Charleston Weekend Itinerary

Head down South to the marshlands where candy-colored architecture meets cobblestone paths and alluring history, delectable food, and refined shopping abound!

That’s right let’s go to Charleston, S.C.!

My girlfriend and I had a little reunion rendezvous a few weekends ago in this most delicious of towns. We shopped, explored, ate, and cheers-ed to our twin hearts’ content, catching up on new plots and reminiscing about forgotten tall tales.

Charleston is always a favorite of mine, and in fact this was my 6th visit to the holy city in the past decade. My husband and I even celebrated wedded bliss there on that thing called a honeymoon.

A couple of you lovely peonies asked me to share my favorite places and things to do, so I thought I would let you in on all the goodies with this Charleston weekend itinerary. Below you’ll find a listing of the very superlative places to eat, drink, shop, stay, and explore…well at least in my humble opinion.

Charleston Weekend Itinerary

Where to Tipple Your Inhibitions

The Gin Joint – Have fun with the bartender’s choice drink and pick two words to describe the type of drink you want then see what the bartender comes up with!

Camellias – a champagne lounge where pink reigns for a true feminine haven!

Pavilion Bar – best rooftop experience.

Vintage Lounge – major Art Deco vibes and you must try the blind taste testing game where the waiter picks your wine and you try to guess what it is. We enjoyed this so much although no one at our table got it right!

Where to Lay Down Some Dough

The Boutique – all the fine china and linens you could dream of!

Beau & Ro – lots and lots and lots of pretty dresses!

Charleston Shoe Co. – really comfortable and chic sandals. I bought two pairs!

Artist Collective, Charleston

Artist Collective Charleston – so many gorgeous and intriguing art works!

Where to Satisfy Your Tastebuds

Husk – great ambiance and delicious food. Don’t miss the Dragoon’s punch cocktail and the smoked fish toast.

Virginia’s on King – I have eaten here every time I’ve been to Charleston in the past decade. It is always yummy, good home style Southern food. Don’t miss the shecrab soup!

The Grocery – this was our first time here, but I will definitely be back again and again. Hands-down it was the best meal at a restaurant I’ve had all year!

Where to Get Lost

Yes, indeed I have visited all of the places below. For a weekend I would choose two, depending on how much time you plan to shop on King Street.

drayton hall front view

Drayton Hall – absolutely gorgeous example of Georgian architecture and the audio tour does a really good job of depicting life for all those on the plantation from the slaves to the white women.

Aiken-Rhett House – fascinating to see the difference between plantation and townhouse.

Middleton Place – the gardens are really lovely! It is also really interesting to learn about the cultivation of rice and see the working forge.

The Old Slave Mart Museum – this one is difficult to tour, but I think it is really important to recognize and learn about Charleston’s history as a major part in the interstate slave trade. Charleston is not just moonlight and magnolias!

St. Philip’s Church & Cemetery – stunning architecture and interesting history, especially for the Southern history buffs. Don’t miss the cemetery and grave yard.

Fort Sumter – it is fascinating to take the ferry out to the fort and see and learn about the official start of the Civil War.

The Gibbes Museum of Art – a fine collection of American art and Southern artists.

Where to Prop Your Weary Feet

Ok, there are a wealth of places to stay in Charleston near all of the action, so you can walk to everything! I have stayed at Charleston Place, The Andrew Pinckney Inn, Elliot House, Embassy Suites in the old Citadel (I wouldn’t stay here again until they renovate the interiors), and Homewood Suites.

My 5 Star choice is The Charleston Place

Elliott House Inn

For quaint atmosphere stay at The Elliott House Inn.

The Bennett Hotel lobby

Where I want to stay next time: Hotel Bennett.

Alright friends – I hope you enjoyed this quick tour around Charleston, S.C.! If you have any questions don’t hesitate to reach out via email or comment below. Happy travels!

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