For a good overview of Charleston’s historic district and a taste of its culinary scene, three to four days is ideal. A shorter trip will allow you to see the highlights, while a longer stay (over five days) lets you explore further afield, including nearby plantations and beaches while delving deeper into the city’s history and culture.

Charleston hosts a full calendar of annual events, including the renowned Spoleto Festival USA, the Charleston Wine + Food Festival, the Southeastern Wildlife Expo, the Lowcountry Oyster Festival, and the MOJA Arts Festival, attracting visitors from around the world and showcasing the city’s culture and spirit.

Shopping
King Street is known as a shopper’s paradise. This bustling thoroughfare offers a diverse retail experience, from familiar high-end chains to unique locally owned boutiques. Beyond fashion, shoppers can discover Charleston-themed souvenirs, including books, home goods and handcrafted candles. Favorites include: Berlins, Hampden, freebird, George C. Birlant and Company, Candlefish, and Croghan’s Jewel Box.

Restaurants and Bars
There are dozens of restaurants and bars on King Street, each featuring a different type of Lowcountry cuisine. Some of the favorites include Félix, King Street Grille, The Belmont, The Charleston Grill, The Vendue, and The Darling Oyster Bar.

Charleston’s best photo spots include iconic Rainbow Row, The Battery (White Point Garden) with harbor views, and the Arthur Ravenel Jr. Bridge. Charming streets like Chalmers and Tradd showcase historic architecture. Waterfront Park and the City Market offer picturesque settings. For unique perspectives, take a harbor tour. Capture the city in golden hour and explore side streets for hidden gems. Remember, Old Town Trolley Tours provides a narrated tour, highlighting key locations and making it convenient to capture the perfect shot at a variety of these great photo spots.

Originally constructed as a defensive fortification, The Battery’s name reflects its military origins. While the physical fortifications are largely absent today, the site’s strategic importance in various conflicts, most notably the American Civil War, remains palpable.

The Battery’s contemporary form emerged in the early 19th century with the construction of a seawall, transforming the area into a public promenade. This development, coupled with subsequent landscaping efforts, resulted in the creation of White Point Garden at the southern terminus of The Battery.

The promenade offers unobstructed views of Charleston Harbor, including Fort Sumter, the location of the first engagement of the Civil War. Adjacent to The Battery, the streets are lined with notable examples of 19th-century architecture, reflecting the city’s historical prosperity.

The Battery serves as a compelling destination for visitors, encapsulating Charleston’s historical trajectory through its dual identity as a former military installation and a present-day public space.

Charleston’s charm extends beyond its well-known attractions. Here are a few local favorites:

For foodies: Skip the crowded spots and head to 167 Raw for an unparalleled oyster experience. Locals rave about Callie’s Hot Little Biscuit for a truly Southern breakfast, and FIG is a Charleston institution for farm-to-table dining. Craving something different? Xiao Bao Biscuit offers unique Asian fusion, while The Daily is perfect for a casual bite.

For explorers: Ditch the main streets and wander through the quieter residential areas. You’ll stumble upon hidden gardens, charming alleyways, and stunning architecture. A kayak or paddleboard trip in the harbor offers a unique perspective of the city.

For arts and culture lovers: Check out the Charleston City Market (seasonal) at night for a more intimate shopping experience. If your trip coincides with Spoleto Festival USA, don’t miss this world-class performing arts event.

For relaxation: Escape the city bustle with a picnic at Colonial Lake, a beautiful tidal pond loved by locals.

Historic charm: Charleston is a living history book. Its cobblestone streets are lined with beautifully preserved antebellum architecture, from grand mansions to colorful row houses.

Southern hospitality: Charleston embodies Southern hospitality with its warm and welcoming atmosphere. The locals are known for their friendliness.

Culinary scene: Charleston is a foodie paradise! It boasts a thriving culinary scene with award-winning restaurants and innovative chefs.

Sweetgrass baskets: These unique and beautiful baskets are a traditional craft of the Gullah Geechee people, descendants of enslaved Africans.

Waterfront beauty: Charleston is a coastal city with stunning waterfront views. The Battery, a scenic promenade along the harbor, is a popular spot for strolling and enjoying the sea breeze.

Festivals and events: Charleston hosts a variety of festivals and events throughout the year, celebrating everything from music and art to food and history.

Beaches: While the city itself is inland, it’s just a short drive to beautiful beaches like Folly Beach, Isle of Palms, and Sullivan’s Island.

Rainbow Row (East Bay Street): This is probably the most photographed street in Charleston, and for good reason! The row of colorful historic houses is absolutely charming and makes for a picture-perfect scene.

Legare Street: Known for its grand historic homes with lush gardens and wrought-iron gates, Legare Street exudes elegance and Southern charm.

Church Street: This street is steeped in history and features some of Charleston’s most iconic landmarks, including the Dock Street Theatre and St. Philip’s Church.

Tradd Street: Another street with beautiful historic homes and gardens, Tradd Street also has a unique charm with its gas lamps and cobblestone sidewalks.

King Street: While known for its shops and restaurants, King Street also has some beautiful architecture and historic buildings.

The Charleston Historic District is a significant and substantial area, encompassing a large portion of the city’s peninsula. While the exact acreage can vary slightly depending on how the boundaries are defined, it generally covers a considerable area, roughly bounded by Calhoun Street to the north, the Ashley and Cooper Rivers to the west and east, and the harbor to the south. This expansive district includes hundreds of blocks and historic buildings, showcasing a variety of architectural styles and periods. It’s a walkable area, though quite large, making it best explored over several days or by utilizing various transportation options like the Old Town Trolley Tours to cover greater distances within the district.

Aboard our custom-built, air-conditioned vehicles, you’ll journey through the city’s most iconic landmarks, from the historic Battery and Rainbow Row to the lively Charleston City Market and French Quarter.

The tour operates daily except for Thanksgiving and Christmas Day.

The City Tour is a 1-hour and 40-minute fully narrated tour of the historic area of Charleston.

The tour focuses on bringing Charleston’s rich history and charm to life through an engaging blend of storytelling and sightseeing. You’ll journey through the city’s most iconic landmarks, from the historic Battery and Rainbow Row to the lively Charleston City Market and French Quarter. Our expert guides provide an entertaining and educational experience, ensuring you don’t just visit Charleston — you relive it. With designated stops along the route, you’ll have the flexibility to hop off and explore while your vehicle waits, making for a seamless and immersive tour of Charleston.

Charleston is one of the oldest cities in the United States with a history stretching back to 1670 when English colonists established the settlement of Charles Town, named after King Charles II.

Charleston’s City Market dates back to the late 1700s. During that period, it was a central hub of commerce, witnessing the sale of everything from produce and livestock to dry goods. It also played a complex role in the city’s economy, serving as a place where enslaved people, despite their lack of freedom, were sometimes permitted to sell goods they produced. The market’s significance extended beyond commerce, as it functioned as a public gathering space, reflecting the social and economic dynamics of the era. Today, Charleston’s City Market and King Street are the two most popular shopping destinations in the city. Vendors offer a wide variety of goods, from locally crafted items and souvenirs to clothing, jewelry, artwork, food, and the iconic sweetgrass baskets. These intricately woven sweetgrass baskets, a Gullah Geechee tradition passed down through generations, are a true Lowcountry treasure and a testament to the enduring artistry of African-American craftspeople. Visitors can discover unique gifts, Charleston-themed treasures, and authentic Southern products.

Rainbow Row, a Charleston landmark, is a series of 13 brightly painted Georgian-style houses located on East Bay Street, between Elliott and Tradd Streets. This charming row, dating from the late 1700s, is notable for its cohesive architectural style despite the varied hues of its facades. The pastel palette, likely adopted in the 20th century, contributes to the street’s distinctive character and has made it a popular subject for photographers and artists. The juxtaposition of the historic architecture with the lively colors creates a unique visual experience, offering a glimpse into Charleston’s past while showcasing its enduring charm.

The Nathaniel Russell House: This Federal-style masterpiece is known for its stunning architecture and intricate details.

The Aiken-Rhett House: What is loved about this house is that it’s preserved, not restored. You get a real sense of what life was like, with original wallpaper, furniture, and even personal belongings.

The Williams Mansion: Known as “The Grandest Home in the South,” this place is HUGE. It’s filled with period antiques and art, and you can easily spend hours wandering through its many rooms.

The Heyward-Washington House: This is a great example of a simpler, yet still elegant, Charleston home. It’s also where George Washington stayed during his visit to the city in 1791.

The Joseph Manigault House: Another stunning example of Federal architecture, this house is known for its exquisite plasterwork and period furnishings.

A piece of history: The Pineapple Fountain was built in 1990, but it represents a much older tradition. Pineapples were a rare and expensive treat in colonial times, making them a symbol of wealth and hospitality.

Symbol of hospitality: Pineapples have long been a symbol of hospitality in the South, and Charleston is no exception. The Pineapple Fountain embodies this tradition, welcoming visitors to the city.

Picture-perfect spot: This iconic fountain is a popular spot for photos. Whether you’re a couple looking for a romantic backdrop or a family wanting to capture a fun memory, the Pineapple Fountain is the perfect place.

Waterfront Park gem: The fountain is located in Waterfront Park, a beautiful green space with stunning views of Charleston Harbor.

Typically, the first City Day Tour departs at 9:00 am from our Charleston Visitor Center, 375 Meeting Street.

Typically, the last City Day Tour departs the Charleston Visitor Center, 375 Meeting Street at 4:30 pm.

The Charleston City Tour departs every 30 minutes from 9 am until 4:30 pm.

We do not offer senior, student or military discounts. However, booking online and in advance will save you the most money and give you the best pricing.

We do not offer gift certificates, but the ticket can be booked for a certain date and then rescheduled as needed up to 24 hours in advance of the tour date.

Yes! You will board all-new luxury 2025-model vehicles with air conditioning and upgraded seats for a premium experience.

Yes, we can accommodate strollers, but they must be collapsible and will be stored up front with the tour guide. Strollers in the aisles would constitute a safety hazard.

Yes, food and nonalcoholic drinks are welcome on the tour. However, for the safety and comfort of all guests, alcoholic beverages are strictly prohibited.

Service animals are the only animals that are allowed onboard the vehicle.

Your ticket includes the 1-hour and 40-minute City Tour of Charleston. Museum and attraction tickets are extra and can be purchased at the gate.

To report a lost item or return an item you’ve found, please contact us at 854-264-8687.

25 guests.

Yes! Make your event memorable by chartering one of our all-new luxury 2025-model vehicles with air conditioning and upgraded seats for a premium experience. Please contact our office at 854-264-8687 to schedule.

One vehicle in our fleet is equipped with a motorized lift that can accommodate one scooter or wheelchair. For safe and efficient use, the lift requires a level surface with sufficient space, and the best boarding location is at the tour departure location — Charleston Visitor Center, 375 Meeting Street. We request that you give us a minimum of 24-hour notice so that we can have the proper vehicle available to accommodate. Please contact our office at 854-264-8687 to schedule in advance. Wheelchair-accessible vehicles are scheduled on a first-come, first-served basis. Collapsible wheelchairs are always welcome on any of our vehicles, and our CASTmembers are happy to assist with loading.