The Perfect Three Day Itinerary in Charleson

Aug 28, 2022 | Travel

Charleston is a quaint, historical, sea-side town that also happens to be a food lover’s paradise.

Why I Went: Post-wedding mini-moon!

What I was Surprised By: Charleston is much smaller than I expected. There are fewer areas to walk than I expecting, and I found myself back on King St. many times (shops during the day, oysters for happy hour, then again for dinner and drinks). It’s easy to cover your bases in 2-3 days, so it makes a great spot for a low-key weekend trip.

Who It’s Great For:

  • Solo travel
  • Couples
  • Foodies!


If it has a ✨ emoji beside it, that means I went there myself. Everything else was on my well-researched ‘must-hit’ list when planning, but alas, I couldn’t go everywhere!

If there’s a 🤍 emoji beside it, that means I loved this spot and would return.

If there’s a 🌼 emoji beside it, that means it’s worth going once, but I likely wouldn’t return if you’ve already been (or if you’re hesitant about it anyway).

I don’t share anything on Middle of Somewhere that I personally wouldn’t recommend going to.

Why You Should Go

Victorian Homes Charleston

Quaint architecture

beautiful victorian homes, colourful siding & lots of detail

💡 Did you know? Charleston has a rule that anything man-made that is over 75 years old cannot be destroyed by man. Be on the lookout for nods to history throughout the city (on King St. you’ll find: five and dime tiles in front of storefronts & an Urban Outfitters that’s housed in an old cinema. On side streets, keep your eye out for tie-up posts and concrete mounting blocks for horses).


American firsts, slave history, and intentional paint choices

💡 Did you know? Charleston is home to many American firsts like the first museum, public college & golf course.

But it is also home to a lot deeper history, like being the slave trade capital of North America and the place (at Fort Stumer) where the first shots of the Civil War were fired from, in 1861. You’ll find many monuments throughout the city that are worth the stop to read.

You’ll find pastel colours everywhere, some of which are wrapped in history, like the Haint Blue on porch ceilings, which was thought to ward off haints, or spirits. The rationale was that it was the same colour as water, which spirits couldn’t travel through.

Culinary City

Top chefs, seafood and lowcountry eats

Charleston is a true foodie destination. Take a peek below for some favourite recommendations on where to eat and drink in Charleston.

Coastal Vibes

Beaches & sea breeze

Charleston is situated on the Atlantic Ocean, which means you’ll catch the sea breeze at The Battery and on rooftop patios, and can escape to beaches with warm waters (in the summer, of course) in just a short 20 minute drive.


Below are a round-up of my favourite places & experiences. Keep scrolling to find more recommendations on where to eat & drink, what to do and where to wander, plus a full itinerary.

1. Tasting Menu & Lobster Rolls

Our two favourite restaurants were Sorghum & Salt (we did a DIY tasting menu) and 167 Raw Oyster Bar (lobster rolls for lunch! 🦞).

2. DIY Walking Tour

The best way to explore a city is by foot. We loved walking this route to get our bearings during our first day in Charleston.

3. Palmetto Carriage Tour

A carriage tour is a great way to explore Charleston on a hot day. We loved riding down the quiet Charleston streets, admiring the beautiful buildings and soaking in the rich history. 

4. Rooftops & Oyster Happy Hour

We stumbled upon a fantastic rooftop terrace (Citrus Club) where we sipped on creative & refreshing cocktails. Afterwards, we headed to Darling Oyster Bar for two dozen oysters. Great back-to-back hits to kick off our evening.

5. Sullivan’s Island

A spontaneous trip to the beach was the perfect way to spend the last morning of our trip. Despite it being incredibly hot, we enjoyed a nice late morning stroll down the beach, dipping our toes into the (surprisingly) warm water, followed by lunch at The Obstinate Daughter.

Charleston Historical Buildings
Sorghum & Salt Charleston

Sorghum & Salt


Charleston is a superb culinary destination, with some of the best chefs and eateries hailing from this small city.

Below are the best places to eat in Charleston.

Sorghum & Salt Charleston

Sorghum & Salt | Farm and sea to table with locally sourced ingredients. Seasonal menu that changes frequently. A variety of plates that are perfect for sharing. This was our favourite dinner in Charleston. Tip: make your own tasting menu, based on your favourite menu options. They do offer a tasting menu, but it’s just a selection of items on their menu (rather than items off-menu). We preferred to pick items that stood out to us, rather than going for the pre-selected options. While the menu will likely be different when you go, our favourites were all of the vegetarian items (they nailed these!), the scallops & gnocchi.✨🤍

Chubby Fish Charleston

Chubby Fish | A sustainable seafood restaurant with a menu that changes daily. I was super excited to check this spot out but we unfortunately didn’t get there early enough to secure a seat – they don’t take reservations and we swung by around 6:30PM, but the only table available was 9:45PM. Probably worth the wait but we were too tired to hold out. Definitely add this spot to your list – the reviews are superb.

Lewis BBQ Charleston

Lewis BBQ | John Lewis opened Lewis BBQ in 2016, after he helped his friends open the much beloved Franklins BBQ and Le Barbecue. He then brought Texas BBQ to Charleston by opening Lewis BBQ, which quickly became known as one of the best barbecue spots in the states. Transparently, it wasn’t our favourite. We’ve eaten our way through BBQ in Austin, Nashville and South Carolina, and while we enjoyed our visit to Lewis BBQ, when we compare it to our fair share of excellent BBQ experiences, it wasn’t a standout (though still solid and worth a visit). (In case you’re wondering, some of our favourites have been brisket from Martin’s in Nashville and the beef rib from Terry Black’s in Austin).

Our favourite items from Lewis’ BBQ were: brisket (be sure to get a mix of lean & fattier pieces), ribs, mac & cheese (a standout) and the green chile corn pudding. The banana pudding was also incredibly delicious. We unfortunately didn’t love the sauces as much as we hoped. But again, nothing wrong with this place – we just didn’t leave thinking it was one of the best we’ve ever been to. ✨🌼

PS another BBQ spot in Charleston that I’ve heard is worth a visit is Rodney Scott’s BBQ. We simply picked Lewis because the Google reviews were a bit higher than Rodney Scott’s. I’d definitely visit one of them while you’re in town, if you like BBQ!

Darling Oyster Bar Charleston

Darling Oyster Bar | A bustling seafood spot with a raw bar and great atmosphere. We sat at the bar and enjoyed oysters, crab cakes, shrimp and hush puppies. The menu is relatively small and the portion sizes vary (we found them to be on the smaller end). Would recommend heading here for happy hour oysters before dinner elsewhere – sit at the bar, and enjoy a dozen or two! Give them a call to confirm what time their happy hour is. ✨🤍

167 Raw Oyster Bar Charleston

167 Raw Oyster Bar | A New England style oyster bar right on King Street. It’s always busy so be ready to put your name down and meander King Street while you wait. Highly recommend a lunch visit – we sat at the bar, enjoyed spicy margaritas, ceviche and shared a lobster roll (they even cut it in half for us and plated it on two plates). ✨🤍

Husk Charleston

Husk | locally sourced Southern dishes served in a restored Victorian-era home. Husk has received many accolades over the years. We went to Husk in Asheville, so opted out of a repeat visit in Charleston, but it’s definitely worth a visit.

Obstinate Daughter

The Obstinate Daughter | A go-to spot on Sullivan’s Island. I’ll flag that the food here was good, but not mind blowing (the shrimp roll was great!), but it’s a great option for a late lunch and a cocktail after a beach morning. The menu has a little something for everyone and the interior is costal cute, and it’s one of the better spots near the beach. ✨🤍

Miller's All Day

Here are a few other spots that were on our list. While we couldn’t visit them this trip, I recommend checking them out (based on my pre-trip research):

  • Leon’s Oyster Bar: Combine oysters, Southern-style seafood & fried chicken, and I’m in!
  • Wild Common: Opt for the tasting menu or sit at the chef’s table
  • The Ordinary: An upscale seafood restaurant housed in a 1920s bank
  • Miller’s All Daythe spot to go for brunch (just be prepared to go early or wait)
Citrus Club Charleston

Citrus Club Rooftop


And of course, in a hot city, you need to cool off with a refreshing drink 🍹 . Here’s where to do just that!

Citrus Club Charleston

Citrus Club: A great rooftop bar at The Dewberry Hotel. Highly recommend for both indoors or outdoors – they have great, creative cocktails, the indoor space is bright and fun and the outdoor terrace is sprawling – the perfect place to rest your feet during a hot afternoon (or to wait out the rainfall, as we did!). ✨🤍

167 Raw Oyster Bar

167 Raw Oyster Bar: Already mentioned above for their lobster rolls, but worth mentioning here as it’s a great place to grab a cocktail (we opted for spicy margaritas) for a pause during your shopping haul on King Street. Sit at their bar or in their back courtyard. ✨🤍

Peninsula Grill Charleston

Peninsula Grill: A great spot for a nightcap and coconut cake. Book a post-dinner reservation in their garden, and order a slice of coconut cake to share. Pair with bubbly for perfection. TIp: be sure to book the garden – the indoors is a little old school stuffy. ✨🤍

Citrus Club Charleston

There are a lot of great breweries and cocktail bars. We were exhausted after our wedding, so didn’t stay out late. However, if we had, we might have ventured to one of these spots:

Breweries: Note: most breweries are a little north of downtown, but they’re just a quick Uber ride away.

Cocktail Bars:

Bridge Charleston

Bridge to Sullivan’s Island


While I admit, my itinerary was mostly focused on enjoying the best culinary delights that Charleston has to offer – we did sneak in a little exploring. Here are the best things to do while you’re in town (other than eating!).

Palmetto Carriage Works

Palmetto Carriage Works: It was so hot when we were in Charleston that one day we opted for a last minute carriage tour. We went with Palmetto – the highest recommended and over 10K reviews – and it did not disappoint. The carriage industry in Charleston is super fascinating in the way it’s regulated. Rather than picking a specific tour, you actually don’t know where you’ll be headed until you’re on the carriage. As the carriage heads to the main streets, it stops at a booth where an attendant pulls out a bingo number that dictates which of the ten routes the operator must take. Our route took us off the beaten path a little bit and we found it to be quite educational – the guide pointed out several interesting historical elements of the city that we might have otherwise missed. Albeit a little pricey, I’d recommend one of the tours if a) it’s hot! or b) you’re interested in history. ✨🤍

Sullivan's Island Charleston

Sullivan’s Island: We didn’t plan an official beach visit, but we decided to pop over to Sullivan’s Island (and the beach) on the Saturday mid-morning before we left the city. Sullivan’s Island is a short drive from downtown (approx. ~15 minutes) and there was plenty of street parking a few blocks from the beach entrances. The sand was incredibly well groomed and the water – in mid July – was the warmest ocean water I’ve felt north of the Caribbean. The beach wasn’t too crowded (a good number of people, but well spaced) and the water wasn’t overly wavy (there were lots of people of all ages were swimming). If we were to return to Charleston, we’d definitely plan a full beach day. Pop over to The Obstinate Daughter for a late-lunch after your beach stroll. ✨🤍

Angel Oak Tree Charleston

Angel Oak Tree: The Angel Oak Tree is called a “Lowcountry Treasure”. It is a whopping 65 feet high with a circumference of 25.5 feet, shading an area of 17,000 square feet! It’s a decent drive out of downtown (~20 minutes each way) and the average person probably spends <20 minutes there, so it could be good to tack onto a visit to something else nearby like Kiawah Beach, Folly Beach or Morris Island. We arrived just before a thunderstorm, so only had about 10 minutes to visit, but we felt it was worth the trip – the tree is quite magnificent. ✨🌼

King St Charleston

Beautiful Shops on King St.


One of my favourite things to do in a new city is to just wander – popping into shops, cafes and restaurants along the way. Or just enjoying the views.

Here were my favourite places to wander in Charleston.

Rainbow Row

DIY Walking Tour | Wander around Charleston following this route to take in some of the beauty and absorb the important history of the city. Alternatively, book a guided walking tour (there are plenty of operators!).

  • Pineapple Fountain: According to Southern legend, sea captains would come home from their voyages and impale a pineapple at the gate of their home, signifying they had returned from sea and was welcoming guests into their home
  • Slave Auction Site Memorial: In addition to the Museum (below), the memorial is worth a stop to read the simple but profound sign to learn a small piece about the incredibly sad history of the United States in the 1800s.
  • Rainbow Row: Thirteen colourful historic houses in Charleston, South Carolina. The houses are located north of Tradd St. and south of Elliott St. on East Bay Street (79 to 107 East Bay Street).
  • The Battery: A seawall and promenade at the edge of Charleston, named after a civil-war coastal defense artillery battery at the site. Tip: extend your walk along S Battery St to see some prominent homes.
  • Heyward-Washington House: A historic house museum at 87 Church Street. Built in 1772, it was home to Thomas Heyward, Jr., a signer of the United States Declaration of Independence, and was where George Washington stayed during his 1791 visit to the city.
  • Four Corners of the Law: A city intersection (at Broad and Meeting St) where 4 historic buildings meet. You’ll find federal, state, local & religious institutions, dubed the “four corners of the law”.
  • Old Slave Mart Museum: The Old Slave Mart once housed a slave auction gallery before the American Civil War. Constructed in 1859, the building is believed to be the last existing slave auction facility in South Carolina.
  • Historic Charleston City Market: This historic market was established in 1790s and extends four city blocks. Most of the market is exposed to the elements, and vendors come and go each day, setting up their stalls from morning until evening.
King St Charleston

King Street: Go for a long walk up or down King Street between Broad and Spring St. At the Broad end, you’ll find boutique shops. Then it transforms into more well known shops (both high-end and mid-market) before turning into restaurants and bars. Stop for lunch at 167 Raw Oyster Bar or happy hour oysters at Darling Oyster Bar.

Keep an eye out for nods to history along the way – including five and dime tiles in front of storefronts and the Urban Outfitters that was built into an old cinema. 


Since I know not everyone is a planner, I’ve done the hard part for you so that you can just pack your bags and enjoy 🧳 ✈️ 👟.

Charleston Historic Homes

Day 1: BBQ & Wandering

🥓 Assuming you arrive mid-day, hungry, head to a BBQ joint for lunch – either Lewis BBQ or Rodney Scott’s BBQ (tip: order in advance for pickup so you don’t have to wait in a huge line!).

🍻 Wash down lunch with a beer from a brewery (tip: Palmetto Brewing Company is a 9 minute walk from Rodney Scott’s BBQ or a 14 minute walk from Lewis BBQ).

🧳 Drop your bags at your hotel, freshen up and put on some walking shoes.

👟 Follow this DIY walking tour (or sign up for a guided walking tour) to burn off some of the BBQ. Be sure to stop and read the plaques along the way and begin to take in the history of the city. Meander through the market stalls at the end. OR Take a Palmetto carriage tour.

🐟 Head to dinner at Sorghum & Salt (book a reso in advance)

🍰 Enjoy a slice of coconut cake and a glass of bubbly at the Peninsula Grill. Book a late night reservation, and be sure to call and ask to be seated in the garden.

Tijon Charleston


☕️ Grab a light breakfast from your hotel, or head to the Market for a biscuit from Callie’s Hot Little Biscuit. (especially if you were a fan of the documentary, How She Rolls! We didn’t love the biscuits, but perhaps we’re just not biscuit people). If you’re like us, head to a coffee shop – like The Daily – for a bite to-go.

🛍 Head over to King Street, starting at Broad, make your way up towards Spring Street. Pop into local shops along the way (you’ll find a number of local boutiques near Broad – everything from clothing to homewares – then you’ll hit bigger chains – like Lululemon, Urban Outfitters and a handful of higher-end stores. At the far end of King St., you’ll find bars and restaurants. 

🦞 When you start to get a little hungry, make your way back down the other side of King St. and put your name on the list at 167 Raw Oyster Bar. Do a little more wandering to pass the time (if it’s hot out or you want to rest your feet, head around the corner to The Black Door Cafe). You’ll receive a text when your table is ready. Once seated, be sure to order the lobster roll!

🍹 If you’ve done enough shopping, walk over to The Dewberry Hotel and head up to the rooftop. Enjoy a cocktail at the Citrus Club terrace (if it’s raining, the indoor space is still worth a visit, though expect a wait as it isn’t very large).

🧖‍♀️ Head back to your hotel during the late afternoon to freshen up before happy hour.

🦪 Enjoy Happy Hour Oyster at the Darling Oyster Bar. Opt to sit at one of the bars instead of a table for the best vibe.

🐡 Pop over to Chubby Fish (ideally before 6:30PM) to put your name on the list for dinner. They don’t take reservations, so be ready to wait. Looking to pass the time? Grab a cocktail at nearby Elliotborough Mini Bar or Vintage Lounge. Alternatively, head back to Darling Oyster Bar for some more shucked goodness.

🍸 Enjoy a night cap at one of the cocktail bars on the way back to your hotel. See above for some recommendations! 

The Obstinate Daughter


🥞 Have a slow breakfast at Miller’s All Day (no reservations, so you’ll have to wait)

🌊 Drive over to Sullivan’s Island for a beach day. Alt: Find a crabbing experience!

🍤 Enjoy a late lunch at The Obstinate Daughter (the shrimp roll is great!)

🏡 Head home

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