Charleston, SC Local Itinerary

A Local’s Guide to Charleston, South Carolina:  Here is a list of Charleston Hidden Gems, by Rent.com. 

Charleston, SC—known for its historic homes, charming cobblestone streets, and world-renowned cuisine—offers more than just postcard-perfect views of the Battery and Rainbow Row. Whether you’re considering a move or just visiting for a weekend, here's how to experience Charleston like a local.

Where to Stay

When visiting Charleston, accommodations are more than just a place to rest your head; they set the tone for your entire stay. Here are a few standout options:

• The Dewberry: This luxury hotel perfectly blends mid-century modern design with Southern charm, offering a chic rooftop bar and a prime location near Marion Square.
• The Inns Airbnb: A collection of beautifully restored homes that offer the comfort of a hotel with the privacy and character of an Airbnb.
• Zero George: An intimate boutique hotel that serves up history, elegance, and a delightful culinary experience, with cooking classes to boot.
• 30-Day Rental on Sullivan’s Island: For a more extended stay, consider renting a beachside home on Sullivan’s Island—just 20 minutes from downtown, but it feels like a world away.

Daytime Adventures

Explore Downtown by Foot, Bike, or Rickshaw
Start your day with a stroll through the Historic District. King Street is Charleston’s shopping mecca, where you can discover local boutiques, antique shops, and art galleries. For a more scenic experience, rent a bike, golf cart, or take a rickshaw ride through the narrow, tree-lined streets, allowing you to admire the city’s iconic architecture at a leisurely pace.

Cocktail Hour Before Dinner
Begin every evening with cocktails at one of Charleston’s chic watering holes. Try a rooftop bar like The Citrus Club, which boasts panoramic views of the city, or the cozy and stylish Vintage Lounge. For a more intimate experience, Bar 167 offers a trendy setting perfect for pre-dinner drinks.

Dine in Style
Charleston’s food scene is legendary, and dinner here is not just a meal but an event. Some standout dining experiences include:

• Halls: 5-Star steakouhouse. 
• Melfi’s: An upscale Italian eatery with classic dishes in a modern setting.
• 167 Raw: A raw bar that serves up some of the best seafood in town, including fresh oysters and lobster rolls.
• Felix: A Parisian-inspired bistro known for its sophisticated yet approachable menu.
• Frannie & The Fox: A wood-fired eatery with a fun and lively vibe.
• Chubby Fish: An off-the-beaten-path seafood spot loved by locals, walk-ins only.
• 5Church: A unique dining experience in a converted church, featuring creative New American cuisine.

Evening Entertainment
After dinner, start the night off with a drink at Halls Chophouse, an iconic spot known for its warm Southern hospitality. From there, let the night take you wherever the mood strikes:

• The Cocktail Club, The Dispensary, or Blind Tiger: For live music in intimate settings.
• Republic: For DJ sets and dancing.
• AC's: A great place to unwind with a game of pool.
• The Commodore: An iconic spot for those wanting to dance the night away to live funk and soul music.

Weekend Wind-Down

Brunch Spots to Nurse Your Hangover
Nothing beats a leisurely brunch in Charleston. For an upscale experience, try Frannie & The Fox or The Post House. If you’re looking for something more casual, grab bagels at Island Provisions or swing by Prohibition for brunch classics in a lively setting.

Beach Day
No trip to Charleston is complete without a beach day. Head to Sullivan’s Island—Station 18.5 is a local favorite for its wide sandy shores and relaxed vibe. Enjoy a beachside lunch at The Longboard or pick up sandwiches from Mozzo or The Co-Op on your way in.

Sunset Cruise & Shem Creek
End the day with a sunset cocktail cruise around Charleston Harbor, taking in the breathtaking views of the city from the water. Companies like Charleston Classic Yachts and Palmetto Breeze offer memorable experiences. Afterward, head to Shem Creek for waterfront dining, where you can watch the dolphins play as you enjoy your meal.

Treat Yourself to a Spa Day

After a night of dancing, unwind at one of Charleston’s top spas. Whether it’s a massage at The Woodhouse Day Spa, a facial at The Charleston Place Spa, or a luxe treatment at The Dewberry Spa, you’ll leave feeling refreshed and ready to take on the city.

A Quick Trip to Kiawah Island

If you have time, make the 45-minute drive to Kiawah Island for afternoon appetizers and cocktails at The Sanctuary, overlooking one of the most beautiful golf courses in the South. Insider tip: tell the gate you’re going to “The Sanctuary for lunch,” and they’ll grant you access.

Cap Off Your Weekend with a Fancy Dinner

Wrap up your Charleston experience with a final dinner at one of the city’s top-tier restaurants. From the farm-to-table elegance of FIG to the upscale ambiance of High Cotton, there’s no shortage of incredible options.

Charleston has a way of capturing hearts with its undeniable charm, and after one weekend, you might just find yourself daydreaming about making this city your forever home. And if you do, I know a girl who can help make that dream a reality. One visit is all it takes to fall in love with Charleston—trust me, it happens!