Friday: Arrival and Evening Stroll

3:00 PM – Arrive in Charleston and check into a charming boutique hotel like, The Restoration, Hotel Bennett, The Dewberry, Hotel Emeline or Zero George. 

5:00 PM – Take a leisurely stroll along King Street down to Broad St. to explore unique shops, galleries and the charming South of Broad homes. End at The Vendue for cocktails and sweeping views of the city at sunset.

7:30 PM – Enjoy dinner at Oak Steak House, The Establishment or Sorelle (walking distance from the Vendue). After dinner, take a twilight walk along Rainbow Row and The Battery to admire the historic homes and waterfront views or make your way up King St. for a nightcap at The Belmont.

Saturday: History, Culture, and Waterfront Charm

8:00 AM – Start your day with breakfast at Callie’s Hot Little Biscuit for warm, flaky biscuits topped with pimento cheese or fried chicken… OR for a tasty Southern brunch check out Miller’s All Day on King St.

9:30 AM – Head to Magnolia Plantation & Gardens to explore centuries-old gardens, wildlife, and historic grounds. Take a guided tour to dive into Charleston’s rich history.

12:30 PM – Return downtown for lunch at 167 Raw, located right on King Street, offering the best seafood in town.

2:00 PM – Spend the afternoon at the Charleston City Market, browsing handmade crafts, sweetgrass baskets, and local goods. Walk down to Joe Riley Waterfront Park to relax by the iconic Pineapple Fountain.

7:00 PM – Dine at Halls Chophouse, Stella’s for authentic Greek, or Indaco for Italian. 

8:00 PM – Indulge in famous coconut cake at Benne’s on Market St.

Sunday: Relaxation and Island Escape

8:30 AM – Take a morning stroll to Le Chambertin on Church St. for a French pastry before heading out to the beach.

9:30 AM – Drive to Sullivan’s Island (20 minutes from downtown) for a beach walk and fresh sea air. Stop by Fort Moultrie for a dose of Revolutionary War history.

11:30 AM – Brunch at The Obstinate Daughter, where coastal meets Mediterranean cuisine. Their shrimp and grits or wood-fired pizzas are crowd favorites.

1:00 PM – Return to Charleston for a final stroll through White Point Garden or browse the shops along King St. / Broad St (I recommend Boysterous Couture, The Little Market, Mildred Newberry, Seyahan Jewelry, Shop Harvest Moon Home, Sapphire Boutique, Candle Fish, Something About Me, etc.)

3:00 PM – Grab a parting scoop of gelato at Carmella’s Café & Dessert Bar before departing!