48 Hours in Charleston, South Carolina

Why Charleston? 

Millennials, especially HENRY millennials want experiences over things. This applies to my husband and me. For the past three years, to mark our wedding anniversary, we take a trip in lieu of gifts. Last year, we split a week and a half between Sedona, Arizona and Los Angeles, California. The previous year, we spent a couple days at the Inn at Perry Cabin in Maryland. This year we headed south and spent Labor Day weekend in Charleston, South Carolina! We were lured to the destination by the food scene, luxe accommodations, and the promise of experiencing southern charm! Plus, it’s only a one hour flight from DCA to Charleston. Win, wins all around. 

Keep reading for all the details of our trip and additional resources! I intend to go back one day, so tell me if I am missing anything.  

Day 1

We arrived early Saturday morning and were planning on leaving late Monday evening. As a result of inclement weather, we had to shorten the trip. Despite the inconvenience, we thoroughly enjoyed our adventure. 

We landed around 10 a.m. on Saturday and took a quick twenty minute Uber ride from the Charleston International Airport to our hotel. We stayed at Hotel Bennet, which was love at first sight. It’s modern, chic, and oozing with luxurious and plush finishes (more on this hotel in a different post). 

Girl on the rooftop of Hotel Bennet in Charleston, South Carolina
Rooftop views at Hotel Bennet in Charleston, South Carolina

Breakfast at The Daily 

After freshening up we walked for 15 minutes to The Daily, based on the recommendation of a trusted and discerning friend! According to its website, The Daily is a neighborhood marketplace with fresh foods, beverages and goods sourced from farmers and artisans from the Charleston area. It was the perfect spot to fuel up for the day ahead. The place was bustling with locals, tourists, and people just wanting caffeine.

After this, we did a ton of walking to the places listed below:  

King Street: A scenic walk down King street. Shops and restaurants line either side of this street. It’s comprised of both local stores and national chains like Chipotle and H&M. It is a good walk to get a sense of the lay of the land. Click here for more information on all the stores and restaurants on this bustling street.

Pineapple Fountain: Friends and Pinterest listed this as a must-do. Not much to write other than the fact that it’s a fountain and it’s pretty, so post up and take a picture. Below are mine. More fountain information click here.

The Pineapple Fountain in Charleston, South Carolina
The Pineapple Fountain in Charleston, South Carolina

Rainbow Row: Again, social media made me visit this series of brightly colored houses along the Charleston waterfront. Specifically, Rainbow Row is located on E. Bay Street — a block from Charleston’s waterfront. The colorful homes begin on Tradd Street and go all the way to Elliot Street. During the day it’s filled with couples taking engagement pictures, bachelorette parties, and people that generally want to snap a picture in an Instagram-worthy location. Surprisingly, I get overwhelmed in places like this. I freeze up and creativity evaporates. As a result, I didn’t get any cute pictures here. Below is a shot I took on a street that is NOT rainbow row.

Strolling near Rainbow Row in Charleston, South Carolina

Lunch at Millers All Day. The food was yummy, the service was great, and most importantly, the drinks were so strong. I got very tipsy so watch out lol. Here is the menu so you can fantasize about delicious brunch food.

After all that walking, we took a much needed break at our hotel and napped for too long. 

Dinner – Peninsula Grill  

Peninsula Grill is lauded as one of the crown jewels of the Charleston dining scene. It is a four-diamond and four-star restaurant located in the Planters Inn hotel. As a couple, we revel in fine dining with charming aesthetics. As a result, Peninsula Grill was the perfect pick! Plus, for an anniversary dinner I yearned for a romantic atmosphere and intimate service. The Peninsula Grill did not disappoint! My only regret is not being able to capture pictures that reflected the romance and beauty of the ambiance. 

Day 2

Boone Hall Plantation and Garden

Day two was spent at Boone Hall, a former plantation. I selected Boone Hall because admission comes with a series of tours and educational experiences. Specifically, we were interested in the presentations exploring Gullah Culture, Slave History presentation, and the Black History in America experience. 

It’s hard to describe Boone Hall. The grounds are stunning and several iconic movies were filmed there, including the Notebook. There are fruit and vegetable gardens, a butterfly pavilion, and beautiful flowers everywhere. The Avenue of Oaks is magnificent and pictures do not fully capture its beauty.

Sitting on a oak tree at Boone Hall Plantation in Charleston, South Carolina
Boone Hall Plantation in Charleston, South Carolina
Boone Hall Plantation in Charleston, South Carolina

However, that beauty was marred by its past. As the name indicates, Boone Hall used to be an operational planation with slave labor. Consequently, the row of slave quarters that flank the main house serve as a constant reminder of that fact. Knowing that people like my husband and I likely faced so many horrific incidents on those grounds gave me chills for most of the visit.

Slave cabins at Boone Hall Plantation in Charleston, South Carolina. The cabins contain life size figures, pre-recorded narratives, and audiovisual presentations, in an effort to educate visitors about the arduous life of its inhabitants.
Slave cabins at Boone Hall Plantation in Charleston, South Carolina. The cabins contain life-size figures, pre-recorded narratives, and audiovisual presentations in an effort to educate visitors about the arduous life of its inhabitants.

In terms of logistics, Boone Hall was only a twenty-five minute drive from Hotel Bennet and tickets are $24.00 per person. I purchased our tickets online to save time. 

After this somber experience we headed back to Hotel Bennet to relax and get ready for dinner. 

Dinner – Magnolia’s 

For our last dinner, we selected Magnolia’s. Similar to Peninsula Grill, Magnolia’s is another Charleston local and tourist favorite. Not as fancy as Peninsula Grill, but delicious nonetheless. I was impressed by how accommodating they were to my dietary needs (I am gluten free) and the generous portion sizes. Lastly, for perusing purposes, here is the menu!

Day 3

Our already brief trip to Charleston was cut short by an unanticipated hurricane. As a result, the only activity we were able to do before our departure was go to brunch. Based on the recommendation of several friends, we ended up at Felix. Nicely decorated and posh, Felix temporarily took my mind off the fact that I could not be at Hotel Bennet laying by the luxe pool. 

Felix Cocktails et Cuisine in Charleston, South Carolina. 
Seafood & steak sharing plates inspired by Paris, plus versatile cocktails & wines by the glass.
Felix Cocktails et Cuisine in Charleston, South Carolina.
Seafood & steak sharing plates inspired by Paris, plus versatile cocktails & wines by the glass.
Felix Cocktails et Cuisine in Charleston, South Carolina. 
Seafood & steak sharing plates inspired by Paris, plus versatile cocktails & wines by the glass.
Felix Cocktails et Cuisine in Charleston, South Carolina.
Seafood & steak sharing plates inspired by Paris, plus versatile cocktails & wines by the glass.

Conclusion

Lastly, this trip was successful because I received all the aforementioned recommendations from my friends Purvi, Morgan, and Stephanie! These ladies provided valuable tips, tricks, and food recommendations, thereby significantly reducing my research time. Morgan has a blog and you can find her travel guides to Charleston here.

Let me know if I missed anything! I want this to be a resource for all my wandering friends.


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