The Best Charleston Weekend Itinerary
Charleston, South Carolina is a city steeped in history, charm, and exceptional cuisine. Whether you’re wandering about its cobblestone streets, admiring architecture, or indulging in its renowned culinary scene, Charleston offers a rich tapestry of experiences. These are just a few of the reasons why we selected Charleston, SC as the backdrop for our Fall 2024 campaign.
Fall is one of our favorite times to visit Charleston, as the temperatures have cooled, the crowds have thinned, and oysters are in season (say less!). We could spend weeks in the city, but if you have just a weekend to explore this southern gem, let us guide you through an unforgettable itinerary-featuring some of the city’s finest hotels and restaurants.
Day 1: Arriving in Charleston, SC
Morning: Checking In
Start your Charleston adventure by checking into one of the city’s luxurious hotels. Each offers a unique taste of Southern elegance.
The Dewberry is a modern classic, blending mid-century design with southern charm. Alternatively, The Restoration is an upscale, boutique option with a focus on comfort and local culture. For a touch of modern luxury, The Loutrel presents a stylish, relaxed atmosphere and has a spacious rooftop terrace where you can find dinner and 365-degree views of the city. Zero George Street Hotel offers a historic feel with contemporary touches. The Charleston Place and Hotel Bennett provide elevated sophistication and Southern hospitality, while The Vendue is perfect for art lovers. The Dunlin provides a relaxing oasis that is only a short drive from the city. We enjoyed our stay at the Palmetto Hotel for our campaign photoshoot.
After settling in, grab a sweater or pullover and head to The Daily for breakfast. This popular spot offers a delightful array of pastries, sandwiches, and coffee. For a different vibe, try Harken Cafe, known for its relaxed atmosphere and excellent breakfast fare. If you're in the mood for something unique, The Harbinger Cafe and Bakery serves up creative and delicious breakfast options.
Afternoon: Exploring and Lunch in downtown Charleston
Stroll through historic downtown Charleston, absorbing the city’s charm. For lunch, visit Rodney Scott’s BBQfor some of the best Southern BBQ in town. Alternatively, Felix offers a delightful range of sandwiches and salads in a chic setting. If you're craving something lighter, Brown Dog Deli is a casual spot with a fun atmosphere.
Evening: Dinner in Charleston
You can’t spend a weekend in Charleston without indulging in exquisite seafood. The coastal town is known for their low country shrimp and grits, fresh oysters, and she-crab soup. For a memorable dinner, put on your favorite men’s button-down or women’s classic top and head to Leon's Oyster Shop. This laid-back spot is renowned for its oysters and fried chicken. Another excellent option is The Darling Oyster Bar, offering fresh seafood in a vibrant atmosphere. 82 Queen also offers a sophisticated dining experience with a focus on fresh, local cuisine and is known for their shrimp & grits and she-crab soup. No matter which spot you choose, you’re in for a treat with Charleston’s seafood offerings - just remember to book your table well in advance to secure a spot! After dinner, take a boat tour of the Charleston harbor with Daniel Island Ferry and watch the sunset from the water.
Day 2: Southern Comfort and Coastal Views
Morning: Breakfast and Coffee
Start your day with breakfast at Holey City Bagels, a local favorite for its delicious bagels and coffee. Babas on Cannon, a European inspired café, offers lighter breakfast options of pastries and avocado toast, and is known for their whipped honey espresso latte.
Afternoon: Lunch and Relaxation
After breakfast, put on your favorite dress or men’s polo shirt and explore Charleston’s historic sites and shopping districts. For lunch, if you’re in the mood for something more casual, head to Island Cabana Bar.This local gem offers stunning water views and a relaxed vibe. For a unique dining experience with great views, The Obstinate Daughter on Sullivans Island is worth the short drive. Make sure to pack your favorite men’s swim trunks if weather permits because The Co-Op on Sullivans Island offers sandwiches and Frosé that are perfect to grab before spending the afternoon out on the beach.
Evening: Dinner
For dinner, consider Post House for its refined Southern dishes in a historic setting. If you’re in the mood for something a bit different, Tavern and Table offers a great atmosphere and diverse menu options. For a sophisticated dining experience, Slightly North of Broad (SNOB), serves elevated Southern cuisine in an elegant setting. Don’t forget to enjoy a cocktail - especially their great cosmopolitan or pineapple martini.Southbound, a spot with a relaxed, renovated Charleston house feel, is known for their live-fire cooking and menu that changes daily. After dinner, be sure to enjoy a cocktail at Citrus Club, a rooftop bar known for its citrus-inspired cocktails and incredible views of the sunset.
Day 3: Exploring the City’s Hidden Gems
Morning: Breakfast and Brunch
Begin your day with breakfast at Island Provisions or Sorelle Mercato if you’re craving a sweet treat. For brunch, try Basic Kitchen for a health-conscious menu featuring fresh, local ingredients.
Afternoon: Exploring
Explore the city's art galleries, historic landmarks, and quaint shops in the afternoon. If you’re in the mood for a bite while exploring, Virginia’s on King offers a lovely setting and delicious Southern fare. For a bit more adventure, take a trip to Kiawah Island where you can tee off at one of their seven renowned golf courses—our top pick is The Ocean Course. If golf isn’t your thing or if you are in the mood for some shopping, Freshfields Village is our favorite pick for the best mix of local shops and your favorite brands. We might be a bit biased, but the Southern Tide store there is a standout. When you’re ready for a break from shopping, head to 48 Wine Bar to enjoy a selection of wines through their automated wine stations.
Evening: Final Dinner
For your final evening in Charleston, put on a men’s navy blazer and your favorite preppy fall dress and enjoy a meal at The Ryder Cup Bar for a relaxed atmosphere and amazing oceanfront views. If you’re wanting to head back into downtown Charleson, venture to Melfi’s for a classic Italian dish. For something a bit more relaxed, Fleet Landing provides a great atmosphere and delectable dishes.
Packing List
Charleston, SC is known for its Southern charm and warm climate. Southern Tide offers stylish and comfortable clothing that fits perfectly with the city’s laid-back and coastal vibe. Here’s a Charleston packing list for both men and women that should keep you looking sharp while enjoying the city.
Men’s Charleston Packing List
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Men's Shirts for Charleston
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Button-Downs & Polos: Southern Tide Sport Shirts and Skipjack Polos are perfect for Charleston. They are lightweight and breathable, perfect for transitioning easily from day to night, and versatile for any activity.
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Men’s bottoms – best pants and shorts
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Varied Options:
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The brrr-die Short: Designed for ultimate comfort and style, these shorts feature a lightweight, breathable fabric that's perfect for warm Charleston days. With a sleek cut and versatile color options, they're a must-have for casual outings or weekend adventures.
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The Sullivan Five Pocket Pant: These pants combine classic style with modern functionality. With a tailored fit and five-pocket design, they offer both practicality and a polished look. Ideal for transitioning from day to night, they're perfect for everything from a stroll downtown to a dinner date.
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Men's Outerwear for a Weekend Trip
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Light Jacket or Sweater: Choose from performance vests, pullovers, or quarter-zips for comfort in the cooler fall weather.
Women’s Charleston Packing List
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Women's Dresses and Sets:
- Southern Tide Dresses and Sets: Ideal for Charleston’s fall weather, our classic maxi dress or matching maxi skirt and shirt set are perfect for Charleston. Whether you’re exploring the city or enjoying a casual meal, these versatile pieces offer both comfort and style for any Charleston outing.
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Women’s Bottoms – Best Women's Pants and Shorts
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Varied options:
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Maxi Skirts: Elegant and versatile, our maxi skirts are perfect for a range of occasions, offering both comfort and style in Charleston’s fall weather.
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Performance Pants: Engineered for activity and comfort, our performance pants are ideal for everything from casual outings to more active adventures.
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Women's Outerwear for a Weekend Trip
- Women’s classic sweaters and quilted pullovers: Timeless and versatile, these pieces provide both warmth and style, making them perfect for layering during cooler weather.
