There are countless ways to frame the relationship between Charleston and Savannah: sisters, rivals, bookends. In truth, the cultural capitals of the Lowcountry are perfect complements to one another, charming visitors with their deep history, irreverent edges and stunning beauty.
There’s simply no reason to see one when you can experience both—from live jazz in the Holy City to Savannah’s hush-hush speakeasy scene. Here’s a suggested itinerary for a weekend of exploration in Charleston and Savannah, featuring two unforgettable Select Registry properties.
12 p.m. Checking In.
Upon arrival in Charleston, 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 familiar ornament of Southern hospitality: “We’ve been expecting you.”
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 puts every Instagram-able sight and landmark within easy walking distance—from military monuments to the formidable estates that stand at attention on water’s edge.
Select Room: Karen recommends the Spell Room, the estate’s master suite with Two Meeting Street’s 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.
Husk may be one of Charleston’s hottest dinner reservations, but 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 scene, never more vibrant than 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 perhaps grab some cold-pressed iced coffee at Queen Street Grocery for walking around.
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. For rejuvenation after a day of touring, tea is a divine opportunity to recharge before a night on the town.
5:30 p.m. A stroll down 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 hundred-year oaks, 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. Across the harbor? Why, Fort Sumter, of course.
7 p.m. Rooftop cocktails, young-Charleston style.
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, stumble 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.
9:30 a.m. A full Southern breakfast at “home.”
Wake up to fresh 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.
Books (and Audiobooks): If you’re riding shotgun on your journey to Savannah, 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. There’s always the witty, atmospheric Midnight in the Garden of Good and Evil.
1 p.m. Checking in.
The Ballastone Inn staked its claim to Savannah as the Oglethorpe residence, changing hands until becoming a full-service inn in 1980. Its nineteenth-century charm is enthusiastically managed by innkeeper Jennifer Salandi. The Ballastone 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 tribute 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. A speakeasy scavenger hunt.
One of Savannah’s greatest secrets is the preponderance of hush-hush drinking establishments no guidebook will 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 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. Night cap 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 the inn.
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.