Charleston, South Carolina, isn’t just a charming coastal city—it’s a place rich in history and tradition. Known as The Holy City for its religious tolerance and skyline dotted with historic church steeples, Charleston has long been a sanctuary for diverse faiths. This deep-rooted history blends seamlessly with cobblestone streets, pastel-hued houses, centuries-old oak trees draped in Spanish moss, and the unmistakable scent of Southern comfort food in the air. Whether you’re a history buff, a foodie, or just looking for coastal charm, Charleston feels like stepping into a storybook.

This four-day itinerary blends history, cuisine, outdoor adventure, and relaxation—so you can experience the best of the Holy City, no matter your travel style.

Day 1: Historic Charm, Architecture & Southern Hospitality

Charleston’s rich history is one of its biggest draws, and today is all about immersing yourself in the city's stunning architecture, historic homes, and classic Lowcountry flavors.

Start your Charleston adventure with a visit to Miller’s All Day, a beloved breakfast spot serving up shrimp and grits, homemade biscuits, and a fun retro diner vibe. It’s the perfect way to fuel up for a day of exploring. After breakfast, take a leisurely stroll through Charleston’s Historic District. Wander past the famous pastel-colored homes of Rainbow Row, admire the stately mansions along The Battery, and soak in the city’s undeniable charm. For a deeper dive into Charleston’s past, step inside one of its iconic historic homes. You can choose between Nathaniel Russell House (a Federal-style mansion with intricate details and a compelling history) or Aiken-Rhett House (a preserved 19th-century home that offers a deep dive into Charleston’s complex past).

By lunchtime, head to 167 Raw, a small but mighty seafood bar serving up fresh oysters, lobster rolls, and their famous tuna burgers. Spend the afternoon wandering through the Charleston City Market, one of the nation’s oldest public markets. It’s a great place to pick up unique souvenirs, including the city’s famous sweetgrass baskets. For a relaxing change of pace, hop on a horse-drawn carriage tour and let a local guide narrate Charleston’s fascinating history as you clip-clop through its charming streets.

As the evening rolls in, treat yourself to a memorable dinner at Husk, where chef-driven Southern cuisine shines in a beautifully restored historic home. Wrap up your first day with a cocktail at The Vendue Rooftop, where you can soak in breathtaking panoramic views of the Charleston skyline as the sun dips below the horizon.

Your Sunday Morning Escape

Day 2: Plantations, Beach Time & Sunset Views

Today is all about stepping beyond downtown Charleston to experience the area’s natural beauty, rich history, and unbeatable coastal vibes. Day two takes you beyond downtown Charleston for a mix of history, nature, and waterfront dining.

Start your morning with a stop at Callie’s Hot Little Biscuit, where you can indulge in buttery, flaky goodness that has become a Charleston staple. Whether you go for a classic buttermilk biscuit or something a little more adventurous, you can’t go wrong. After breakfast, take a short drive to one of Charleston’s stunning historic plantations. Whether you choose Middleton Place, known for America’s oldest landscaped gardens, or Magnolia Plantation & Gardens, where wild beauty meets rich history, you’ll be transported back in time (watch for alligators!).

For lunch, head to Bowens Island Restaurant, a no-frills seafood shack known for its fresh oysters and unbeatable waterfront views. Grab a picnic table, order a platter of seafood, and soak in the coastal atmosphere. Spend your afternoon unwinding at Sullivan’s Island. Whether you prefer lounging on the sandy shores, taking a refreshing dip in the Atlantic, or exploring Fort Moultrie, a Revolutionary War site, this beach town offers the perfect mix of relaxation and history.

As the day winds down, treat yourself to dinner at The Ordinary, a lively seafood hall where towering shellfish platters and Lowcountry flavors take center stage. Cap off the night with a sunset cruise in Charleston Harbor. Sip on a cocktail as you watch the sky turn shades of pink over Fort Sumter and the Ravenel Bridge—the perfect way to end another unforgettable day.

Get Inspired Every Week

Day 3: Outdoor Adventure & Culinary Delights

Mixing history, adventure, and some of Charleston’s best eats, today is packed with excitement and unforgettable experiences. Mixing history, adventure, and some of Charleston’s best eats, today is packed with excitement.

Start your day with a leisurely brunch at Poogan’s Porch, a charming historic home-turned-restaurant. Whether you go for their famous biscuits or the indulgent fried chicken & waffles, this spot is a Charleston classic. After brunch, head to Shem Creek for a bit of adventure. Rent a kayak or paddleboard and glide through the scenic waterway, where you might spot dolphins playing in the waves alongside you.

For lunch, make your way to Leon’s Oyster Shop, where you can feast on crispy fried chicken, chargrilled oysters, and their signature frozen gin & tonic—a perfect midday pick-me-up. Spend the afternoon at Patriots Point Naval & Maritime Museum, home to the massive USS Yorktown aircraft carrier. Walk through the decks, explore historic exhibits, and get a feel for Charleston’s military past. Before dinner, stop by Boone Hall Plantation, one of the most photographed plantations in America. The breathtaking oak-lined driveway is straight out of a movie—literally, as fans of The Notebook might recognize it.

For dinner, indulge at Fig, a James Beard Award-winning restaurant that takes Southern cuisine to the next level with farm-fresh ingredients and creative flavors. Wrap up your day with live jazz at The Commodore, a retro-style club where the music is lively, the drinks are strong, and the vibe is unbeatable.

Day 4: A Laid-Back Farewell to Charleston

Your final day in Charleston is all about slowing down and making the most of your final moments in this charming city.

Start your day with a leisurely brunch at The Obstinate Daughter on Sullivan’s Island. This Southern-meets-Mediterranean eatery is famous for its fresh pastries and seafood-forward dishes—perfect for a relaxed and satisfying send-off. After brunch, take a stroll down King Street, Charleston’s shopping hub. Whether you’re in the mood for antique treasures, trendy boutiques, or local art, there’s something for everyone. Before heading out, take a walk through Waterfront Park. Snap a photo at the famous Pineapple Fountain, breathe in the salty air, and take in the beautiful harbor views.

For one final taste of Charleston, grab a meal at Rodney Scott’s BBQ. With legendary pulled pork and hushpuppies, it’s the perfect way to wrap up your trip with some classic Southern comfort food. As your time in Charleston comes to an end, you’ll leave with a full heart (and likely a very full stomach), already dreaming of your next visit.

Why Charleston Will Keep You Coming Back

Four days in Charleston is just enough to fall in love with its rich history, unforgettable cuisine, and coastal charm. From grand mansions and storied plantations to fresh seafood and vibrant Lowcountry flavors, every moment here feels special. Whether you're exploring historic streets, kayaking through scenic marshes, or simply soaking in the Southern hospitality, Charleston has a way of calling you back for more.

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