Destination Delegation: A Girls’ Trip Guide to Charleston

Well it took me about two full days to recover from my two-day trip to Charleston with some of my best girlfriends. That should tell you something about our incredible trip to one of my favorite cities in the south. Let me tell you, it’s been a long time since I’ve laughed so hard that I literally peed in my pants- although it doesn’t take much now that I’ve birthed two children. Anyway, I’m thrilled to share with you my list of our favorite places to eat, shop, sleep and “do,” while visiting Charleston. This “guide” is specifically for a trip with the gals, whether it’s a mother/daughter trip or a getaway with your besties, as I haven’t done much research or personally experienced a trip to Charleston that includes romance or children. However, I do think some of my list would work for families or a significant-other-vacay, such as the restaurants or excursions, but again, it’s mainly geared toward women who want to spend their time in Charleston eating, drinking and buying everything they see. And let me tell you, I’m not sure there’s anything left to buy after we hit-up King Street. If we’re good at one thing, its shopping… well, make that two things… we can also drink you under the table. There were six of us total in our group, and all of us have young children (under the age of six). I thought our number was perfect as we could all fit in one Uber-xl or three pedi-cabs (see below) and could easily get dinner reservations (over six is often hard to book through online reservations). Our group was not too big or too small, which made it easy for us to always have a buddy if everyone didn’t want to do the same activity (though this was rare). There’s enough to do in Charleston to keep you busy, but not so much to see that you feel overwhelmed or obligated to visit every attraction. And even though we did party quite a bit, we came home refreshed and ready to “be mom” again. It was the perfect Friday through Sunday city to visit together.


So without further adieu, my lists are below, along with notes and little tid-bits of advice. *Please note, these are all based on my opinions and experiences on a group-trip and what worked for us. I love a good guide, especially if it comes from someone who shares similar tastes and likes/dislikes. Hopefully you will find this helpful in planning your own girls’ trip to Charleston. I highly recommend it!


Where to Stay

There are SO many beautiful hotels to stay in when visiting Charleston. However, for a girls’ trip, I wanted to find us lodging in a good location (safe), somewhere that offered areas where we could hang-out together outside of our bedrooms, and something that is also a bit luxurious since we rarely get to travel without our families in-tow. After much research, I decided upon 86 Cannon, and we could not have been more impressed with our stay there. Not only is it divinely decorated, but it offers the perfect setting for a group trip, whether that be with spouses or friends. It’s small and almost operates as a bed and breakfast, so it can’t accommodate large groups, but that’s what I love about it. Except for one other couple, we were the only guests on the property, and it felt like we had our own glamorous B&B for the weekend. There are three rooms “stacked” on one another in the main part of the building with two other rooms just off the backside of the former house. The rooms themselves are beautiful and unique and the bathrooms are equally chic. They only offer king beds, which worked well for us (two gals to a room), but it’s something to consider if you prefer separate beds.


Separate from the bedrooms and to be shared by all guests (which again, was basically just our group), is a beautiful all-blue sitting room, a stunning kitchen/dining area and a fun all-red room called the “Honor Bar.” You could use these rooms any time of the day, and if you wanted an alcoholic beverage or any of the offered snacks, you would just fill out a card and then help yourself (hence the name the “Honor Bar”). Included in your room cost is a complimentary breakfast, which was always fresh and delicious, and consisted of coffee, various juices, fruit, granola, yogurt, muffins, pastries, hard-boiled eggs and quiche. Also included is complimentary wine and cheese every evening from 5pm to 6pm. The staff put together a cheese board for us each evening and served us glasses of wine, which was a perfect option for us pre-dinner while we all got ready. It’s not the cheapest hotel option in Charleston by any means, but it’s worth every penny! The service and accommodations are incredible, and again, it was the perfect place for our group to enjoy hanging out together, whether we were all lounging on one of the beautiful outdoor porches in our pajamas drinking coffee, or enjoying a night-cap in the upstairs Honor Bar. Your stay also includes bikes, which we ended up not using, since we loved taking the pedi-cabs (see below). Last note about 86 Cannon: They’re in the middle of renovating the cottage right next door to their property to expand their number of rooms and to put in a pool. I’m very excited about the addition of their pool, and I hope to return next year to enjoy it in person (the expansion should be done by summer 2019). Check them out online, but please note that I was not paid to stay there nor was my stay discounted in any way. I just liked it so much, I wanted to share my experience with you!

Additional Hotel Recommendation Similar to 86 Cannon:

Zero George– Similar B&B feel to 86 Cannon and similar price point (I’ve stayed here too, and it’s amazing)

Charleston Harbor Resort– The first time I visited Charleston on a girls’ trip, we stayed in the city. I had heard about Mt. Pleasant and the resort and that is wasn’t far from downtown at all, but we never ventured there, as I still believed it to be too far to venture out to on a limited stay. However, this last trip proved me wrong. I loved staying at the Charleston Harbor Resort, which is located in Mt. Pleasant next to Sullivan’s Island. It’s a ten-minute drive or water-taxi ride to downtown Charleston, and it offers the best of both worlds in my opinion- beach/pool life and proximity to city life. I loved overlooking the ocean from my hotel room there and the pool and pier are stunning. You get to experience “resort life” with easy access to everything that downtown Charleston offers. I’m a big fan of this place, but be sure that when you book a room here, you book on “The Beach Club” side and not the “Harborside” where the rooms are not nearly as nice.


In fact, we loved our rooms at The Beach Club so much that instead of venturing out for breakfast one morning, we were boujee and “ordered” Callie’s Hot Little Biscuits directly to one of our rooms. Now, this isn’t really an option of course (though they do cater for larger events), and the hotel breakfast was quite nice too (of course I tried that out on your behalf- ha), but for our stay, Callie’s was kind enough to set-up a biscuit bar on our terrace overlooking the water.

Callie’s Hot Little Biscuits has an actual shop in downtown Charleston, that’s a MUST visit, as it’s the original location for the company. You can go for breakfast, lunch or really anytime you’re craving the best biscuit you will ever have. We were treated to a sampling of several of their offerings both savory and sweet, and I’ve yet to eat one I didn’t love. You can also order their biscuits (and other goodies they offer) from their website and they ship frozen directly to your door to simply heat-up and serve at your leisure.

Another fantastic option in Mt. Pleasant is located right around the corner from the resort. If you like the idea staying with all your friends near the water with resort amenities available to you, but maybe prefer a house/cottage, then The Cottages on Charleston Harbor are the perfect fit. You have access to the Beach Club amenities, but you get to stay in a private cottage directly overlooking the water. I will be staying in one of the cottages on my next trip to Charleston, as they looked so dreamy, and I love the idea of all of my friends being in the same house together while on vacation.


Where to Eat

This one is going to be impossible. Charleston offers SO many incredible dining options, and I’m sure that by the time I finish this post, there will already be a new restaurant open that’s the talk of the town. One of the women on our trip is from Charleston, so I did have some insider knowledge when it came to where to eat. I strongly suggest booking all dinner reservations as far in advance as you can since the popular restaurants are booked weeks in advance. You can also make reservations at most lunch spots, but we weren’t exactly sure of our plans during each day, so we didn’t book those ahead of time. We never waited long for lunch, but it wouldn’t hurt to have reservations if you plan your days out so you know you won’t have issues at the popular restaurants that don’t seat many people- like Husk.

Breakfast/Brunch/Lunch Suggestions:

Basic Kitchen *We ate here, and we LOVED it. It’s healthy eating that doesn’t compromise on taste. We all ordered something different, and everything was delicious. A must is their Beet Margarita that tastes divine and was my favorite cocktail from the entire weekend

Husk *Need reservations ahead of time. Amazing burgers. All locally sources ingredients

Miller’s All Day *This is great for breakfast/brunch/lunch. All the food was incredible and the cocktails are fantastic. I had a latte laced with bourbon and caramel and it was delicious. They’re known for their waffles, which are beyond good and are a must-order as well. They do not take reservations, and we had to wait over an hour to be seated, but they’re located on lower King Street, so you can shop while you wait!

The Watch Rooftop Kitchen and Spirits * Lunch with a view. The food (especially the burgers) are great, and the view of Charleston and the water is beautiful. They also have a patio outside overlooking the city if you like dining al fresco (too hot for us in July so we ate inside).

Note: I have not eaten at the following restaurants, but they came highly recommended for breakfast/brunch/lunch like the others which we all loved

The Park Café (Breakfast)
The Daily (Breakfast)
1 Broad Street (Breakfast)
Hall’s Chophouse (Brunch)
Callie’s Hot Little Biscuits (Breakfast)
Queen Street Grocery (Breakfast)
167 Raw (Lunch)
Butcher & Bee (Lunch)
Goat. Sheep. Cow (Lunch)
Home Team BBQ (Lunch)
Leon’s (Lunch)

Coffee Shop Suggestions:

The Daily
Saint Alban
Black Tap Coffee


Dinner Suggestions:

 The Ordinary * This is where we decided we had all died and gone to heaven. If you like seafood and more specifically oysters, then this restaurant is a MUST. We started with their “Triple Tower” (pictured above) which is a three-tiered seafood feast followed by various delicious seafood dishes. The atmosphere and drinks are also amazing. Total win!

Fig * This is a MUST if you’ve never been before. The atmosphere is a bit “blah,” but the food is AMAZING, and should always be on your list for dinner when in Charleston

Purlieu * This very small restaurant offers French-inspired dishes that are yummy and easy to share. They don’t offer cocktails, so be sure you’re in the mood for wine, which thankfully we always are. Note- this place isn’t in a bustling part of town, so you can’t walk around after like many of the other spots. Still worth checking out!

The Obstinate Daughter * I was told about this restaurant multiple times when I was researching where to eat in Charleston, but I didn’t eat there our first trip because it’s on Sullivan’s island, which I thought was “too far away.” However, it’s definitely not too far away even if you’re not staying on Sullivan’s Island, and well-worth the drive. It’s delicious for lunch or dinner, and I couldn’t get enough of their fabulous cocktails. Men and women of all ages will love this place, as it’s not too fancy, not too casual and the food is fantastic. Reservations are a must.

Note: I have not eaten at the following restaurants, but they came highly recommended for dinner like the others which we all loved- These are for more FORMAL dining options

Chez Nous
Hall’s Chop House
Butcher and Bee
Edmunds Oast

Note: I have not eaten at the following restaurants, but they came highly recommended for dinner like the others which we all loved- These are for more CASUAL dining options

Little Jacks Tavern
Pancito and Lefty
Home Team BBQ downtown location
Xiao Bao Biscuit
Taco Boy

Places to Grab a Drink/Appetizer:
The Belmont
Henrietta’s at The Dewberry Hotel

Goat. Sheep. Cow

Late Night/Cocktails:
Blind Tiger

The Warehouse
The Rooftop at Stars
Cocktail Club
Vintage Lounge
Uptown Social
Craft Wine Bar
The Griffon 


Where to Shop

This one is hard too, as there are SO many wonderful and unique shops in Charleston. However, we did quite a bit of “research” on this category while we were on our girls’ trip. Thankfully, we all share the same passion for shopping and eating, so most of our time there was spent doing both. We didn’t get a chance to do any real antiquing this time, but we hope to go back again and focus on shopping for home furnishings on our next visit. Most of the stores on my list are located on King Street so you can easily walk to everything. King Street is a very long street though, so be sure to wear comfy shoes if you plan to walk the whole street… or jump in a rickshaw like we did! Below is my list of our favorite shops for women/kids:


The Skinny Dip: Charleston Addition * We all LOVE this store, especially because it has a bar inside with FROZE!!! Who doesn’t want a glass of frozen rose when shopping?? This store carries items sourced from southern designers and they offer the cutest bags, shoes, clothes and gifts. We all left with a pair of Birdies slippers (pictured above), and we’ve decided to all buy at least one coordinating item from every city we visit together. I already want to buy three more pairs of these shoes! They are so comfortable and cute!

Hampden Clothing * Ladies upscale designer boutique with a beautiful selection of hard-to-find items by contemporary designers. We turned it into a fashion show, watching each other try on pieces we might not normally buy, and even though we didn’t all leave with something, it was fun browsing through all the goodies.


Pink Chicken Charleston * The cutest store with clothing and gifts/toys for kids and moms. I picked up the above pictured matching mother/daughter dresses (which you know I love), and G and I have already worn them and received a ton of compliments. I’ve loved this line for a long time, and I’ve shopped online, but never in one of their stores. It is a small space, but packed with the happiest toys and accessories, and I think all the moms left with something for themselves or their kids.

The Preservation Society of Charleston * A great gift store carrying locally-made goods like the Brackish Bowties (a Garden and Gun favorite), along with awesome coffee table books about Charleston and the South.

Beckett Boutique * Chic little boutique on King Street, with stylish clothes and cool jewelry. They were having a great sale while we were there, so of course we had an even better experience than normal and left with awesome white jeans and a Dodo Bar Or skirt for a steal.

Under the Almond Trees * A great baby and kids’ store with fun gear, toys, clothes and gifts, and we all left with unique bath toys, coloring books and thermoses for our kids.

Sugar Snap Pea * Darling kids’ clothing store- more trendy items than preppy/ traditionally southern

Ro Sham Beaux * This was really the only “interiors” store we visited on this trip. They offer the most amazing selection of lighting and furniture, but they also carry some clothing and accessories for women in their store. We left with some great earrings, handbags and a business card to call about ordering their new faux rattan outdoor furniture collection which we were all drooling over (not on their website as of now but will be soon).

SMALL, A Concept Store by Hampden * This is Stacy Smallwood’s newest store just a few steps away from her original store on King’s Street- Hampden. And though it is SMALL, it’s jam-packed with contemporary brands that are at a much lower price point than the lines she carries at Hampden. I loved just about everything in the store and wanted to buy all the dresses and earrings, and it took everything I had not to.


How to Get Around

For our group there was only one way to get around town: the RICHSHAWS (or Pedicabs- they are called both names, but are the same thing- a guy on a bike who pulls you on a cart behind him). We absolutely loved riding around in the rickshaws, whether we were heading off to shop or going out to dinner. Even when hot outside, you get a nice little breeze in the cart, and we always had the best time chatting with our “drivers”. I still don’t understand how they pull people around all day without passing out, but somehow they do, and we love them for it. We usually sat 2 ladies to a cart, but they could take 3 per cart as well. It’s a great way to see the city, though you miss an “official” tour guide. Our “drivers” always had the best stories to tell and we felt like we got the real “inside scoop” on a lot of information, like where the cast of “Southern Charm” lives and hangs out- ha! Below are the two companies we used the whole weekend, and I highly recommend either:

Charleston Rickshaw Co.


Charleston Pedicab


Ghost Tours

We weren’t really in the mood to visit any official museums while on our girls’ trip, but we did want to do at least one “activity” besides shopping while we were in the city. Charleston is famous for its “haunted houses” and seedy history, so we thought we’d try out a ghost tour. We originally signed up for a haunted ghost tour cruise (yes, on a boat), but it rained the night we were supposed to take the tour, so we had to make alternate plans. Thus, our second night in town, we signed up for the “Ghost City Tours of Charleston,” which is adults-only. Thinking that it would be extra-gruesome due to the “adults only” bit, we put on our walking shoes and met our guide by the Pineapple Fountain (need to see). Unfortunately, we were so underwhelmed by our particular tour guide that we snuck off from our group about 15 minutes into the tour and headed to a bar. I don’t want to discourage you from trying out a tour, as it was 100% a guide issue, and since the whole tour is basically storytelling as you walk around old buildings and churches, you need a good guide for this activity to be a success. I do think that the “Haunted Ghost Cruise of Charleston Harbor” would have been awesome, as it gets great reviews, so we will try that one again on our next trip!



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