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Weekend Worthy: Three Romantic Days in Charleston

  • Writer: Jenny B
    Jenny B
  • Oct 17
  • 3 min read

Where to stay, what to eat, and the must-do moments in the South’s most charming city


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If cobblestone streets, pastel mansions, and sweet tea under Spanish moss sound like your kind of weekend — Charleston is calling. This coastal gem blends Southern hospitality with historic beauty and a thriving culinary scene, making it the perfect long-weekend getaway for couples.

Here’s how to spend 3 unforgettable days soaking up the charm, flavor, and romance of Charleston.


🛏️ Where to Stay

Zero GeorgeTucked into a cluster of restored 19th-century carriage houses, Zero George is a boutique dream — all whitewashed porches, lush courtyards, and cozy, romantic touches. It’s elegant without being pretentious and just a short stroll from the best of downtown Charleston.

💡 Why it’s Weekend Worthy: You can sip a glass of wine on the veranda, borrow a hotel bike, and explore at your own pace — no Ubers required.

Alternative Option: The Quarters on King — modern, spacious suites with full kitchens and easy access to the city’s best shopping and restaurants.


🍽️ Where to Eat

Day 1 Dinner — Husk You’ll find elevated Southern cuisine in a beautifully restored mansion — think fried chicken perfected, shrimp and grits redefined, and a bourbon list that’ll impress any whiskey lover.

Day 2 Brunch — Poogan’s Porch Charleston brunch at its best: buttery biscuits, strong coffee, and the cozy charm of an old Victorian home.

Day 3 Morning — Clerks Coffee Company Before heading home, grab a latte and a pastry from this chic café inside the Emeline Hotel. It’s the perfect slow start before your travel day.

🥐 Bonus: Don’t leave without a stop at Callie’s Hot Little Biscuit for a handheld taste of the South.


🧭 What to Do


Day 1: Arrival & Sunset Stroll

  • Check in and unwind at your hotel.

  • Wander through the French Quarter and take those quintessential Rainbow Row photos.

  • Enjoy golden hour at The Battery — the water views and antebellum homes make a magical first evening.

Day 2: Explore & Indulge

  • Start your day with a carriage tour to get the lay of the land and learn about Charleston’s history.

  • Stroll the Charleston City Market and shop local artisans.

  • Spend the afternoon exploring King Street’s boutiques and art galleries.

  • Wrap the evening with rooftop cocktails at The Watch, followed by dinner at 167 Raw for oysters and champagne.

Day 3: Slow Morning & Southern Farewell

  • Take a scenic drive or Uber to Magnolia Plantation & Gardens — one of the most romantic spots in the Lowcountry.

  • Stroll under centuries-old oaks draped in moss, and let the weekend’s slower pace linger just a little longer.


💡 Pro Tip:

Book your dinner reservations early — Charleston’s dining scene is hot, and the best tables go fast.


❤️ Final Thought

Charleston feels like stepping into another era — one filled with charm, flavor, and Southern grace. Whether you’re sipping sweet tea on a veranda, sharing oysters by candlelight, or wandering through centuries of history, every corner of this city invites connection.


✨ Weekend Worthy is about turning your PTO days into lasting memories.

Ready to make Charleston your next escape? Let me plan your perfect 3-day getaway — complete with the right hotel, handpicked dining, and personalized touches you won’t find on Google.


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