Tips for planning the perfect trip to Charleston South Carolina

Have you ever visited a place and instantly fell in love with everything about it? 

Visiting Charleston is absolutely magical, it's like being transported back to a different place and time. Where all the stress from a crazy, chaotic whirlwind of a year (like 2020) melts away and is exchanged for southern charm, sweet tea, a stroll down historic cobblestone streets and an abundance of scenic & memorable locations to visit.

When we arrived in Charleston I could immediately sense myself feeling lighter and more care free while the soothing gentle southern breezes washed over me. I wanted to savor every second of our vacation and for our time in this amazing city to never end. Sadly though, our reality was that we only had 4 days to explore around the city & surrounding areas. We also spent 1 amazing day in Savannah Georgia (you can read about our Georgia adventures in an up coming post! :)) Since we were in the holy city less than a full week we wanted to make sure to maximize our time and squeeze every ounce of fun, exploring and sightseeing as possible.

This post will showcase some of our favorite sights, a short list of what I deem must see locations, activities, and a list of items no trip to Charleston should go without. Hope you enjoy coming along on a tour through this absolutely amazing historic town with lovely, picturesque & stunning scenic locations!  

Charleston has a little bit of something to offer everyone, from early American history, numerous historical locations & architecture, beautiful beaches, delicious southern cuisine to sample, lots of great local & high end shopping, lovely people, nostalgia galore and gorgeous plantations to explore! Walking down the street will offer any visitor to Charleston the opportunity to step back in time and get a glimpse into the past.

Fair warning, if your anything like me, you just may find yourself never wanting to leave! While we were in Charleston we may or may not have looked up the prices of homes in the city...surprisingly some are just a few pennies more than my budget will allow😉😂😂 

For our trip we began planning about 3-4 months in advance. Most of our activities and sights to see was my job to plan & organize. So, I spent hours upon hours researching, mapping things out, making lists and planning what would be our best options & creating a game plan. Having our lists handy when we reached the city made it possible to hit the ground running &  ensured we didn't miss any of the important things!;) 

I created a list of all the major historical sights we wouldn't want to miss & mapped them out using a city map I was able to acquire from the city of Charleston's visitor center (I had them mail it to me before our trip). I would highly recommend visiting their website here:https://www.charlestoncvb.com/itineraries/first-timers-guide/, at the top of the page is a link to request a visitor's guide. I found it really helpful for organizing our activities, as well as it provided some great insights & discounts on some of our activities.🙌

After I made a list of the locations we wanted to see I used the handy map to make a sample itinerary for each day. In them I included all the sights that we would pass along 2-3 different routes, places to stop for meals or beverages, historical information that might be pertinent to the area, tours & activities we may want to partake in and the hours/days they were open & the total cost. I also listed areas where we might want to make use of the free shuttle (to help spare our feet) & a guesstimate on time we could spend at each location/activity. I also guesstimated the time we would need to try to leave each day, so we would have plenty of time to enjoy everything we had on our list for the day. 

~During the planning/prepping stage of our trip we met several times to go over my notes, plans and sample itineraries to help us sort things & decide what was a high priority. That really helped us narrow down our top must see locations & focus on the places & things we really wanted to see to ensure we could fit them all in. 

~We knew we wanted to take several tours as well as visit multiple plantations. Since most of them happen to be conveniently located close together, it made the decision to see them all in one day pretty simple. :)  Mapping out which day would be best to take our tours was really helpful and saved us a lot of time once we arrived. Knowing that we wanted to tour at least a few historical homes & several plantations, we made our list of the ones we wanted to see first and used that to help us determine which day/time to see them (see next post (coming soon!) for tips, pics and info about 4 plantations we visited in Charleston). 

~Lastly, we decided which day would work best for us to travel to Savannah (we only had one day in Savannah & wanted to make sure that we wouldn't miss anything, so we checked days & hours of all the locations we planned to see to ensure nothing would be closed). More about Savannah coming in a future post! :)

❈Items to make sure you pack for your trip to the south:

~Definitely plan to bring several pairs of comfortable walking shoes as you will most likely be walking, A LOT!;) *I brought 2-3 pairs to change/swap throughout the day, generally I swapped when we were at the car. This gave me the chance to change from comfy flats, sandals or a sneaker type shoe. **DON'T do what I did (try to prevent blisters by wrapping toes in blister bandaids. They are NOT meant to prevent apparently, only to cover up a blister AFTER it has happened)..OOPSY, I ended up giving myself really bad blisters, under my pinky toes and therefore making it much harder on myself to manage all of the walking we did. I might have been limping behind part of the time but at least all the amazing sights more than made up for my sore toes!😜

~Pack bandaids and other blister protectors, if you are walking 10k-20k steps a day, your feet will thank you for 1) Packing worn in, comfy shoes & 2) Not making the mistake I did above↑ and waiting until a blister actually forms before covering it with a blister bandaid👣

~Plan for warm, sunny weather with: 1) sunscreen, 2) sunhats & 3) sunnies. Generally the weather in the Spring-Fall is sunny & warm, having these items with you will keep you protected from harmful uv rays &  help you minimize discomfort while out and about. 

~Ladies, I suggest bringing a convertible   ←backpack/purse to provide you with the most comfortable & versatile bag. I'm so glad we all found super cute convertible/backpack purses at TJ Maxx before our trip, they were the perfect bag to carry all of our necessities (sunscreen, sunglasses, light-weight sweater, lipgloss/chapstick, gum, wallet, camera, phone etc.) Our bags all had lots of interior pockets as well as side pockets that fit a water bottle. I would highly recommend looking for a bag with that option, it was perfect to keep my hands free for carrying my phone/camera so I could snap pics to my hearts content as we walked around the city. *Another option for a bag would be a great crossbody bag that has lots of pockets to stash all of your necessities for the day.

~Pack light layers! The weather (at least in the Spring-Fall) can see a wide variety of temps all in one day, so layers will be the key to being prepared! *I suggest a light sweater or jacket that can easily be carried along in your bag or tied around your waste. Also a small/compactable umbrella is a great item to toss into your suitcase to keep you dry if rain is in the forecast. 

~Lastly, I suggest packing an assortment of clothing options depending on the activities you have planned. since we were on a girls trip we color coordinated a few of our options and all planned to bring a dress or 2. Not only will that have you prepared if you decide to go to a fancy restaurant or out for drinks, but they are the perfect go to outfit if you plan to tour some plantations or historic homes while in Charleston area. Another plus, dresses are the perfect outfit choice to help beat the heat on a humid/hot day & are the perfect choice to make you feel like a true southern lady!;)

❋Here is a break down of what we did, saw, a few tips of how we organized our activities & mapped out which things to do etc. 

When we travel, we like to get an early start, so we began each day at 6 am. Ate the free breakfast provided by our hotel or at Starbucks and were out the door by 7:30-8am. If you happen to be visiting the holy city from the West Coast like us, this may be a bit harder for you to do.. (it was a 3am wake up time, but to us it was completely worth it!). I'll leave it up to you to decide how much you want to squeeze into your days.;)

Our very first stop was the famous →  "Pineapple" water fountain, that is located in Waterfront park near Gillion St. Stopping here first thing on the morning of our first day was perfect, because later in the day (we walked back along the waterfront in the afternoon) the fountain was packed. Luckily, since we arrived early in the day only a few locals & their little kiddos were there enjoying the coolness of the morning & having fun splashing in the fountain. It was wonderful to not have a crowd and we were able to truly appreciate the beauty of the park, the fountain and take as many photos as we pleased. I would recommend heading here as one of your first stops, between 8am-9am to guarantee less crowds & better lighting for photos. Also could be lovely at sunrise or sunset, but you may have more of a crowd at the end of the day. If it's important to you to see this beautiful fountain, I'd strongly recommend putting this as the first stop of your day and getting there as early in the day as you can to avoid it being crowded.

🍍 *Fun Fact: Did you know that pineapples can be found all over the city? Most people know about the famous pineapple water fountain located at waterfront park and have it as a must see destination (we did too, it is such a lovely place to take a few photos or wade your feet in the cool water on a hot day), but not many know that a pineapple is considered to be a symbol that represents a warm southern welcome, celebration and southern hospitality. We had a lot of fun spotting pineapples all over the city on: wrought iron gates, metal, ornate sculptures adorning pathways & decor while we were out and about. It could make a fun game for kiddos to keep them busy seeing who can spot the most! :)

After the fountain, our next stop was one of the most iconic locations in the city, historic Rainbow Row. It really is as beautiful as it looks in photos, truly one of the most lovely & picturesque places in the city.

 All the photos I took with my smart phone look like they could be a postcard!;) We lucked out here as well and had the street to ourselves for a good half hour before anyone else showed up. It was the perfect opportunity to snap photos and spend some time reading their signage that indicate how old/when the buildings were restored/preserved, how they were used and other interesting tidbits.  

We wanted to explore all the historic areas south of Broad so we spent some time zig-zagging our way around, making sure to walk down several of the cobblestone streets & stopping to smell the roses, breathe in the fresh floral scents & take our time to absorb all the natural beauty all around us. Anyone who loves flowers & the dreamy way that moss covered trees sway in the breeze will be enamored by all of the gorgeous plants & nature that abounds everywhere you look (some of the most amazing flower boxes I've ever seen adorn all of the picturesque homes & the most lovely trees dripping with Spanish moss are all over the city😍)!  

❋A few of our recommendations & hidden gems to add to your list:

Cobblestone streets anyone? If you have been dreaming about walking down a beautiful cobblestone street, lined with some of the oldest homes in the city & hearing the sweet sound of a car gradually driving over the cobblestones, then you won't want to miss Chalmers Street. One of the most historic streets in Charleston. At 17 Chalmers Street, can be found "The Pink House" (also an art gallery), known as one of the oldest buildings in the city. The home is the 2nd oldest residence after Colonel William Rhett's home (scroll ↓ to see photos & info from our tour of this amazing home). 

If you love historic homes & cobblestone streets make sure to add Stolls Alley & Longitude lane. Longitude Lane →   happens to be one of the most charming, quaint and somewhat hidden gems in the historic district. It is located between Church and East Bay street and approximately 150 feet North of Stolls Alley (which also happens to be a lovely small historic street). We immediately fell in love with the vast array of scenic views, secret garden like gates & door ways all up and down the lane, and the lovely picture perfect window boxes and shutters. Varying shades of moss, plants, ivy and flowers greet you as you enter the alleyway sheltered by massive oaks above creating the perfect place for a stroll down memory lane. 

Philadelphia Alley is known as the historic location of numerous duels. It can be a bit difficult to find & is bordered by Cumberland St. on the north, State St. on the east, Queen St on the south & Church St. on the west. To find the north end of Philadelphia Alley head to Cumberland St. The south end of the Alley is on Queen St. While inside the alley look for a plaque on the west wall that explains the name of the alley & it's importance. While you're in the area check out the Little Free Library located at 46 State St. (in a pink building) to get yourself a new fun read for your vacation.  

Another little side street or two that are filled with super cute houses and lovely cobblestone roads are S. Adgers Wharf & N. Adgers Wharf which are located off E. Bay St & Concord St. Loads of charm, window boxes filled with flowers, colorful shutters and some of the sweetest doorways & ornate iron work in the city. 

Prices Alley, Bedon's Alley & Horlbeck Alley are all noteworthy as well and worth checking out if you have time in your schedule. I suggest allowing yourself plenty of time to leisurely meander down each of these beautiful alley's and to stop and smell all the roses along the way. 

You never know what secret garden, beautiful doorway, ornate ironwork, stunning flower or window box, glorious old home, gorgeous trees covered in moss or horse drawn carriage you may discover while exploring around the holy city. That is why I suggest planning to do a lot of walking and even attempting to create your own walking tour. What better way to fully grasp the sights, sounds, smells and the lay of the land than to put your feet to the pavement? It truly is the best way to see & experience the best of what Charleston has to offer. No other option puts you completely in the drivers seat or allows for freedom and flexibility quite like a personalized walking tour that you create yourself. 

Thankfully, the city is laid out pretty well and actually, it's rather simple to figure out. With our map of the city, our list of must see sights & a little planning ahead we were able to see everything on our list while still having plenty of time to wander up and down any street or alleyway that caught our eye & of course having lots and lots of time to stop for photos!;)  

←This is a photo of our route we took on our first day (in purple) and some of the sights we walked to on our last full day (in blue). I love that this map highlights most of the historic homes, churches, and major points of interest. Carrying it with us as we walked enabled us to confidently explore the city on our own & made sure we found everything we wanted to see. 

If you love historic churches as much as we do then you'll definitely want to walk down Church Street, Meeting Street & Broad St. This is where you'll find some of the oldest churches in the city dating back to the 1700's. One of our favorite churches, St. Michaels Episcopal Church is one of the oldest surviving religious structures in Charleston. It was built in the 1750's & is where George Washington worshiped on his tour through the holy city in 1791. He sat in pew 43 which is now known as the "Presidents Pew" and has since been used by General Robert E. Lee, President Bush, other Presidents and dignitaries when they visit Charleston. The pew is still used any time the church is filled on a Sunday, if you happen to be visiting during a service you may just have the opportunity to sit here yourself! 

We couldn't help but marvel at all the stunning features inside this beautiful church, from the lovely stained glass, the original John Snetzler Organ (only the case remains from the original that now surrounds a newer Organ added in 1994) and the amazing painted ceiling. There is so much history here as well as an incredible interior, both of which made us fall in awe of this beautiful church. We were amazed at how well kept all of the churches are, especially while inside St. Michaels. Everything was pristine! We were also very impressed by the curvature of the spire and the amazing bell tower at the top (the bells are rung every hour filling the air with their melodic sounds). We also spent a little time walking through the adjacent cemetery where gravestones date back to the early 1700's. 

The soft pale pink hue of the French Huguenot Church makes it really stand apart from the other churches that are more earth toned. We all loved the unique design of the church, we thought it slightly resembled a European Gothic castle. Fans of the reality tv show "Southern Charm" may be interested to know this is the church of Thomas Ravenel.

Located directly across the street is the famous Dock Street Theater which has been in operation for over 200 years! The original structure was built in 1736 and is the first building to be exclusively used for theatrical performances. Further on down the road is St. Philip's Church. The tall round bell tower can be spotted long before the church comes into view. 

If you take a left from here just a short block walk leads you directly to the Circular Congregational Church. This beautiful church has a unique shape and offers a different view point of St. Michaels Episcopal church from a distance. The church was built in 1892 although the congregation has been meeting since 1681 making it one of the oldest continuously worshiping congregations in the south. Due to the history of the church the graveyard is one of the oldest burial grounds and has gravestones that date back to 1695! The round structure & history of the church definitely makes it fascinating to see and fun to capture on camera.:)

One of our favorite churches and top recommendations is the Cathedral of St. John the Baptist. The stunning painted ceiling, high arch ways, painted glass windows, tall bell tower and unique design of the cathedral make this church one of our top recommendations. It is located off Broad St. and super easy to spot with the massive towers that can be spotted well before you are anywhere near the cathedral! Definitely pop by to take a look. It is especially fun to hear the bells ring at the top of the hour :) 

After you get your fill of churches I suggest heading to the City Market to do a little shopping for a souvenir or two from one of the many local artisans or crafters. The market was originally established in the 1790's to allow farmers a place to sell beef as well as produce and has been operating as a continuous series of one story market sheds ever since. We found numerous gifts and souvenirs (if you still have a lot of activities planned or places to walk I suggest going to the market near the end of your day. Due to covid they have reduced hours but I just read that those should be adjusted again soon to provide longer hours.)

While we were shopping for souvenir's in the City Market we bought combo tickets to tour the historic Aiken-Rhett home, the former home of one of Charleston's first Governor's & the Nathaniel Russell historic home, one of the most prominent merchants in Charleston in the 1800's. Both are amazing historic homes that I will divulge more info about in another blog post coming soon!:)

 ❈Food recommendations:

Before we toured the home we stopped for some lunch along king street at the delicious ""Callie's hot little biscuit". Every flavor of their sweet or savory biscuits are mouthwateringly tasty and good to the last crumb! We were so excited to learn that they sell these biscuits in a few locations in Oregon, I can't wait to take my family along with me to try their scrumptious biscuits! My recommendations are the blt biscuit sandwich, and the 3 for $6: cinnamon biscuit, blackberry, and shortcake. If you happen to be a first time customer they also offer a choice of a free biscuit. I chose a savory biscuit, the cheese & chive which made a perfect snack later in the day. We loved all of the biscuits and highly recommend checking them out!

Another fun place to stop for a treat is Belgian Gelato located on Vendue Range near Vendue fountain at Waterfront Park. We all tried the super yummy dutch pancakes (definitely must try these!! Sooo good!) & pistachio gelato in a lavender cone.😍😍 The perfect mid-day snack!

If you are looking to try some southern staples such as fried okra, pimento, fried flounder balls, grilled brussels sprouts, fried green tomatoes or other delicious southern cuisine you must plan a stop at The Glass onion. https://www.ilovetheglassonion.com/

"The Glass Onion is one of Charleston’s original home grown neighborhood-based, locally focused, all natural restaurants" ~ilovetheglassonion.com

Seriously some of the best southern food I've ever tasted, so scrumptious and more than met all of our hopes of tasting genuine southern food. The owner & our server were both extremely helpful in their recommendations and info about Charleston locations we had explored. I suggest trying the fried green tomatoes with pimento & southern mac, both are incredible!😍  We visited The Glass Onion on our last night & it was the perfect end to our day. We enjoyed our delicious meal in their outdoor seating area while we viewed a gorgeous sunset. It was absolutely divine.  

Our favorite place to eat though has to be Miller's All Day, located on King St. & Broad St.. Hands down the best southern style breakfast in the holy city, imo😉 Since we are all Miller's either by blood or marriage this was a must on our places to see & eat. We arrived early (which is highly recommended if you wish to have a table ;)), and were some of the first seated. Quickly afterwards the restaurant was filled with local patrons and other tourists. We were so glad we arrived when we did! 

I ordered the "Millers Plate" (it was all incredibly tasty!) which allowed me to try fresh unicorn grits (red grits, that are lightly salted) for the first time & another version of a southern biscuit. So yummy! While we waited for our order we browsed the fun souvenirs and the fun decor. If you're hoping to try southern grits & looking for a yummy breakfast joint while you're in Charleston, you definitely need to put Millers All Day on your list! Check their yummy dishes here:   https://millersallday.com/pages/menus

❈A few other places to add to your list: A walk along the waterfront near waterfront park is the perfect place to take a photo of the Arthur Ravenel Jr. bridge & an excellent spot to take in the view of the harbor. Perhaps, while relaxing on one of the spacious swinging benches on the boardwalk?! 

If you plan to sit on one of the swings you may need to wait a little, plan to arrive early in the morning or later in the evening after the crowds diminish. In the spring it is such a lovely place to observe the harbor, people watch or to sip on a cold iced tea/lemonade while enjoying a cool breeze. 

Lastly, you definitely  won't want to miss The College of Charleston, especially if you're a "Notebook" film fan. This is another one of the locations used in the film and I could totally see why, the buildings all date back to the 1770's (this is the 13th oldest college in the US. and the oldest college in Charleston). Truly a lovely place to take a stroll or bring a picnic under the giant shaded mossy oaks. 

Also, while you're in the area be sure to check out Folly Beach, Morris Island Lighthouse, The incredible 400+ year old Angel Oak tree, and Cypress Gardens (famous for the boat scene in "The Notebook" film). I will include tips, insights & some of our favorite highlights about these amazing places in a future post coming soon. So be sure to check back often so you don't miss it! :) 

❈For more info, insights, recommendations and tips check out my next post where I share all the best tips about how to see 4 amazing southern plantations in 2 days. *Post coming soon! 

Drayton Hall

Until then, have fun planning your dream trip to Charleston! Let me know if you have any questions that I didn't cover or things you'd like to know about "Drayton Hall", "Middleton Place", "Magnolia" or "Boone Hall" plantations in the comments below so I can include them in my next post :) 

Happy travel planning friends!

                                ~K

*For other recommendations, insights, travel tips, travel & vacation planning, motherhood, homeschooling & all of our adventures checkout my instagram page:  

https://www.instagram.com/thishomeschoolerslife/   

*Also check out my other blog posts in my "Joy of Travel series: 

~Packing Hacks/Tips: 

https://thishomeschoolerslife.blogspot.com/2021/04/packing-hacks-travel-tips-for-whatever.html

~Tips for planning/prepping for an upcoming trip/vacation:

https://thishomeschoolerslife.blogspot.com/2021/04/the-joy-of-travel-how-to-plan-prep-to.html

*Other travel related posts:

~Travel tips for visiting Glacier National Park: 

https://thishomeschoolerslife.blogspot.com/2021/05/travel-tips-for-visiting-glacier.html

~Travel Tips for visiting Yellowstone National Park: 

 https://thishomeschoolerslife.blogspot.com/2021/05/a-compilation-of-best-must-see-places.html & 

https://thishomeschoolerslife.blogspot.com/2021/05/10-tips-to-help-you-plan-perfect-trip.html