The Cool Kids Guide To A Weekend In Charleston

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Why Charleston?

 Always seeking new and inspiring destinations to explore, and with some considerable American Airlines air miles burning a hole in my figurative pocket, it was time for a city break.

In recent months, Stefan and I have taken note of the growing number of friends who’ve returned home in awe from a weekend trip to Charleston, South Carolina. After some initial research we quickly realised how much Charleston has to offer - think cobblestone streets, horse-drawn carriages, pastel antebellum houses, history, shopping and fantastic food!

The city also shares my 'thing' with pineapples....needless to say we were in and I knew just the dress to pack!


Fly In For Free*

 (*kinda, sorta, after fees so not quite but near enough, “free”).

With fairly manageable flights via Charlotte, we could avoid the pains of Miami International Airport – an invaluable bonus - and experience the charm of Charlotte’s airport (another destination now added to the wanderlust list, based on its airport alone!). With air miles and only a smallish fee to pay we booked in. 

The perfect long weekend getaway can’t be taken up with lengthy travel time. But living on a small island provides you with fairly limited direct flights options, made even worse in the low season of September. With this is mind, and wanting to make the most of the weekend, we opted for a Thursday (afternoon) to Monday (morning) long weekend. 

Flight options:

Departure - Thursday 2:29pm AA #822 Grand Cayman to Charleston // Charlotte American Eagle #5507 Charlotte to Charleston arriving at 9:40pm

Return - Monday 9:15am AA #2007 Charleston to Charlotte // Charlotte AA # 821 arriving back to Grand Cayman at 12:30pm.

photo by    Emilia Schobeiri

The Dreamiest Places to Stay

Putting my trust in the fantastic blogging community, I scoured the web for the best bloggers' reviews of where to eat, sleep and play whilst in Charleston. There are certainly some great guides out there (namely Paper & Stitch + The Every Girl) but for accommodation the options seemed to fall short.

Air BnB To The Rescue

The most appealing blogger-approved hotel options started at about US$300 a night and for us visiting Charleston for 4 nights it would totally break the budget. For one night, an indulgent hotel experience at The Dewberry at US$400 per night could be justified, but for a city break where you’re out and about exploring the sights, it really doesn’t make sense! There are more middle of the road options like The King Charles Inn and the Mills House Hotel that look attractive and stylish but for us it didn't feel worth that bit more money (rather save it for shopping!).

We stayed in this really quaint and comfortable AirBnB on Queen Street (the Southern end of downtown) at a much more reasonable $175 per night. If we were to visit again, I think I’d prefer to be up the more northern end of King Street (where all the cool kids hang) but this worked out as a great hub for our first trip over. [Note – we will be back!]

Where To Stay:

The King Charles Inn $$ // Family style "inn" in a good location. An option if you want breakfast and simple hotel options. 

The Mills House $$ // Good location and it's millennial pink (need I say more?!)

 Air BnB Queen Street $$ // The perfect space for two. Beautifully kitted out and a good central location. 

Zero George $$$ // Gorgeous historic hotel with oodles of Southern Charm - honeymoon worthy I'd say!

The Dewberry $$$ // A beautiful hotel with a charming retro feel. Really where the bloggers stay (next time for sure!)

Air BnB Off King Street  $$$ // Another AirBnB owned by the same landlord and one that looks even more stylish and in an even better location!

Photo by  Paper + Stitch

Eat Your Way Around Charleston

We generally made a point to ask those we met in Charleston (and wow you meet loads as they are some of the friendliest people going) what they would recommend we do whilst visiting the city. They all had the same answer – you need to eat and drink your way around Charleston! 

Well, you don't have to tell us twice.

Out went the idea of no drinking and in went the delicious cocktails and scrummy food. We enjoyed avo toast with a twist at the uber hip cafe, The Daily, we stumbled in and enjoyed an incredible steak and sides at the one of the best steakhouses in Charleston, the Oak Steakhouse and we scoffed down some 1 am deep fried chunky chips that were well remembered thanks to the ketchup-splattered white jeans found the next morning after finishing a long night at Mac's Place - a sports bar to rival some of the best! 

But to top all of that, we enjoyed quite possibly our most incredible seafood dinner to date at anything but...The Ordinary. We could only get at table at 5:30pm but we took it (a little early to start...hence the second drunk dinner at Mac's Place at 1am #nojudging) - early but perfect timing as we got the best service from our fantastically down-to-earth waiter, John.

The Ordinary is located on King Street (as is almost everything) in an old renovated bank with 30ft ceilings and period floor to ceiling windows! The refreshing Dirty + Rowdy white wine started the night off well alongside crispy homemade potato chips and the stunning two-tier seafood platter (12 of the freshest oysters less than 24 hrs from being harvested, and the freshest, lightest snapper ceviche, shrimp, clams and cocktail sauce). [Note early diners are winners with 50% off happy hour prices on oysters]. 

For our main we went with the dish of the day, also aptly known as The Ordinary (after old English taverns referred to the daily specials as "the ordinaries"), being the baked lobster. Think scallops, leeks, shrimp and cheesy goodness and lightly fried snapped and veg - all of it was delicious! 

For dessert, because we still had space thanks to the very "normal" portion sizes (in America, what?!), we had the chocolate budino to share (chocolate mousse, whipped cream, salted caramel and caramel pecans); it was divine! The service was absolutely seamless and they made you feel like family! Take a cardigan, its pretty chilly inside.

Eating at 5:30pm and suggesting a cardigan, wow I sound old!


Where To Eat And Drink

The Daily $ // Sip a strong coffee or green smoothie and try some trendy twists on avo toast as you people watch in this trendy cafe. 

The Obstinate Daughter $$ // Worth the 25 minute drive out to Sullivan's Island, great value and a fresh, healthy and yummy menu to enjoy after a stroll on the beach. Make sure you save space for the incredible gelato downstairs. 

The Ordinary $$$* This was by far the BEST meal we had in Charleston and arguably one of the best meals we’ve ever had. A bold statement, I know but check it out and you'll see why. 

Oak Steakhouse $$$* // A moment of sheer luck strolling past and saying "let's try this place" - sat at the bar and rated it 5*. Fantastic steaks and really delicious sides. 

FIG $$$ // We couldn't get a reservation here and should have tried eating at the bar as we heard lots of good things about it and it's the sister restaurant of The Ordinary.  "FIG" stands for Food Is Good, need I say more? 

Husk $$$* // We didn’t make it to Husk as we were slow on marking a reservation but we did make it to the Husk Bar (of course!) and apparently they do a mean burger for lunch! Cocktails were good and fantastic bar staff!

Mac’s Place $ // A taste of American sports bar and deep-fried goodness. This was particularly enjoyed at 1am - great atmosphere and super friendly staff and patrons (or maybe that was the drinks talking....?!)

Stars Rooftop  $$ (and Restaurant) // Sophisticated rooftop with nice cocktails and buzzing atmosphere - restaurant looked popular too!

Henrys $ // Bar turned nightclub with 4 levels of every type of music, live music and a rooftop - what more do you need?


Not Worth Your Money

I hate to be the one to criticize a business that’s working hard to please customers but equally it’s frustrating when bloggers just seem to continually recommend the same places because they’re "on trend". For me, if it isn't good value for money, it isn't on trend!

We visited the following places based on online recommendations and found them to be very overrated.  Of course, everyone has their own wants and needs so I thought I’d share why we didn't rate these experiences and you can judge for yourself whether they seem worth your hard-earned money.

The Macintosh

This place has a lot of hype, being amongst some of the coolest restaurants on the north end of King Street. You obviously have to book and the servers are, of course, very polite. The décor is attractive and we didn’t have any catastrophic mess ups or dramas. But put simply, the food was disappointing. It’s a daily set but limited menu, which in itself was quite uninspiring. Options were quite bizarre with overpowering flavourings and very small portions.


If you’re looking for a basic American diner, this is it. If you’re looking for anything else, you won’t find it here. We found this breakfast option not worth the time.

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Shop Til You Drop

Being islanders, we are spoilt in many ways - endless sunshine (although not this month!), white sandy beaches and endless umbrella laden-cocktails. However, a good selection of shopping is our downfall. 

Charleston has a great mix of shopping and King Street is the perfect scale with a great selection of high street and boutique shops for a long weekend visit. Think chains like Kate Spade, Sperry, Sephora, Apple, Urban Outfitters, Forever 21, H&M, as well as gorgeous boutiques. So like all good islanders, we shopped til we dropped!

I have to give a huge enormous shout out to these to die for boutiques -  Maris DeHart and Beckett  Boutique. Not least for their down to earth staff but of course their gorgeous garments. I love finding home-grown boutiques that stock interesting and unique pieces and really seem to value your spending - bravo ladies!  


Things To Do

Rainbow Row // So many gorgeous colourful buildings in Charleston and this street really has them all.  Finish it with a walk to the water a and a view of Ravenel Bridge and a little walk to Battery Park. (source Paper + Stitch)

Farmers Market on Marion Square // On Saturdays from April through November, you can visit the Farmers Market at Marion Square Park for a taste of all things local in Charleston. In the past, its been ranked one of the best farmers markets in the entire country, so needless to say, it’s worth the visit. There are a great variety of farmers, food vendors, and local artisans to choose from. If you’re visiting in December, you’ll be able to experience a holiday market (instead of the regular market). (source The Everygirl guide)

Sullivan's Island // Although we live on an island, it is always so nice to see the ocean in its many different colours and a trip to Sullivan’s Island certainly didn't disappoint. Think Hamptons inspired homes on wisteria style lanes and vast sandy plains. It is just how you expect a Southern coastal town to look and the homes were eyedroppingly gorgeous! 

This is also the perfect reason to have a delicious lunch at The Obstinate Daughter (see above) and sample some Charleston-famous olive oil ice cream at The Beardcat's Sweet Shop

Turns out the name "Handsome Properties" is taken...better luck next time, Stefan! 

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What Are You Waiting For?

We found to Charleston to be the perfect mix of culture, foodie travel and relaxation for a weekend break. The city really has everything you could wish for and more. The Southern charm didn't disappoint and we met some of the friendliest, most down-to-earth people in Charleston.

It's not often that we plan to go back to visit a place, with so many cities yet to explore, but Charleston really has such a special draw that we'll certainly be back soon!

I hope you've enjoyed this guide to Charleston. Please let me know if there's anything you think that needs to be added and do get in touch if you're planning your own trip there - I'd love to live it vicariously through you! 

What To Pack?

Backpack for your day trips exploring;

Sunscreen, sunglasses, shorts and sun hat - it is hot;

Comfy shoes – you’ll do a lot of walking;

 Sundresses and sandals for the evening, (heels very optional);

Cardigan or light sweater just in case;

Bug spray;

A good camera to capture all the gorgeous architecture;

  Vitamin C supplements or berocca to keep you going through all the eating and drinking!