Suggested Itinerary

📍Day 1: Classic Charleston

Kick off your Charleston adventure with coffee and donuts from Brown’s Court Bakery— a cozy neighborhood favorite set in a historic house.

Next, dive into the city's rich past with a guided walking tour of the Historic District, where you’ll pass antebellum mansions, hidden gardens, and centuries-old churches. Be sure to stroll along the Battery for sweeping waterfront views and stories from Charleston’s storied past.

Spend the afternoon exploring the boutiques and galleries of King Street, followed by a stop at the iconic Rainbow Row. Then head south to wander the oak-lined streets of South of Broad, one of the most picturesque neighborhoods in the South.

For lunch, grab a table at Basic Kitchen - bright, buzzy, and health-forward, it’s perfect for a midday pick-me-up.

In the evening, enjoy fried chicken, oysters, and frosé at the ever-popular Leon’s Oyster Shop. After dinner, stroll through the Charleston City Market—a buzzing stretch of local vendors and handmade goods or over to The Commodore—an upbeat lounge with live music, vintage vibes, and a welcoming crowd.

Or, check out Trio Nightclub for a full on club experience with dancing and EDM-style DJ shows.

💡 High Low Tip: Want to go deeper than the standard history spiel? I can pair you with a private guide who tailors the tour to your interests—architecture, Black history, ghost lore, or all of the above.

🦐 Day 2: On the Water and Local Culture

Kick things off with coffee and a breakfast sandwich at Clerks Coffee Co., a sleek café that also turns into a wine bar later if you want to circle back.

🚤 Next up: head to Shem Creek for a paddleboard or kayak session. It’s an easy, scenic launch with the potential of a dolphin sighting. It’s busiest after lunch, so go paddling earlier for calmer water and better wildlife spotting (yes, dolphin sightings are legit).

Lunch with a view? Grab a table at Saltwater Cowboys or Tavern & Table, both serve local seafood, Southern staples, and cold drinks right on the water.

Back in town, check out the art scene:

• Halsey Institute of Contemporary Art – small, edgy, and free

• Gibbes Museum of Art – classic Charleston with rotating exhibits
  

Wrap up your day with sunset drinks at The Watch Rooftop —great views, great cocktails. Suggested dinner spot is FIG, a local favorite known for seasonal, farm-to-table dishes.

If you’re still up for more, stop by The Commodore for live music or sneak into Faculty Lounge (yes, there’s a door code).

💡 High Low Tip: Prefer a private guide? I’ll set you up with a local outfitter who knows the waterways and galleries.

🎨 Day 3: Culture & Chill

Ease into your day with coffee and a pastry at Harken Café—tiny, cozy, and full of charm. Or swing by Kudu Coffee & Craft Beer if you want a laid-back patio vibe and the option to switch from espresso to beer without skipping a beat.

Spend your morning exploring the local art scene:

• Gibbes Museum of Art (if you didn’t make it yesterday)

• Redux Contemporary Art Center – edgier, rotating exhibits by working artists
  

Hungry? Head to Xiao Bao Biscuit for bold Asian comfort food in a funky former gas station. The cabbage pancake is a must.

After lunch, your afternoon is flexible:
• Take a ferry ride to Fort Sumter for a bit of history and harbor views
• Or chill under the mossy oaks at White Point Garden—great for a walk or people-watching

For your final dinner, you’ve got options:

• Husk Charleston for modern Southern fare in a historic house

• Halls Chophouse if you’re in the mood to go all-in on steak and service

• Rodney Scott’s BBQ if you’d rather end the trip with a plate of legendary whole-hog barbecue

• Close out your evening with a glass of wine at Bin 152—casual, candlelit, and mellow (and don’t be afraid to ask for a wine rec—they love to chat.)

💡 High Low Tip: I’m happy to secure hard-to-get reservations or suggest a spot that fits your vibe—whether that’s upscale and buzzy or casual with a cult following.

👋 Day 4: Farewell

Want to stay longer? Let’s talk about adding Savannah, Georgia to your itinerary.