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Charleston Travel Guide: The Perfect 3 Day Getaway


Before you dive into all the details of our three days in Charleston, there's a few things you should know about our travel style: I am an explorer and if I had it my way, I would try to see and squeeze in entirely too much into every trip....I always want to see and experience as much as I can in a new place. Brad is the opposite, he feels that a vacation should be slow paced, relaxing, and ideally have no plan or itinerary at all. That said, our trips fall somewhere in the middle so that we both get out of the trip what we hope it will be; we do a little bit of exploring, pick and choose what do see + do, avoid overloading the days {which means having a plan but remaining flexible}, and you can bet if there's a beach nearby, we'll be on it. If that sounds like your kind of trip {or you're just looking for CHS recommendations} this itinerary is for you!


Let me also start by letting you know that this is not the itinerary we arrived to Charleston International Airport with. Through a whole series of unfortunate events, misleading information, and zero hotel availability {the PGA Championship was there that weekend} we found ourselves without a place to stay our first night in Charleston, a traveling first for me....but that's a story for another day. But there are a few things you NEED to know when planning your trip to Charleston:


  1. Research big events happening in or around town the same weekend. If there is something on the calendar, I would suggest picking another weekend. This will allow you more options for places to stay, eat, and visit without needing to have made reservations months in advance.

  2. Lyft and Uber are great options for getting around if you have no plans, schedule, or reservations but they aren't always reliable. If you can, rent a car for the added security of being able to get where you want to go, when you want to go there. We were also told it can be difficult to get a ride from the airport though we didn't have an issue.

  3. If you plan on spending any time at the beach, Mount Pleasant is the place to stay. It's clean, safe, LOTS of things are walkable, and it's an easy 15 minute drive to downtown.

  4. The beaches are VERY strict and will absolutely ticket you. Turns out, single use containers of any kind are not allowed on at least some of the beaches in SC {including Sullivans Island} and the signage informing you of these rules is very easily missed. If you plan on spending a lot of time at the beach, I would bring along your favorite tumbler or insulated water bottle on your trip.

  5. It is the South so a number of things are closed on Sundays/Mondays...I personally found that Monday was the day most things were closed and planned accordingly.


Day1: We arrived late Saturday evening so Sunday was our first full day in Charleston. Because of the hotel debacle, we spent the first part of the day getting checked into our AirBnB, getting changed, and exploring downtown.


{Where we stayed:} I can't say enough about our Mount Pleasant AirBnB. The owner, Laurie was SO incredible to work with and so understanding. When I explained the whole situation, she let us check in early which really saved our first day. If you choose to stay in an AirBnb vs hotel, I suggest getting in contact with he owner early to see if there is any flexibility for check-in, check out. Since we didn't have a rental car (the prices right now are just INSANE), we had no where to put our luggage until checking into the AirBnB...also something to consider on the backend or your trip. If you plan on flying out well past check-out, make sure you have a plan for where to store your luggage.



{What we did:} Once settled, we headed downtown for some sight seeing. We started at the Charleston City Market which is a great spot to shop for gifts and souvenirs and see lots of locally made goods. If you're limited on time, I will be honest in saying I think this spot can be skipped. There are some really fun vendors and we did buy a few things but we only spent maybe an hour here although it is a great central location downtown!




Next we headed just a few blocks away to get some pictures in on Rainbow Row. One of Charleston most popular spots, I would suggest trying to get there first thing in the morning to avoid the crowds and walking tours that come through.



From Rainbow Row, we took an adorable cobble stone side street to walk along Ravenel Waterfront Park, where you can see the famous Pineapple Fountain. Tn we headed to King St for a little bit of shopping before headed back to our AirBnB to change for dinner. King St is definitely the place to find some great local boutiques and gifts but the far end is more of an outdoor mall that has shops you have at home. If you have specific places in mind, I'd head there first and be sure to check the hours, most closed by 5 on Sunday. A few of the boutiques I loved or hoped to shop included:

  • Lake Pajamas

  • Madison Matthews

  • Roller Rabbit

  • Spartina 449

  • Shirtini

  • Candlefish

{Where we ate:} Almost any blog you read about Charleston will tell you about Callie's Hot Little Biscuits. Truthfully, I'm not head over heals for biscuits like some so we didn't initially plan on going here but do yourself a favor and pick up a biscuit sandwich from Callie's while you're in town...might I suggest the Fried Chicken biscuit! {truly one of the best things I've eaten} There's a location within the City Market and the original location is located on King's St.


Before heading back to change for dinner, we stopped into Jeni's Splendid Ice Cream on King St which was a welcomed cool sweet treat to escape the heat and wait for our ride.


This was also the only day that I made dinner reservations for a belated Anniversary dinner. After vetting several menus, I decided on Magnolia's and it did not disappoint. As one of our Uber drivers put it, Magnolia's has been here for a long time and there's a good reason why. I had the crab cakes with succotash and brad had the lowcountry bouillabaisse and we both started with a bowl of the blue crab bisque....everything was DELICIOUS! Right in the heart of downtown, it was the perfect spot for our first night dinner. If there are certain restaurants that you have your heart set on, I would absolutely suggest making reservations at least a week in advance.




Day 2: Our second day in town was always going to be a beach day but we had a decision to make: Folly Beach or Sullivans Island. After talking with some of our Uber drivers, we ultimately settled on Sullivan's Island. It was closer to where we were staying and we were told it was less of a touristy spot. If we had more time, I would have loved to spend a day at each but we really enjoyed Sullivans Island.


{What we did:} Prior to heading to the beach, we grabbed some coffee from a great little spot a 10 minute walk from our AirBnB called Brown Fox Coffee. We gathered our stuff for the beach and walked across the street to Mozzo Deli where we ordered sandwiches and drinks to take with us. {Reminder: we learned the next day that single use plastic is not allowed on Sulivans Island Beach and we got really lucky that no one patrolled the beach our first day there}.



We grabbed an Uber from the deli and headed to Sullivans Island....each beach outlet is assigned a station number if you're looking to enter a destination for directions however the length of the beach is walkable so any station will get you to the water. I bought these turkish beach towels just a few days before our trip and they were SO handy for being able to set up a spot on the beach. Unlike some other beaches, there weren't a bunch of shops to buy what you might need for the beach so I would bring what you need with you, this is definitely more of a local spot. It was windy by the water but honestly it was so warm that the breeze was welcome and if you set up nearer to the water, you can avoid getting pelted by sand.



{Where we ate:} Our sandwiches from Mozzo Deli were delish and so fresh! Definitely a great spot for a beach day food.


After spending all day at the beach, our plan was to change and grab pre dinner drinks at a spot I was dying to visit and then find a different location for dinner but we ended up spending our whole evening at Post House Inn and it was my favorite evening of the trip. Even better, turns out Post House was a very easy walk from our AirBnB. Though I do suggest having reservations for a popular spot like Post House, we were really fortunate to snag a table on their beautiful patio after about a 45 minute wait which allowed us some time to walk down to the water to catch sunset and explore some of the BEAUTIFUL surrounding neighborhood.



Day 3: My goal of our last day was to get in any thing we weren't able to on the other days and end it at the beach. I intentionally booked us the latest flight home so that we could get the most of our final day.


{What we did:} We started the day by headed back downtown to grab some final souvenirs and do a little more exploring. There are so many incredible streets to walk down and I wanted to see as much as I could. If your time is limited, I would definitely suggest walking Meeting St towards Oyster Point. Another great spot for some beautiful, historic homes is the area surrounding the corner of Church and Broad streets. I had hoped to get a little more King St shopping in but ended up skipping it in order to get to spend our last few hours at the beach. The other spot I had really hoped to explore was Colonial Lake. This time of year the Peggy Martin Roses are in bloom and grown up the palm trees that line the lake...just a reason to go back!



We headed back to Sullivan's Island for our last couple of hours before heading to the airport which was wonderful however, we spent 45 minutes waiting for an Uber or Lyft to pick us up. Thankfully, we left the beach 30 minutes earlier than we initially planned but I would suggest allowing yourself a cushion to get back from the beach as rides were harder to come by once on Sullivans Island.


{Where we ate:} Before heading downtown we walked from the AirBnB to another great coffee spot called Vintage Coffee Cafe to grab coffee and breakfast and it was just the right amount to fill us up for the day. We had hoped to grab one more local meal before heading to the airport {some of Charleston's most recommended restaurants are located at the main Sullivans Beach entrance: Poe's Tavern, Obstinate Daughter, and Mex 1} but we opted to head for the airport instead after struggling to find a ride from the beach.



I highly recommend ending your trip at the beach...it was the perfect way to try to bring a little bit of the relaxation home.


Next time we visit Charleston, I'd love to have maybe 1 or 2 additional days but there is so much you can see and experience in 3 days time and we truly had such a wonderful visit to the Holy City.



Welcome to Funny Little Fairytale! FLF is our way of sharing our day to day adventures. The new chapters and challenges of doing life together. Here, we hope to create a place to share our favorite places, adventures, eats, drinks, and ideas. FLF is a new journey for us. We want to make this a place where you can learn and share. We hope you enjoy!!

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