Ultimate 5-Day Charleston Exploration Itinerary Itinerary

Enjoy a classic Southern breakfast at Magnolias, known for its hospitality and traditional dishes. Afterward, embark on a journey to the stunning Magnolia Plantation and Gardens, where you'll be surrounded by lush landscapes and rich history.

Have a casual lunch at The Obstinate Daughter on Sullivan's Island, known for its wood-fired pizzas and pastas. Spend your afternoon relaxing on the beautiful Charleston Daytime or Sunset Historic Harbor Cruise, taking in the scenic views and learning about the city's maritime history.

Dine at Fleet Landing Restaurant & Bar, a waterfront eatery with a menu featuring fresh seafood. Conclude your day with a Charleston Small-Group Ghost Walking Tour at Night, exploring the city's haunted past.

Start with a delicious breakfast at The Darling Oyster Bar, offering a selection of fresh oysters. Then, visit the elegant Aiken-Rhett House, where you can step back in time and explore one of the best-preserved townhouse complexes in the nation.

Enjoy a guided Charleston Historic Downtown Food Tour with Tastings, sampling the city's culinary delights while learning about its history. For a late lunch, head to Butcher & Bee for their creative sandwiches and mezze plates.

Dine at FIG, known for its seasonal cuisine and vibrant atmosphere. Afterward, take a leisurely stroll through the historic Circular Congregational Church and the serene Charleston Waterfront Park.

Enjoy a hearty breakfast at Poogan's Porch, a charming restaurant housed in a Victorian home. Fuel up for a day of exploration before visiting the Charleston Museum, where you can immerse yourself in the history and culture of the South.

For lunch, indulge in the Southern flavors at Husk, known for its innovative take on traditional dishes. Afterward, take a guided tour of the Joseph Manigault House, an exquisite example of antebellum architecture.

Dine at Leon's Oyster Shop, a laid-back spot with a menu featuring Southern classics and, of course, oysters. End your day with a Boos and Booze Haunted Pub Crawl Walking Tour, exploring Charleston's spookiest haunts while enjoying libations.

Have a delightful breakfast at 167 Raw, known for its fresh seafood and oyster bar. Then, visit the historic Fort Sumter Entry Ticket with Roundtrip Ferry, where the first shots of the Civil War were fired.

Enjoy a scenic lunch at High Cotton Charleston, offering a menu of elevated Southern cuisine. Spend your afternoon exploring the interactive exhibits at the Patriots Point Naval & Maritime Museum, home to the USS Yorktown and other historic vessels.

Dine at The Ordinary, a seafood hall and oyster bar set in a beautifully restored bank building. Conclude your Charleston journey with a relaxing Schooner Sailing Harbor Tour & Dolphin Watch, taking in the coastal breezes and spotting playful dolphins.