Highlights of Downtown Charleston: A Local’s Guide

Welcome to TMB Living: Coffee & Conversations, where real estate, design, and everyday life come together, helping you love where you live. Today’s coffee stop is Second State Coffee, one of my favorite cafés in Charleston, and the perfect starting point for a walking tour through our beautiful historic downtown.

As locals, it’s easy to take Charleston’s treasures for granted. But every so often, it’s worth playing tourist in your own town. Here are some of my favorite highlights of downtown Charleston, places that always remind me why I love calling the Lowcountry home.

Rainbow Row

Charleston’s most photographed landmark never loses its charm. The pastel-colored homes lining East Bay Street are iconic, with history behind every facade.

Just across the street, there’s a dog park tucked next to a cobblestone street, a spot I’ve visited often. My mother’s cousin once lived nearby and was known for welcoming strangers into her garden and courtyard, always ready to share Charleston’s hospitality.

Horse-Drawn Carriage Rides

Love them or find them a bit inconvenient in traffic, horse-drawn carriages are a Charleston staple. They offer visitors a unique way to hear the city’s stories while clip-clopping through downtown’s historic streets.

Waterfront Park & the Pineapple Fountain

A must-visit for families, couples, or anyone who wants to enjoy the harbor breeze. Kids splash in the fountains, sailboats drift by, and everyone takes the classic photo at the Pineapple Fountain, including some of my past clients, who insisted on capturing their “Charleston moment” there.

The City Market

Since the 1800s, the Charleston City Market has been a hub of commerce and culture. It’s still a joy to wander through, with local artisans displaying their work. I always make a point to stop by and support friends who exhibit there.

King Street

King Street is Charleston’s premier shopping corridor, filled with boutiques, antiques, and local shops. On Second Sunday, the street closes to traffic and transforms into a community festival with outdoor dining and mingling, one of the best times to experience its energy.

The Battery & White Point Garden

At the tip of the peninsula lies the Battery and White Point Garden, where historic mansions overlook Charleston Harbor. It’s a favorite spot for photos, leisurely walks, and enjoying the shade of centuries-old live oaks. Cannons and monuments remind visitors of the city’s layered past, while the waterfront views speak for themselves.

Dock Street Theatre

Did you know Charleston is home to the first theater in America? The Dock Street Theatre now hosts Charleston Stage productions. Friends of mine volunteer as ushers there, a wonderful way to enjoy live performances while giving back to the community.

Gibbes Museum of Art

The Gibbes Museum celebrates Charleston’s artistic heritage with an impressive collection of local and historic works. A personal favorite is the Miniatures Collection, which inspired my family friend Katherine Scott Crawford’s book The Miniaturist Assistant. It’s a reminder of how Charleston’s history continues to influence art and storytelling today.

Aiken-Rhett House

Unlike many restored properties, the Aiken-Rhett House has been preserved, offering a raw and powerful glimpse into 19th-century Charleston life. Touring this home with the Charleston Magazine Club gave me a deeper appreciation for the city’s history, both the grandeur and the grit.

Closing Thoughts

These highlights are just a small slice of what makes downtown Charleston so special. Whether you’re a longtime resident or a first-time visitor, it’s always worth setting aside an afternoon to rediscover our city’s charm.

I’m Trudy Mercy Brown with TMB Living Real Estate & Interiors. Whether you’re visiting, relocating, or already calling Charleston home, I’d love to help you love where you live.