyard

Not to be outdone by tea, the Ballastone Inn hosts daily appetizers for guests to enjoy before a night on the town. Inventive crostini and more conversation create a launch pad for adventures after dark.

6:30 p.m. Dinner at the Olde Pink House

This Savannah classic has a chilled seafood platter that visitors can’t miss. After this meal, you’ll understand why Savannah is called the Hostess City of the South. Jazz in the basement—still?

8 p.m. Entertainment at the Savannah Repertory Theater

One of Savannah’s greatest assets is the Repertory Theater, staffed with local artists who mount productions year-round. Provocative material like Vampire Lesbians of Sodom can get the blood pumping while more traditional fare like The Robber Bridegroom is a Lowcountry fairytale by the Pulitzer-winning author of Driving Miss Daisy. Take your seats and enjoy a night of culture. A schedule is available here.

10:30 p.m. Nightcap at Mata Hari

Assuming your intrepid scavenger hunt paid off, you’ll have a key (or a keyholder) to Savannah’s most exclusive, mysterious club. Local lore says there are others—get behind the velvet curtain and a new, top-secret world of decadence and ribaldry opens to you in Savannah. If you’ve failed to gain entry to a covert speakeasy, there are plenty of other local bars to check out after the theater. Try 22 Square Bar at the Andaz Hotel or Perch at Local 11 Ten.

9 a.m. Breakfast at Ballastone

At the Ballastone, breakfast specialties include a complete continental bar with fresh breads, yogurt, homemade granola, fresh fruit, and steel cut oatmeal—as well as chef’s specials prepared with seasonal ingredients. After a late night in Savannah, the leisurely 8-10 window will give you plenty of time to unwind before your departure.

Additional Select Registry Properties in Savannah

Azalea Inn & Villas

Situated in a quiet residential area of Savannah’s famed Historic District lies the Azalea Inn & Villas. When you stay here, you’ll be within walking distance of some of Southeast’s most notable landmarks and Georgia’s treasured jewels. The owners pride themselves in being environmentally conscious. They have an installed micro-drip irrigation throughout the property, and they also have a vegetable garden in which they grow fresh ingredients used in their cooking.  

Stay Select

Make the most of your Savannah to Charleston road trip (or any vacation) when you choose to stay in a Select Registry bed and breakfast, inn, or boutique hotel. Our quality-assured properties exceed expectations and set new standards in lodging. Center your stay around spas and relaxation. Seek out accommodations near natural wonders or outdoor adventures. Regardless of whatever type of experience you’re hoping to have, rest assured that when you choose to Stay Select, you’re choosing the best of the best.

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