Charleston – Fall Weekend Getaway

Overview

Charleston was the perfect girls’ weekend getaway. The fall temperatures were mild, making it an ideal time to visit the charming city. It was a quick and relatively cheap flight away from D.C, thus a very doable weekend trip. 

In the true spirit of a weekend getaway, we flew into Charleston on a Friday night after work and returned first thing Monday morning. Fortunately, that meant we did not have to use any vacation days. Despite the brevity trip, we had 2 full days to enjoy the charming, southern city. We spent most of our time exploring the city on foot. However, we booked a few unique tours and of course explored Charleston’s delicious culinary scene!

Itinerary

Day 1 - Evening Flight to Charleston

Day 2 - Exploring Charleston

    • Charleston’s Historic District
    • Preservation Society’s Fall Tour of Homes
    • Sunset at The Battery
    • Ghost Tour

Day 3 - Exploring Charleston

    • Brunch at Hyman’s and the Charleston City Market
    • Pineapple Fountain
    • Rainbow Row
    • Dinner at Poogan’s Porch

Day 4 - Early Morning Flight Back

Lodging

Detailed Itinerary/Sights

DAY 2: EXPLORING CHARLESTON

After getting some beauty sleep at the Courtyard Charleston Historic District, we kicked off our morning at the weekly Charleston Farmer’s Market in Marion Square. It was conveniently located right by our hotel and had several delicious food options to start the day. 

Charleston’s Historic District

With full stomaches, we enjoyed a 20 minute walk to the heart of Charleston’s Historic District. We spent a few hours getting lost in the old neighborhoods and admiring the beautiful architecture. The small streets south of Broad Street, were especially charming. We passed by the famous Philadelphia Alley and stopped for sweet tea, which the south is known for.

Preservation Society’s Fall Tour of Homes

During our morning walking tour, we picked up our wristbands for the Preservation Society’s Fall Tour of Homes (Charleston’s Architectural Gems Tour, ~$50), which was from 2 - 5 PM. The ticket allowed us to tour 6-7 private homes in Charleston, which are only open to the public 1-2 times per year specifically for these tours. We spent most of the afternoon touring the beautiful homes and marveling at their splendor and history.  

Fall Tour of Homes

Note: There are several tour options that allow you to visit different homes. All of the home tours are self-guided. The Nathaniel Russell House is also a recommended visit, especially if you are in Charleston when these private home tours are not offered.

Sunset at The Battery

Following the tour, we walked around Lower Meeting Street to enjoy more of Charleston’s charming architecture. Right before sunset we headed to The Battery to watch an amazing sunset over the water. 

Sunset at The Battery

We then walked 20 minutes to Fleet Landing for our 7:30 PM reservation at the southern style restaurant located on the waterfront. It was a pleasant walk there, partly along the water. The restaurant was delicious and did not disappoint.

Charleston Ghost Tour

Following dinner, we headed to our 9:30 PM ghost tour with Old Charleston Tours (the tour was $20), which had one of the best ratings. We met the group in Washington Square before heading out. Our animated guide took us on a  90 minute tour of the city, sharing several spooky ghost stories along the way. 

After all the haunting tales, we headed to King Street for a night cap before a well deserved night of sleep. 

DAY 3: EXPLORING CHARLESTON

Brunch at Hyman’s and the Charleston City Market

We kickstarted our day a little later than normal with brunch at Hyman’s Seafood, a well known restaurant in the Historic District. They didn’t accept reservations, so we arrived around 11 AM, when they opened. We enjoyed hushpuppies and other traditional southern food before setting out to the explore for the day.

Our first stop was the Charleston City Market, located in the heart of the Historic District. It had multitudes of artisanal stands. I was very tempted to buy an alpaca bear (they are soo soft!!), but for the sake of my wallet, I refrained. 

Pineapple Fountain

After getting our fill of window shopping, we spent a few hours once again getting lost in the architectural beautiful of Charleston’s old streets. We even walked through a cemetery connected to one of the city's old churches, which was intriguing after the previous night’s ghost tour.

We then headed to Waterfront Park, where the famous Pineapple Fountain is located. Although, it was quite different from the old world charm of the rest of the city, it did provide a good photo op. 

Pineapple Fountain

Rainbow Row

Rainbow Row, with it’s colorful houses, was the next stop on our walking tour. After snapping a few pictures, we continued on our way.

We happened by a quaint street, called Longitude Lane, which was the perfect place for a photo shoot. We took a few photos (some of which were profile picture worthy) before heading back to The Battery. 

Photo Shoot by Longitude Lane

Dinner at Poogan’s Porch

Satisfied with our photo shoot, we went back to The Battery for another idyllic sunset. We then walked to Poogan’s Porch for an amazing, upscale southern dinner. The restaurant had a lot of charm and was even featured on the previous evening’s ghost tour. Luckily, we had no spooky encounters while we were there.

Following dinner, we transferred to the Aloft Charleston Airport Hotel & Convention Center and called it an early night since we had to be up at the crack of dawn for our flights the next morning.

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