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How To Spend A Long Weekend In Charleston, SC

Charleston, South Carolina is located on the Atlantic Ocean and the city center sits on a peninsula.  Founded in 1670, it has retained much of its old-world charm with colorful buildings, French style architecture, and cobblestoned streets.  The city is diverse but it is clear that the touristic areas are white washed and may not exactly reflect the true culture and identity of the town.

For the first long weekend of 2022, I decided to go to Charleston with my mom.  It was my first flight since August 2021 and my mom’s first flight since before the pandemic.  Needless to say, we were very excited to travel together again and explore this historic town.

Let’s talk about the steps to plan this trip and some fun things to do in Charleston if you get the chance to go.

Flights

The first step to travel planning to save money is: be flexible.  So, I was open to going anywhere (even if I couldn’t be flexible with my dates). This allowed me to have more opportunities to find a flight that didn’t break the bank. If I had been set on one destination with specific dates, the chances of finding cheap flights would have been severely reduced.

Another travel planning tip is to get creative.  I live just south of Boston Logan, a major international airport with flights to just about anywhere.  There is a much smaller airport less than an hour from where I live, TF Green Airport in Warwick, Rhode Island.  When I compared flight options to Charleston from both airports, I saw that a direct flight to Charleston out of Boston Logan was $200 more expensive than out of Warwick TF Greene.  It was a no brainer! 

The next creative question was: How can I get to the airport? Uber? Train? Drive?  After pre-reserving parking, I was able to secure a reservation for $45 for the ENTIRE weekend, less than a round trip Uber to Boston Logan and about 80% cheaper than taking an hour long Uber to Warwick.  

Lodging

Once the flights are locked in, it’s time to start looking for where to stay.  Hotels can be expensive in Charleston, so it took a while to find one that wasn’t extremely pricey, had the proper amenities, and was centrally located.  

Landing at 9pm on Friday, it didn’t make sense to pay for a more expensive hotel just to sleep off the airport exhaustion, so we used my brother’s Marriott discount to spend one night in a hotel outside of the city center.  We paid $50 for one night! I don’t like chain hotels, but it was worth it just to sleep and we headed to the city center the next morning.

Our main hotel was an absolute gem that I found on Booking.com called Meeting Street Inn.  Centrally located, old school Charleston vibes, amazing staff, and a happy hour with wine and cheese. SOLD!  The atmosphere was welcoming, warm, and authentic.  We paid $140 a night per person and next time we can book directly with the hotel and save a few more dollars.  While the price tag is hefty, this is the normal going rate for the city center and also considering that it was the long weekend Martin Luther King Jr. holiday.

Restaurants

Food is the number one thing when traveling (at least for me LOL).  We can nourish ourselves and also get a sense for the destination’s culture and vibe through food.  So, it is important to scope out places before you arrive so that you can be prepared to eat authentic, local food.

First, check out Google Maps, zoom in to your destination, and type “restaurants” in the search bar or click the “restaurants” button.  This will populate the map with tons of local restaurants and will show the guest ratings and price range of each establishment.

Next, join some Facebook travel and destination-specific groups and make a post asking about local dishes and restaurants.  This is especially useful if you have any dietary restrictions.  Make sure you are giving yourself opportunities to survey locals about where and what to eat. If you don’t want to make your own post, use the search bar in the group and type in keywords so you can scan past posts for where to eat.

Finally, and this is the most important…ask locals when you get there! I asked Uber drivers and hotel staff where to eat.  After researching online before my arrival, I was pleased to find out that locals recommended many of the places that I already had on my list.  Here is where we ate:

Slightly North of Broad
SO excited for our first Charleston meal of the trip

A local staple run by the Hall family who has multiple restaurants across the city.  Simple, southern food with a European flare.  We started off with a southern charcuterie of patés and picked veggies as well as a butternut squash soup and a lima bean soup.  I got the shrimp and grits and my mom got the fried chicken livers.

Brown Dog Deli

A casual diner-style establishment that serves up comfort food in the form of sandwiches, wraps, and the best side of macaroni salad I’ve ever had.  I got the short rib grilled cheese and my mom got the chipotle chicken pita wrap.

Ever had brunch in a church?  This once church turned restaurant serves up some amazing food and has a killer brunch.The atmosphere and ambiance are unbeatable as you eat your meal beside a stained glass window.  I got the southern breakfast and my mom got the salmon toast.

Carmella’s

This place will satisfy your late night sweet tooth.  Open until 1am, Carmella’s is a family run bakery that serves personal pizzas, cakes, cookies, alcohol, and more.  Be prepared to wait in line, the wait is worth it.  I went IN and got a rose, turtle cheesecake, and cortado coffee.  No regrets.

Harken Café

A cute cafe with good coffee and small treats.  We passed through for a midday caffeine injection and were not disappointed with our latte, cappuccino, spice cake, and cookie.

Church and Union

Ever had brunch in a church? We did! This unique dining experience is something I’d never encountered in previous travels. The atmosphere and ambiance were amazing, literally enjoying your meal under arched ceilings and stained glass windows. I had to partake in a mimosa flight and I ordered the southern breakfast.

Activities

For just a long weekend, we decided to not jam pack the itinerary with tours and museum visits.  Instead, we outlined what we might want to do and chose things based on convenience and availability.  Make time to wander and find the magic of your destination instead of always being on the go and on a tight schedule.  My one regret is not being able to take a Gullah tour because there were none available for that weekend.  Well, it’s just an excuse to go back!

Here’s what we did get into:

Charleston Historic Market

This enormous semi-outdoor market was established in 1788.  It boasts endless stands of local art, artisan work, as well as some corny touristy trinkets.

Gibbes Art Museum

This museum is a small, 2 floor museum that houses rotating exhibits, local art, and a nice surprise of a few works by Renoir and Degas. 

Old Slave Mart Museum

This museum is on the site of the largest slave market in South Carolina dating back to the 1800s for the domestic slave trade.  It is important to learn about this complex and haunting history.

Pineapple Fountain

Head to Joe Riley Waterfront Park  for this cute photo opp and seas views!

Rainbow Row

Check out these amazing pastel colored houses that date back to 1740 as homes of merchants on East Bay Street.

Philadelphia Alley

A quiet one-block long alley between Cumberland Street and Queen Street. with a history of duels, fires, and cobblestoned streets.

Overall, I really enjoyed the vibe and energy of Charleston and I will definitely be back to explore it more deeply.  Would you go? Let me know in the comments!

Want me to help plan your trip to Charleston? Click here!

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