Charleston, South Carolina is a city with rich history, architecture, culture, art, & natural beauty.

This city truly has something for everyone, making it a top choice for the host city of our upcoming live event for the Top 5% of Real Estate Professionals,  ‘Raising The Bar’. 

We’re happy you’ll be joining us in this beautiful and historic city this October!

Art lovers, get ready. Foodies, get ready.  Live Music and Theater lovers, get ready. Nature Lovers, get ready. MEC friends, get ready!!

Charleston is South Carolina’s largest, most historic, and beloved city. It was the fourth largest city in Colonial America and is often ranked one of the best cities in the U.S.. In 2016 Travel + Leisure Magazine ranked Charleston as the best city in the world.

A port city with a beautiful harbor, Charleston is known for its cobblestone streets, horse-drawn carriages, and antebellum architecture. 

When joining us in Charleston for Raising The Bar, you’ll find yourself with evenings free to explore this iconic city. 

We’ve compiled the following list of MEC’s favorite things to see, do, eat, and drink during the evenings in Charleston, South Carolina. 

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Tours

We’ll start here because the city, especially the historic downtown and waterfront, are among the most beautiful and not-to-miss parts about being in Charleston, SC! 

Whether you plan to tour the city with your real estate team or go on a solo exploration, these are the BEST ways to see Charleston!

1.Evening Horse-Drawn Carriage Tour of Downtown Charleston, SC

A carriage ride through Charleston is perhaps the most iconic experience a first-time visitor to the city can have. The open-air carriages ride through the historic district from their starting point in City Market. Professional tour guides point out city landmarks and tell funny and fascinating stories of the people who shaped Charleston into the place it is today.

The tours are professionally guided and regulated by the city. The health of the animals is also monitored by the city. The routes for every tour company are the same since they are picked by the city to minimize the disruption to traffic. Your tour guide draws your tour route from a city kiosk just before departing. You will not know which of the four available tour sections you will embark on prior to booking your tour. Rest assured that every tour section is beautiful and fascinating in its own way.

If you book your tour through Palmetto Carriage Works, your tour may be guided by draft horses or by a team of mules. You can also meet their mules by heading over early and visiting their big red barn on Guignard Street.

A Southern-style carriage ride is a classic activity in Charleston. A quick tour offers a look at the historical sights of downtown and the Commercial District. Relax while you ride through the streets, from Joe Riley Waterfront Park past the City Market to the Old Exchange and Provost Dungeon.

More info here. 

Know before you go: 

The duration of this professionally guided tour from Palmetto Carriage is 35 minutes. That’s a good amount of time to see the sites and catch a great meal during the evenings.

Mobile tickets are accepted. Cancellations are accepted with at least 24 hours advance notice and gratuities are appreciated.

Most times of the year, an advance ticket purchase is not required. During holiday and festival weekends, advance purchase is recommended.  Raising The Bar is Columbus Day Weekend, so expect the tours to be more popular during this time. 

2. Haunted Evening Horse and Carriage Tour of Charleston

If you’re interested in a spookier version of the classic carriage tour, consider taking one of the haunted evening carriage tours!

Hear Charleston’s spooky history on this haunted horse and carriage ride. Part ghost tour and part history tour, this evening outing does double duty as it takes you to top Charleston sights such as the Mills House and Old Exchange Building, navigating cobblestone alleyways and twisting side streets with ease. Your guide entertains you with haunted Charleston history as you make your way through the heart of the Holy City.

You can find more information on this tour here. 

Whether you and your team choose to take the classic or haunted rides, here is a helpful link to the 5 Things To Know Before Your Carriage Ride.

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Tours on Foot

Whether you choose to embark on a self-guided tour or book a walking tour through a professional guide, you’ll experience Charleston’s rich history, beauty, and charm with a stroll through the downtown area.

Historic Downtown Charleston is best explored by foot, and the mystery, romance, and charm of the city make for an amazing walking tour.

There are many companies offering daily tours led by native Charlestonians who are eager to share their unique stories and insights with you!

3. Charleston Ghost Tour: Two Bars, One Graveyard, and a Ghost Story

It’s a bar crawl, history walk, and paranormal experience with a tarot reading for dessert. This tour is a 3-hour tour, which makes for a quality team experience.

Charleston is home to the supernatural, paranormal, and existential: 350 years of graveyards, ghosts, and ghouls in a drinking town with a history problem. 

Related: 5 Haunted Facts About Charleston

Starting at one of Charleston’s most notorious watering holes, an upscale dive, you’ll begin your experience at the bar. Listen to ghost stories and tales of Charleston’s darker side while enjoying your favorite beverage.

From the bar, you’ll walk to a graveyard where you’ll learn how to see a ghost, and along the way, you may even answer the questions, “Are we alone?,” and “Why are we here?”

From the graveyard, you’ll walk to another bar where you’ll finish the evening with more history and ghost stories and a tarot reading.

Find more info on this tour here

If scary ghost stories aren’t your thing, we recommend taking a ‘hoppier’ tour!

4. Charleston History and Hops Tour – Bar and History Walk

This 2-hour tour experience is for guests who enjoy sipping their way through a new city full of history. This is not a classic “sit there and shut up tour” but an opportunity to engage with a local. The licensed guide will meet guests at the initial bar establishment and receive a small complimentary snack and the opportunity to purchase some of the area’s finest beers/ mixed drinks while the guide goes over the historical roots of the city.

From there, guests will walk the historical alleyways and cobblestone streets of Charleston to several cultural sites including a dungeon, the original city theater, and 300-year-old homes.

A second bar will be the site of another drink opportunity where the guide will relate stories specifically regarding the Prohibition era in Charleston and its effect on the populace. Towards the end of the experience, guests will find themselves in a beautiful local park along the waterfront.

View Tour Details here.

Related: 15 Best breweries in Charleston

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Harbor Tours

There are many opportunities for evening tours of the exquisite Charleston Harbor. Take a sunset sail or an evening dinner cruise with your team. 

5. Sailboat Cruises Aboard Schooner Pride

Get an up-close-and-personal look at Charleston Harbor on Charleston’s only 3-mast tall ship. People of all walks of life can enjoy two-hour public sails! There are no set courses; she sails with the winds and tides, so every cruise is unique. You will always be in the sheltered harbor area and see all the sites—just closer to some than others.

Watch a gorgeous Charleston sunset while enjoying this two-hour sail aboard the Schooner Pride. Sit back and relax on deck while the sun drops slowly towards the horizon, illuminating the countless steeples of the Holy City.

Discover the tranquility of cruising the historic Charleston Harbor on a genuine tall ship, powered only by the wind in our sails.

The Schooner Pride, is an 84-foot, three-mast schooner modeled after the classic coastal trading schooners. She is an authentic tall ship and possesses all the character and class of a ship designed during the great days of sail. She is USCG certified to hold up to 49 passengers.

View tour information here. 

6. Charleston Harbor Tours

Climb aboard the Carolina Belle to enjoy the beauty of the Charleston Harbor and learn the rich history of the Holy City. During the scenic and relaxing 90-minute tour, you will see over 75 landmarks and points of interest, including stunning close views of Fort Sumter!

Your professional USCG licensed captain will narrate history, sights, and facts about the Charleston Harbor as you pass locations critical to the history of the United States.

View Tour Info Here.

7. Sunset Dinner Cruise and Harbor Tour

The Charleston Harbor is a magnificent backdrop for dinner. Throw in a sunset and a cruise, and you have yourself a great way to spend the evening.

SpiritLine Cruises offers a true waterfront dining experience in Charleston. 

Aboard the Spirit of Carolina, you and your guests will enjoy a three or four-course dinner, made to order from local seasonal ingredients.  

As you dine on a delicious multi-course plated dinner, the Spirit of Carolina will cruise through the beautiful Charleston Harbor, past Fort Sumter, along the Battery, and beneath the Ravenel Bridge.  It’s an unforgettable evening on the water.

View tour info here. For groups of 15 or more, check out their Group rates.

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Live Music, Comedy, & Theater

Charleston displays a rich connection to art and culture. Whether you have a love of art and theater, or you’re just looking for something fun to do during your time in Charleston, the live music culture and the theater opportunities are an impressive part of Charleston’s appeal. 

8. Holy City Magic

Holy City Magic is an intimate magic theater and bar located in the heart of beautiful Charleston, SC.  Holy City Magic is more than just a show venue. It provides a  unique night-out experience. 

Located at 49 ½ John Street (corner of King & John) in the heart of downtown, this beautiful theater and speakeasy-style bar is a historic 200-year-old building, and you can still see the darkened floors from a Civil War building fire.

Upon entering, you will enjoy closeup magic at the bar situated in a magic-themed lounge area.  At showtime, you will take your seats in front of a stylish stage to enjoy a rotating schedule of shows featuring world-renowned magical and variety entertainment.

Their evening shows are touted as “not the magic show you remember as a child.”

Holy City Magic offers fun evening shows geared toward an adult audience.  The evening starts with a cocktail hour featuring close-up magic out our bar, followed by a fun, hour and a half show with an intermission. Shows feature their resident magician or one of their nationally renowned guest performers!

View their show info here. 

9. Black Fedora Theater

Located at 164 Church Streets, steps from downtown’s City Market, this fun, lively, and cozy theater sells its shows out quickly. 

They offer audience-interactive comic mysteries that run most evenings. You’ll enjoy one of their many comic whodunits Inspector NoClue’s Murder Mystery, Church Street Daughters of the Late Unpleasantness Garden, Gun, and Gin Club, Sherlock’s Other Brother by a Southern Mother, and their latest, Murder Aboard the Starship Fed Ora!

Volunteer to play a character or choose to stay out of the spotlight and enjoy some tasty appetizers or something from the beer/wine/dessert bar!

View their show schedule and info here. 

10. Prohibition Charleston

A nod to the classic 1920’s speakeasy, Prohibition feels like you’re stepping back in time with its vintage-inspired decor, offering cocktails and cuisine that are anything but old-fashioned. 

We love Prohibition for the inventive hand-crafted cocktails and the sophisticated food menu offerings. They offer a casual tasting menu and live music every Thursday from 10 pm until 1 am, which happens to be one of the nights we’re in town for ‘Raising The Bar’. 

View more info about Prohibition’s offerings here.

For a complete guide to live music, comedy, and theater in Charleston, SC – check out this link.

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Shopping

Charleston does not disappoint when it comes to shopping! There are many great spots in the immediate downtown area that give you a one-stop shopping opportunity. Whether you are interested in shopping from local merchants, cute boutiques, or high-end retailers – Charleston has something for you! Bring some spending money!

11. Historic King Street Shopping

King Street is a bustling thoroughfare where Charleston’s past and present meet. At more than 300 years old, King Street is the second most historically and architecturally significant street in downtown Charleston after Meeting Street. It was named for King Charles II of England and was the main route in the old city of Charles Towne. Hosting a variety of high-end specialty shops, it surpassed every other location, including East Bay Street and the pier.

King Street boasts some of the city’s trendiest restaurants and sophisticated cocktail scenes along with hotels, art galleries, flourishing businesses, and lively nightlife – not to mention some seriously exceptional shopping. U.S. News and World Report named King Street one of the country’s “Top 10 Shopping Streets.”

When walking through the middle of the Charleston peninsula, its wide, pedestrian-friendly sidewalks, chic boutiques, antique shops, three-story brick and buildings, and central location make it easy to see why King Street is an unforgettable dining and shopping King Street hosts many events, including Marion Square’s weekly Saturday Farmer’s Market, Second Sundays on King Street, Charleston Fashion Week, Food + Wine Festival, Piccolo Spoleto Festival, Southeastern Wildlife Festival, and various parades. Plus, the world-famous Cooper River Bridge run also makes its way down King Street. And think – to explore this incredible cultural and retail hub, all you have to do is visit.

For more tips, check out the ultimate guide to shopping on King Street in Charleston, SC.

12. Historic Charleston City Market

Located at 188 Meeting Street, the market is an AMAZING central location that features dozens of local artists, shops, and vendors who sell their products here each day.

It is a neat experience to walk through the market and see all of the products.

The City Market is a historic market established in the 1790s. The market stretches for four city blocks from the architecturally-significant Market Hall, which faces Meeting Street, through a continuous series of one-story market sheds. 

Following Hurricane Hugo in 1989, the building was restored by the City of Charleston and received a Carolopolis Award from the Preservation Society in January 2003.

The building was repainted in its original colors, which included strong ochre coloring and bright green ironwork.

Learn more about City Market here. 

Here is a helpful link for parking downtown.  Where to Park in Downtown Charleston – City Parking Garages

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The Dining Experiences

Many people come to Charleston with one thing on their minds: food. Just ask MEC Founder + Head Coach, Bill Middleton. He has, on more than one occasion, made the two-hour drive from his home on Hilton Head Island, for a meal you can only get in Charleston!

From the best Shrimp and Grits you’ll ever have to the desserts you’ll want to have right now, we’ve got your must-stops on the list below!

13. S.N.O.B – Slightly North Of Broad

When compiling our list of favorite restaurants, this one was on the top of all of our minds!  This is a MEC favorite, and is located at 192 East Bay St, just a short walk from City Market, close to shopping, art galleries, and more!

S.N.O.B is an eclectic Lowcountry bistro that brings together an abundance of fresh, local ingredients and thoughtful, expert presentation with friendly, contagious energy.

They source their vegetables, meats, eggs, and dairy from local farms. Their beverages, beers & spirits are also locally sourced.

We HIGHLY recommend the Shrimp and Grits –  House Sausage, Country Ham (yes….it’s a thing), tomatoes, green onions, garlic, Marsh Hen yellow grits, and the most deliciously prepared shrimp that you’ll dream about for a good while. 

S.N.O.B. is open for dinner nightly beginning at 5:00 p.m. 

Lunch is served Monday through Friday from 11:30-2:30. 

Live music nightly! 

View their menu here. 

14. Lewis Barbecue

Remember that meal that Bill often drives to Charleston for? Yeah, it’s this one!

464 North Nassau St is a little off the beaten path of the downtown corridor, but certainly worth the minimal amount of travel time. 

The first thing you’ll notice when you pull up to Lewis Barbecue is the massive, custom-made smokers, welded by the pitmaster himself. Inside you’ll order at the counter, where John Lewis is slicing up true Central Texas barbecue, cut-to-order. They also have a huge bar and backyard patio to keep you entertained year-round.

The menu is simple and offers large slabs of melt-in-your-mouth brisket, smoked sausages, and an array of sides, like corn pudding and tangy coleslaw. Your meat is sliced and portioned on the plate. It feels a lot like a picnic with friends!

This is a place to indulge in savory deliciousness, and may not be enjoyed by vegetarians. One Charleston reviewer of Lewis Barbecue simply said “meat sweats”, and they meant that in the best way possible.

View their menu here.

No Reservations Required.

15. Taco Boy

We LOVE Taco Boy for so many reasons. It’s our go-to for Mexican and Margaritas while in Charleston!

There are two Taco Boy locations in the Charleston area. The closest to downtown is the location at 217 Huger St. 

In addition to their yummy food and eclectic atmosphere, Taco Boy gives back to the local Charleston community!

Taco Boy champions issues that help children in the community. They also teamed up with local restaurants in 2020 to begin two initiatives  ‘Pay it Forward’ & ‘Southern Restaurants for Racial Justice’. 

We love that they believe in and promote initiatives that inspire their staff to grow from within!

The Taco Boy atmosphere is relaxed and casual. The decor is a colorful eclectic vibe and adds fun to the overall experience.

Our menu favorites are the Mexican Street Corn, Kimchi Beef tacos, and the Ceviche.

Our favorite drink options are the Blood Orange Margarita, the Michelada, or the Tepachito.

View their menu here. 

We’ve saved our dessert for last!

16. Carmella’s Cafe and Dessert Bar

They tout themselves as a tranquil eatery featuring sandwiches & charcuterie, classic Italian desserts, wine & cocktails. To us, they are so much more!

Located at 198 East Bay Street in historic downtown Charleston, SC, Carmella’s Cafe and Dessert Bar is an Italian-American dessert boutique cafe specializing in gourmet cakes and pastries, gelato and sorbet, and ciabatta sandwiches, as well as specialty adult cocktails and milkshakes, fine wine and local beer.

 Our favorites are the Chocolate Bread Pudding, Carrot Cake, and Tiramisu.

Carmella’s is open from 11 am to midnight daily. View their menu here.

Explore more of Charleston’s best dining experience by viewing the Conde Nast Traveler list of The 31 Best Restaurants in Charleston. 

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We look forward to exploring Charleston, SC with you this October 6th & 7th for Raising The Bar!

View event details and purchase tickets at www.MECRaisingTheBar.com