Weekend Getaway in Charleston

From Genteel Past to Culinary & Artistic Renaissance

Undiminished by wars or hurricanes, Charleston continues to radiate gentility. And although the city has a dark side to its history — most of its grand mansions were built, one way or another, by enslaved African-Americans — Charleston doesn’t shy away from this aspect of its heritage. 

Charleston has long drawn Civil War buffs, but more recently it has blossomed into a major culinary destination as well. Like New Orleans, Charleston is surrounded by brackish wetlands that yield a bounty of fresh seafood, and also like New Orleans, Charleston served as a major port where people from Europe and Africa influenced one another’s cuisines. The Lowcountry recipes that followed made use of readily available ingredients such as shrimp, oysters and rice, combining them in ostensibly simple but immensely satisfying dishes.

On this customizable long-weekend itinerary, visit antebellum mansions and flourishing gardens, sail to private islands to taste the local sea’s delicacies and even get introduced to the city’s new culinary visionaries. For those with special interests in military history, contemporary art, African-American history, architecture, botany, archeology, ecology or golf, there are endless unique experiences to enjoy.

Itinerary Highlights

Our itineraries are for your inspiration. Please contact a travel advisor to customize this itinerary to fit your needs.

  • A historical tour with a private guide
  • VIP culinary experience
  • Barrier islands sailing & dining excursion
  • Tour Fort Sumter with a former Marine
  • Overnight excursion to Kiawah Island

Trip Overview

Day 1 : Historic Charleston
Take a historical tour with a Charleston native.
Day 2 : Barrier Island Sailing Excursion & VIP Culinary Experience
Sail to the barrier islands that surround the city.
Day 3 : Military History Tour or Charleston by Bike
Visit key sites like Fort Sumter and the Citadel with a former Marine.
Day 4 - 5 : Kiawah Island Overnight
Enjoy an overnight stay at The Sanctuary at Kiawah Island Golf Resort.

Day 1 : Historic Charleston

Upon arriving in Charleston, you will be met by a fifth-generation native and expert guide who will help you access the top museums and historic mansions ahead of the tourist lines, get you entrée into a private mansion and gardens to experience a truly Southern tea service, and meet local characters who are the heart and soul of the city.

After your tour, you will take a private carriage ride on residential streets back to your hotel, Belmond Charleston Place, for lunch at The Palmetto Café.

Early this evening, enjoy a VIP tour of The Old City Jail, where some of Charleston’s most infamous criminals, 19th-century pirates and Civil War prisoners were punished. You will see the original structures, including cells and warden’s quarters. 

After your tour, have dinner at The Ordinary, an "oyster hall" set in a spacious former bank building. Favorite dishes include the pickled shrimp, and briny baked Otter Island oysters, served on the half-shell in rich bottarga butter (infused with roe). Try the Royal Bermuda Yacht Club cocktail, which adroitly balances sweet, citrusy and bitter flavors. 

Historic Charleston
Historic Charleston

Day 2 : Barrier Island Sailing Excursion & VIP Culinary Experience

After an early breakfast at your hotel, board a private sailing vessel in Charleston Harbor with your own crew to take a trip out to the barrier islands that surround the city. 

Visit a secluded beach for a private Lowcountry boil (a unique stew of seafood, vegetables and spices) prepared by your crew. Enjoy this local dish with wine or Champagne. You will then be escorted back to your hotel to clean up before dinner.

This evening, feel like a VIP at one of Charleston’s top tables, FIG, with a chef’s tasting menu and an opportunity to meet the people behind the food. One of Charleston’s more difficult reservations, FIG (Food Is Good) serves delicious continental- and Lowcountry-inspired dishes with local seasonal ingredients.

Sailing the barrier islands
Blue crabs of Charleston's barrier islands

Day 3 : Military History Tour or Charleston by Bike

On your last full day in Charleston, visit key sites like Fort Sumter and The Citadel to learn about Charleston’s role in U.S. military history with a former Marine who is also a Civil War historian and graduate of The Citadel. 

Alternatively, bike the new hipster corridor, meeting some of the city’s most talented artisans, chefs, artists and designers side-by-side with the editor of Charleston’s progressive arts and culture magazine.

Enjoy dinner at Husk, set in a beautifully restored Queen Anne house in the city center. Chef Sean Brock scrupulously sources ingredients to ensure their Southern pedigree. Brock changes the menu to reflect seasonal availability, but look for starters such as a tasting plate of fine Southern hams with house-made beer mustard, or pan-roasted scallops with bacon-braised cabbage and grilled peaches, all with sorghum mustard. Main courses might include tilefish with a gold rice risotto, grilled heirloom squash and broccoli greens with citrus butter; or a Wagyu sirloin with oyster mushrooms, creamed spinach and marrow jus.

Fort Sumter
Fort Sumter

Day 4 - 5 : Kiawah Island Overnight

Early this morning, you will have a private transfer to Kiawah Island for an overnight stay at The Sanctuary at Kiawah Island Golf Resort.

Spend a few hours at the Tommy Cuthbert Golf Learning Center, where you can take part in a private lesson. Whether you’re a scratch golfer or a beginner, this is one of the best places to play. Alternatively, you can relax on the beach or even enjoy the resort's spa services. 

This evening, enjoy dinner at either Ocean Room, the resort's prestigious formal steakhouse, or Jasmine Porch, which serves traditional Lowcountry-style seafood with sweeping views of the Atlantic.

The next morning, take a private transfer back to the Charleston airport for departure or return to Charleston to continue your journey.

Clubhouse at The Sanctuary at Kiawah Island Golf Resort
Tricolored heron at The Sanctuary at Kiawah Island Golf Resort
The Sanctuary at Kiawah Island Golf Resort

This beautifully appointed resort is set along a 10-mile beach on private Kiawah Island. 


Book This Itinerary

Contact a travel advisor to book your custom itinerary. Fill out the form or call (630) 734-4610.