When we moved back to Toronto after living abroad for a number of years, I was determined to keep travel a priority and a big part of our life. Z and I both really value and love to travel, and of course, it was a lot easier to get around while living in Hong Kong and Germany. Both are major gateways to exploring the rest of Asia and Europe. So when Z had a Friday & Monday off work in November, I started researching places we could go. We landed on Charleston because flights from Toronto were inexpensive, it’s a beautiful city with a large (and incredibly preserved) historic district, a vibrant food scene, a huge history to dive into, and a big one for us Canadians – it’s warm and sunny!
The first thing we did when we landed in Charleston was rent a car and drive straight to Sullivan’s Island. Being in the midst of wedding planning and all the stress that goes with it, I really wanted to dip my toes in the ocean and go for a long walk along the beach. But first, we needed lunch! We went to The Obstinate Daughter and decided to share a bunch of plates. Everything we had was delicious, we left totally satisfied and pleased that our first venture into Charleston’s food scene was such a success. From the restaurant, we walked down to the beach along a boardwalk through the sand dunes until we hit the water. I was totally in awe of the pink grass, which I later learned is called pink muhly grass. This feathery pink grass is only in bloom in the late fall, so I was super pleased we came at the right time to see it. We went for a leisurely stroll down the beach along the water, laughing at the sandpipers and how they reminded us of our dog Bao, with their fast little legs! I dipped my toes in the ocean and felt the stress of wedding planning plus the early morning of traveling (we had been up since 3 am!) wash away from me. If you go to Charleston, I definitely recommend hitting the beach first. It’s a great way to decompress!
We didn’t have dinner reservations for Friday night which in Charleston is a big mistake! We had a couple of places we knew only accepted walk-ins and thought we would show up and maybe wait an hour at the bar. We showed up to one at 7:30 pm and there was a 3-hour wait! So we went to the only place that could seat us, Bin 152 which is actually more of a wine bar than a restaurant. They only have charcuterie, but it hit the spot for us!
We stayed at the Emeline, a boutique hotel in downtown Charleston. We loved this hotel for so many reasons. The decor is very art-deco and Z particularly was a big fan of it. And the location couldn’t have been better. Another plus was Clerks Coffee, which is located on the ground floor of the hotel. It’s a great cafe to get some work done in the early morning or grab a coffee on your way out (their coffee is really good!).
We began our second day in Charleston with a coffee-to-go from Clerks and set out on a little self-guided walking tour of downtown Charleston. The walking tour we did was roughly 3 km (that’s just under 2 miles for you Americans), and it was a great way for us to begin exploring Charleston’s historic district.
Self-Guided Walking Tour
We started at Waterfront Park, whose pier juts out into the harbor, to scope out the original Colonial city wall. Then we made our way up to East Bay Street and headed south to see Rainbow Row, a row of historic homes painted beautiful pastel colors. We continued walking south along The Battery, with an ocean view on one side and stately antebellum homes on the other. We continued south to White Point Gardens, where we ogled over the giant live oaks with Spanish moss hanging off the branches. We walked west along South Battery until we got to Legare Street, and walked north up Legare. This street has the best vantage points of what are arguably Charleston’s most beautiful homes, and we loved taking our time on Legare admiring them all. I recommend ending your walk at 167 Raw Oyster Bar on King Street for lunch. Try to get there at least 15 minutes before they open, and be prepared to wait in line anyways – but it is so worth it!
I really adore the old homes in Charleston, and how well they have been restored. I was particularly in awe of the gas street lights some homeowners have brought back. I see a few of these in Cabbagetown where we live in Toronto, and seeing them all over Charleston made me really want to start looking into this as a next house project for us!
As I previously mentioned, we timed our walk to finish around 11 am so we could go to 167 Raw Oyster Bar for an early lunch (the restaurant we tried to go to the previous night, which had a 3-hour wait!). We arrived at 10:45 am and there was already a line down the block! We were even more determined now so got in line. Luckily when they opened at 11, they still had space for us and we only had to wait 15 minutes after that while they seated everyone. So we spent a total of 30 minutes waiting, and it was absolutely freaking worth it. Oh my god, the food here is SO good! We totally understood why there was a line down the block. It was hands down our favorite meal in Charleston. We ordered oysters and the coconut crab dip to start, which was insanely good. For our mains, we shared the swordfish pastrami sandwich and fried oyster po’boy. Everything was out of this world delicious, I’m having trouble finding words to relay just how good it was. You just need to go there and see for yourself!
It was really important to us that we get out of Charleston and tour some plantations. There are many to choose from but because we were only there for a long weekend, we decided on two after talking with some friends and doing our own research. The first plantation we toured was Middleton Place, also home to America’s oldest landscaped gardens. I have to be honest, we were pretty disappointed, and also incredulous and shocked at some points, by the lack of slave history presented here. The original home was burned at the end of the civil war and only a small wing was left which has been heavily restored, so we found the house itself to be a little underwhelming. However, the grounds and gardens were beautiful. We came at a time of year where not much was in bloom but we still enjoyed strolling through the vast property and gardens. I can only imagine the splendor of this place when things are in bloom!
After the plantation, we went back to our hotel for a quick nap and then headed out to dinner at Chez Nous, a highly rated and recommended French restaurant. Tucked down a side alley in a narrow antebellum home, the setting of Chez Nous is incredibly intimate. The menu changes daily and the options are few – two appetizers, two mains, and two desserts. This worked well for us because between the two of us, we were able to try the whole menu. We thought the food here was really very good, but there was no “wow” factor. All in all, we had a lovely and romantic dinner here.
Our third day started with another breakfast at Clerks Coffee before we hit the road and headed to our second plantation, Drayton Hall, the oldest unrestored plantation house in America that’s open to the public (all the other plantation houses in this area were burned down at the end of the civil war). We really enjoyed our visit here and it was our favorite of the two as we found it much more informative and upfront about the slave history. Make sure to do the free audio tour (bring headphones!) to learn about the slave history at this plantation. From a strictly architectural perspective, I also really loved the house itself and how it was preserved instead of restored.
When we finished touring Drayton Hall we popped back into Charleston to meet some friends for brunch at Post House Inn. This was actually one of the hotels I looked into staying at, so I was really excited to check it out and eat at their restaurant. The neighborhood is oh-so-charming, in that classic American way, and the Post House Inn is a neighborhood favorite. The brunch was amazing and the restaurant itself is bright and beautiful. Next time we’re back in Charleston, I want to come back here for dinner.
After lunch, we headed back out of the city to Cypress Gardens. The centerpiece of the garden is the 80-acre blackwater cypress swamp. We rented a rowboat and made our way through the swamp, quietly rowing between the towering cypress trees. I never knew a swamp could be so beautiful, and it was really romantic. The romantic aspect might have something to do with the fact that The Notebook was filmed here (if you’ve seen the movie, you know the scene!), but it really was enchanting. At the end of our leisurely boat ride, we decided to walk the trail surrounding the swamp as I wasn’t quite ready to say goodbye. This was one of my favorite things we did in Charleston and I think it should be at the top of everyone’s list.
Our third day was an adventure-packed day for us and we kept the momentum going by heading to Pitt Street Bridge for a sunset walk. Once an old trolley bridge, it’s now a linear park. We walked along the grassy park lined with palm trees and marsh on either side. At the end of the park is a wooden bridge that juts out a little bit further where fishermen go to catch crab. The park and bridge offer an amazing view of the sunset, and it’s such a peaceful way to end the day.
For our last dinner in Charleston, we decided to go full-on Southern and booked a table at Husk. What intrigued me about this restaurant (aside from being written up everywhere, from Condé Nast to New York Times) was the focus on local and regional ingredients. The menu here changes regularly based on what’s in season, but it’s classic Southern food. It’s located in a restored Victorian-era home and there is a bar next door in the old carriage house. While we thought this restaurant was a tad overhyped (or potentially gone downhill in the last few years, as our local friends said it has lost its luster and famous chef), we had a really enjoyable meal here and I loved trying Southern dishes I’ve never had before. We really liked the fried chicken starter, and Z’s fried catfish he ordered as his main was great. And you know me, I always appreciate a locally sourced menu.
Our fourth and final day in Charleston began with breakfast at Harken Cafe. We loved this shabby-chic, cozy little cafe. I had the seasonal quiche which was potentially the best quiche I’ve ever had – even Z agreed, and he’s a tough critic! Z made an equally good choice with their homemade biscuit with avocado and egg. The coffee was also great. We took our time here, sitting in a cozy little corner by the window, eating delicious food and sipping multiple coffees.
After breakfast, we walked across the street to Washington Park to meet our tour group. I had heard about Two Sisters Tours while researching the best things to do in Charleston, and this small tour company, run by two seventh-generation Charleston sisters, was highly rated and recommended.
We had Mary Helen as our tour guide (the two sisters don’t tour together but separately – apparently they tried to work together once, but sibling dynamics got in the way, so now they do their own thing! haha) and she was wonderful! The tour was very interesting and informative, and Mary Helen kept us engaged and entertained the entire time. The tour gave an overview of Charleston’s history, culture, architecture, and gardens, spanning the Colonial period to modern-day preservation efforts, and we covered most of the historic part of the city. Mary Helen also answered any questions we had – she was an encyclopedia of Charleston! I would highly recommend this tour, especially if it’s your first time in Charleston or you know very little about the history because it really is fascinating.
After our 2.5-hour walking tour, we were definitely ready for lunch – but first, shopping! While walking north on King Street towards the restaurant we stopped for some shopping and souvenirs along the way. We picked up some classic Charleston souvenirs from Grit & Grace – I got a beautiful oyster ring dish with a butterfly painted on the inside (you know how I adore butterflies), and Z got a pocket square and bow tie – so Charleston! Next, I stopped into LAKE to check out their ultra-soft pajamas that I have heard so much about. I came out with the most gorgeous robe that’s perfect to snuggle into post-bath or shower. I had been looking for something exactly like this for months and was so thrilled to finally find it. Our last stop was Tecovas for cowboy boots! (when in Rome, right?) Z got a really bad-ass pair made of black ostrich leather. Not wanting to be left out, I got myself a waterproof suede pair that I’ve been wearing non-stop in Toronto! It was a great shopping success.
By this point, we were really ready for lunch, and finally made our way to Leon’s, a no-frills kind of place but with award-winning food, serving Southern-style seafood and fried chicken. This place was amazing in every way. We decided to go big for our last meal and ordered raw oysters, grilled oysters, fried chicken, and the fish fry. Everything was so delicious, but the grilled oysters were definitely my favorite! This was our second favorite meal of the trip (the first being 167 Raw Oyster Bar) and I’m so happy we ended the trip on such a high note.
Charleston is definitely a city I hope to visit again soon, as I have a whole other list of restaurants and things to do that we didn’t have time for this trip. I also think it would be a great place to come with kids (particularly if you stayed on Sullivan’s Island), which is something I keep in mind as we start to think about that for ourselves in the not-too-distant future. I do enjoy leaving a city and still wanting more because I like having reasons to come back!
If you’re thinking of heading to Charleston for a long weekend, scroll down to see my 4-day itinerary. This is how I would have organized our trip to make things easier and maximize time, knowing what I do now! xx
Charleston 4-Day Itinerary
Arrive and make sure to rent a car ahead of time – you’ll want to be able to get around quickly and easily.
Head to Sullivan’s Island for lunch at The Obstinate Daughter, and make sure to order the clams!
From the restaurant, head down to the beach for a leisurely stroll through the sand dunes and along the water. If you come in late autumn, look out for the pink muhly grass.
After the beach, drive into downtown Charleston and check into your hotel – I recommend the Emeline.
Relax and get ready for dinner. Make a reservation ahead of time for a Southern meal at Fig. We weren’t able to get in this time, but don’t make our mistake and not make any reservations. Our local friends raved about Fig and said it was their favorite restaurant downtown – they are big foodies and I trust them enough to recommend it here!
Wake up and grab a coffee at Clerks, then head out on a self-guided walking tour.
Self-Guided Walking Tour
Start at Waterfront Park, whose pier juts out into the harbor, to scope out the original Colonial city wall. Then make your way up to East Bay Street and head south to see Rainbow Row, a row of historic homes painted beautiful pastel colors. Continue walking south along The Battery, with an ocean view on one side and stately antebellum homes on the other. Continue on south to White Point Gardens, and ogle over the giant live oaks with Spanish moss hanging off the branches. Walk west along South Battery until you get to Legare Street, and walk north up Legare. This street has the best vantage points of what are arguably Charleston’s most beautiful homes.
I recommend timing your walk to end at 167 Raw Oyster Bar on King Street for an early lunch at 11 am at the latest. At a very leisurely pace, it could take you about 1.5-2 hours. If you can, try to arrive at the restaurant a little early before they open. You will probably have to wait in line, but it is so worth it. Make sure to order the crab dip!
After lunch, hop in the car and head out to Cypress Gardens. Rent a rowboat to paddle through the enchanting swamp amongst towering cypress trees, and walk the trail around it afterward if you still can’t get enough.
Give yourself some time to relax and get ready for dinner, and then head out to either Chez Nous (if you want something romantic and classic) or Maison (if you want something a little more lively and varied) for French food. If dining at Chez Nous, make a reservation at Darling Oyster Bar beforehand for a glass of champagne and oysters.
Today is all about plantation houses. Grab some coffee and maybe a bite to eat again at Clerks and hit the road. Stop at Middleton Place first to see the oldest landscaped gardens in America. After you’ve taken your time admiring the beautiful grounds and gardens, grab a bite to eat at their restaurant.
After lunch, head down the road to Drayton Hall. This is where you’ll learn more about the slave history at the plantations, but make sure to listen to the audio tour that you can access via your phone. This is the oldest unrestored plantation house in America that’s open to the public, and from a strictly architectural perspective, the house itself is beautiful and an incredible relic of history.
Depending on the time, head back to the hotel for a rest, or if it’s nearing sunset, drive to Pitt Street Bridge. This is one of the best spots in Charleston to watch the sunset over the marshes. Afterward, walk to Post House Inn for dinner in their coastal cavern. As always, make sure to make a reservation beforehand.
A little something different to start your day – head to Harken Cafe for breakfast. The food here is delicious, and you have a long walking tour ahead of you so make sure you’re fueled up. Grab a table and savor your food and time in this cozy cafe.
Book a morning walking tour with Two Sisters Tours. The meeting spot is in Washington Park, just down the street from Harken Cafe. Make sure you have comfortable walking shoes and your camera is charged!
After the tour, head north on King Street to Leon’s for lunch. But take your time and do some shopping. I recommend Grit & Grace for souvenirs, LAKE for luxuriously soft pajamas and loungewear (this brand was also founded in the south), and Tecovas for cowboy boots.
Arrive at Leon’s and get ready for some seriously good Southern seafood and chicken, with an emphasis on fried. Make sure to order the grilled oysters!
Leave Charleston with a full belly and properly exhausted from all your exploring! xx