Discover Charleston

An Ideal Weekend in Charleston, According to a Chief Concierge

Chief concierge at The Dewberry Hotel offers insider tips about what makes Charleston timeless and attractive.

Larry Crosby attended the College of Charleston and never left the city. He has been the chief concierge at The Dewberry Hotel since before the hotel opened in July 2016. He proudly boasts that he’s a member of the “hard-hat crew.” Larry is a member of the prestigious Les Clefs d’Or association of concierges.

The hotel, originally a federal office space built in 1965, has been restored with upscale Mid-Century modern design features. Think Mad Men with Southern charm.

Larry Crosby
Larry Crosby (©The Dewberry Hotel)

What do you love about living in Charleston?

My biggest love for Charleston is its rich history. With over 350 years of pages to turn, Charleston has so many layers that are waiting to be discovered. The weather and food scene also help makes it incredible.

What question do you get asked most frequently?

The most-often-asked questions are related to dining. Guests always want to get the scoop on the most trendy, hip, and local spots to eat their way through the city. Our food scene is constantly evolving and we’ve become one of the culinary centers of the South.

McLeod Plantation in Charleston
(©McLeod Plantation Historic Site)

What do you recommend to first-time visitors?

The Charleston City Market, the Old Slave Mart museum, McLeod Plantation, the Battery and Angel Oak.

What’s your ideal Charleston weekend itinerary? 

An ideal Charleston itinerary starts with a local guide to introduce you to the city on foot. The architecture and beauty is best seen strolling the streets with a historian who will help tell the evolution of the city. After the tour, go to some of the museum homes, such as the Nathaniel Russell House, a history museum, such as the Old Slave Mart and peruse the city market. That will cover most of the first day. At night, eat and drink at one of our many amazing restaurants!

On the next day, I would start at the Saturday Charleston Farmers Market at Marion Square. I would take a casual stroll to eat and have coffee at one of the many food vendors. There’s live entertainment, arts and crafts, and it’s a great place to people-watch. After the market, I would consider going to one of the area beaches such as Sullivan’s Island. You could relax, enjoy lunch and return for a mid-day massage at our Dewberry Spa. After the appointment, drink at the Living Room followed by an evening sunset sailing charter. That would be a good way to end a very relaxing day.

On Sunday morning, I would head out to McLeod Plantation to take their fantastic interpretive tour. It’s a cultural experience that shouldn’t be missed. After the tour, have Sunday brunch at one of the city’s many wonderful brunch spots then go shopping on King Street. You want to make sure you check out the many boutiques King Street has to offer.

What is your favorite fun fact about the city? 

Charleston is a city of many firsts – the first golf course (Harleston Green), playhouse (Dock Street Theatre) and more. We are also home to Gadsen’s Wharf, the site of the upcoming International African American Museum. This site is the wharf where an estimated 40 to 50 percent of West African slaves were brought into America to be auctioned and sold.

Dock Street Theatre
(Courtesy Dock Street Theatre)

What is the most extravagant request you’ve received?
No request is too extravagant! I’ve had my share of interesting itineraries but that’s what I enjoy the most. I welcome the challenge of creating unique, authentic and memorable experiences for all of our guests.

Is there a little known experience that you recommend?
Sunset Cay Marina has some of the most beautiful sunsets in the area. Also, you can take a private boat from the marina to the backside of Kiawah Island which gives amazing views of the undeveloped side of the island.

What are people most surprised by when they visit Charleston?
I believe people are most surprised at how friendly, hospitable, historic, beautiful, and amazing the food our city has and represents. You can read about it in travel magazines and blogs but when guests arrive, it’s incredible to see how much we live up to the reputation of being the No. 1 city in the US.

What’s your favorite Charleston souvenir?
My favorite souvenir is an authentic Sweetgrass basket. There are many locations to purchase but the most convenient is the Charleston City Market. There are also stalls along Highway 17 North. I also love a traditional Charleston rice spoon for a souvenir. They have some really well-crafted ones at the Historic Charleston Foundation.

People sitting at 167 Raw Bar
(Courtesy 167 Raw Bar)

What are your favorite restaurants?

Favorite cocktail bar? Favorite rooftop bar?
My favorite cocktail bar is The Living Room. The drinks are outstanding and atmosphere is chic. Belmont and Gin Joint craft some really good libations as well. Another local’s favorite is The Faculty Lounge. It’s a place where they have some of the best bartenders in town. I can tell them what spirit, and they have crafted some of the most interesting drinks I’ve had.

What do you do when you’re not working?
When I’m away from The Dewberry, I’m usually on the golf course, happy hour, or the beach. I love the outdoors so whether it’s spending time a boat, playing a game of basketball, or sinking a crucial birdie putt, you can find me enjoying our lovely weather. I’m also an avid homebrewer so I always have time for a pint!