The Holy City: Where Cobblestones Meet the Sea

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Advisor - Jodi Grooms
Curated By

Jodi Grooms

  • City Travel

  • Arts & Culture

  • Nature Escapes

  • Charleston

  • History

  • Architecture

Advisor - The Holy City: Where Cobblestones Meet the Sea
Curator’s statement

I fell in love with wandering Charleston’s historic streets, where every corner revealed stunning architecture and beautiful churches that took my breath away. The harbor cruise was a highlight of my trip, taking me out to Fort Sumter—where the Civil War began—while also giving me incredible views of the elegant Southern-style homes lining the waterfront. Magnolia Gardens was absolutely magical—the landscapes were so breathtaking that I found myself completely immersed in the natural beauty and tranquility. Charleston captured my heart with its perfect blend of rich history, architectural charm, and stunning scenery that made every moment feel special.​​​​​​​​​​​​​​​​

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Where to stay in Charleston

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Things to do in Charleston

Lost in the enchanting landscapes of Magnolia Gardens, where every view feels like a painting

Harbor cruise to Fort Sumter

The harbor cruise was one of the most memorable parts of my Charleston adventure. As we glided through the historic waters, I was transported back in time to Fort Sumter, the pivotal Civil War site sitting majestically in the middle of Charleston Harbor. The ferry ride offered breathtaking perspectives of the city’s coastline, where elegant Southern-style homes lined the waterfront like pearls on a string. Seeing these grand mansions from the water gave me a unique appreciation for Charleston’s architectural heritage and its deep connection to the sea.

Magnolia Plantation & Gardens

At Magnolia Gardens, nature and design came together in perfect harmony. In the gardens, magnificent magnolia trees create a canopy of beauty overhead. The carefully curated landscapes unfolded like scenes from a painting, each turn revealing new vistas of blooming flowers, peaceful water features, and moss-draped trees. The serenity of the gardens provided a perfect counterpoint to the bustling historic district, offering a peaceful retreat where I could truly absorb the natural splendor of the Lowcountry. Still, the four restored enslaved cabins on the property were an important reminder of the gardens’ difficult history.

Walking Charleston’s historic streets

Wandering through Charleston’s historic district was like taking a stroll through living history. The cobblestone streets beneath my feet told stories of centuries past, while every corner revealed architectural treasures that left me in awe. The city’s famous churches rose like elegant sentinels throughout the streetscape, their distinctive spires creating the skyline that has earned Charleston the nickname “The Holy City.” From Rainbow Row’s pastel facades to the intricate ironwork balconies, each building was a testament to the city’s rich architectural heritage and Southern elegance.

Mount Pleasant sunset

My visit to Mount Pleasant provided the perfect finale to my Charleston experience. Watching the sun set over the water was absolutely breathtaking—one of those moments that stays etched in your memory forever. As the golden light danced across the harbor waters, painting the sky in brilliant oranges and pinks, I felt completely captivated by the natural beauty of the South Carolina coast. The peaceful waterfront setting in Mount Pleasant offered the ideal vantage point to reflect on all the wonderful experiences of my Charleston journey while witnessing one of nature’s most spectacular daily performances.

Angel Oak Tree on Johns Island

Visit this magnificent 400-year-old Southern live oak that stands 65 feet tall with branches stretching over 180 feet wide. Walking beneath its massive, moss-draped canopy feels mystical—the ancient twisted limbs create a natural cathedral that’s both humbling and awe-inspiring. It’s a perfect complement to your other Charleston experiences, showcasing the timeless natural beauty of the Lowcountry.​​​​​​​​​​​​​​​​

Places to eat & drink in Charleston

Fleet Landing: A Charleston institution where naval history meets exceptional seafood

Fleet Landing

Perched right on the waterfront, this converted naval building offers fresh seafood with stunning harbor views, making it the perfect spot to watch boats pass by while enjoying Lowcountry classics.

FIG

A local neighborhood restaurant with professional service, a convivial, comfortable atmosphere, and regional menu with honest and simple preparations. Run by two James Beard award-winning chefs, it’s been a Charleston staple since 2003, with approachable fine dining.

Husk

Located in historic downtown Charleston, Husk remains at the forefront of thoughtful Southern cuisine, focusing on a modern approach to Southern ingredients in a beautifully restored Victorian mansion.

The Ordinary

A Southern seafood hall and oyster bar located in an old bank that celebrates the “merroir” of the Coastal Carolinas with an impressive raw bar and creative seafood dishes in a stunning historic setting.

Peninsula Grill

A romantic fine-dining restaurant known for its award-winning coconut cake and elegant Southern cuisine, housed in a historic inn with intimate courtyard dining and impeccable service.

Need to know

Getting around

  • Parking can be challenging in the historic district. Arrive early at popular waterfront restaurants like Fleet Landing or consider walking or rideshares for downtown dining.

  • The best way to see the historic architecture and churches is on foot. Wear comfortable walking shoes for those cobblestone streets.

  • Plan extra time for harbor tours—they’re incredibly popular and the views of Fort Sumter and waterfront homes are worth it.

Must-do experiences

Don’t miss the sunset views from Mount Pleasant—it’s absolutely breathtaking and a perfect way to end your day.

Magnolia Gardens is a peaceful escape from the busy historic district. Allow at least two to three hours to fully enjoy the landscapes.

Consider visiting Angel Oak Tree if you have time—it’s a short drive but an unforgettable natural wonder.

Dining strategy

  • Make reservations well in advance for popular local restaurants like FIG and Husk.

  • Fleet Landing gets busy quickly due to its prime waterfront location—go early or be prepared to wait.

  • Try to experience both casual waterfront dining and upscale Lowcountry cuisine to get the full Charleston food scene.

Photography tips

  • The gardens and moss-draped trees are incredibly photogenic. Bring your camera everywhere.

  • Early morning and late afternoon provide the best light for capturing the architecture and Spanish moss.

  • The harbor views from both the water and Mount Pleasant offer completely different but equally stunning perspectives.

Timing

  • Spring and fall offer the most comfortable weather for walking tours and outdoor dining.

  • Allow more time than you think for each activity. Charleston’s charm makes you want to linger everywhere​​​​​​​​​​​​​​​​.

Advisor - Jodi Grooms

Travel Advisor

Jodi Grooms

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