North America, United States

A Weekend in Charleston


If you’re seeking a low-key weekend that’s filled with amazing food, southern charm and lazy seaside views, Charleston is just the ticket. We’ve found the perfect place to book your stay and encourage a laid-back itinerary that’s heavy on impromptu exploration and cozy bars and restaurants. 

Our challenge: Book a weekend getaway that’s easy to get to, but far enough away to feel fresh, that doesn’t require loads of pre-planning, and that includes a comfortable home base (because, well, I’m eight months pregnant).

With those parameters in mind, we narrowed our options to Charleston, Santa Fe, or Palm Springs. A little poll on Instagram helped us make our decision – Charleston it was! A perfect choice, given a good selection of daily direct flights from Detroit via Delta. And better yet since we’d never been together.

Strolling along King Street and through the city’s many lush alleys
Gorgeous – but creepy – graveyards abound


The first step was to find that cozy home base hotel that I had in mind. We wanted to avoid a rental car, so walkability was key. And a spa was a nice-to-have ;) After some research, we landed on The Dewberry Charleston, and guys, we loved it. Located beside downtown’s Marion Square, the hotel is just a quick walk to King Street, where you can turn right for a slew of restaurants and bars or turn left for some epic shopping.

Charleston’s mid-century Dewberry Hotel

At first glance, the mid-century hotel’s exterior isn’t much to look at, having made its home in a 60’s federal building. But step inside, and you’re instantly greeted with the dimly lit comfort of the Living Room, outfitted with an intimate, brass bar – prime for craft cocktails – and several soft seating pockets scattered throughout the room. If you time it right, there’s likely to be some live music softly playing from the corner, too.

Guest rooms are small but simply lovely. Our originally booked suite was under repair when we checked in, so we were reluctantly downgraded for the first night, and happily upgraded to a Charleston Flat room – with soaking tub! – for our remaining two nights. If you can afford the splurge, you won’t regret a stay in these uber spacious corner rooms, loaded with windows, a vast bath and sweet seating area.

The soaking tub in The Dewberry’s “Charleston Flat” guest room
A cocktail and a mocktail in the hotel’s Living Room
Sweet city views
The spacious “Charleston Flat” sitting room



After checking in and making ourselves at home (including an Old Fashioned, mocktail and charcuterie board in the Living Room), we headed out to make the most of our Friday evening. The one reservation that we had made in advance was to the highly acclaimed restaurant Husk and since our seating wasn’t until 10 p.m., we opted to get a lay of the land with an evening Haunted Carriage Tour of the city.

Haunted Charleston … at night
Historic cemeteries can be found all over the city
Another lush walkway

I’m a sucker for a good ghost story, but if I’m being honest, the carriage ride left a bit to be desired. No part of it was actually scary – which bummed me out – but our guide did do a nice job of introducing us to the main areas of Charleston and providing some high level history of the region. I don’t regret shelling out a few bucks for the entertainment, but not sure that I’d recommend it. (Maybe other tours, like their Historic Walking Tour, would have been a better fit for us!)

We arrived at Husk a bit early for our seating, and scoped out two seats in the small adjacent Husk Bar while we waited, noshing on an appetizer and sipping a couple of drinks. It was busy and packed, just the way you’d expect it. If the weather had been nicer, it would have been wonderful to grab seats on their patio!


We were among the last to be seated for dinner at Husk, but let me assure you, it was totally worth the late reservation. The place is all that it’s cracked up to be. While the atmosphere is fairly basic, the menu and service are as elevated as you’d expect. Trevor started with a raw oyster selection and I began with the cast iron cornbread. Since the menu changes daily, I won’t get into too much detail, but suffice to say that we stayed through dessert and were the last ones to leave. Definitely recommend; just be sure to pop online and make your reservation well in advance!


On Saturday, we began our day with a stroll down King Street’s shops, popping into Candlefish, Savannah Bee Company and the tiny but well-stocked Preservation of Charleston Gift and Book Shop while we waited for a table at Millers All Day.


Calories don’t count in Charleston; order the cinnamon roll

Serving up breakfast, lunch and brunch, Millers is a retro diner that I’d like to ensure you check out if you make it to town. THEY SERVE BISCUIT FLIGHTS. And alcohol. Need I say more? Oh, right, cinnamon rolls, too. Epic cinnamon rolls. If you roll up and find an hour-long wait, do yourself a favor and add your name to the list; you can easily burn time walking up and down the block while you wait.

The afternoon was naturally reserved for napping (pregnancy, duh) but this girl rallied for dinner out. We grabbed a drink and appetizer at Felix on King Street (warm vibes and a nice, long bar) and then headed to The Ordinary next door for dinner, which had come recommended by an Instagram friend. How can you not love an establishment that classifies itself as a “Southern seafood hall and oyster bar?” Plus, it’s housed in an old bank building with sky-high ceilings and gorgeous arched windows. I had to sit out on the oysters, but Trevor indulged once again and raved.


The Ordinary restaurant is housed in a historic bank building
Blurry photo, but a date night to remember … xo


It was finally time to find the spa at The Dewberry. After huffing around the city by foot for two days, I was ready. I had booked a prenatal massage for myself and Trevor would receive a deep-tissue massage.

For a Sunday, the spa was busy and bustling, it’s little waiting area full of folks lounging in chaises. But no mind. The treatments were both amazing and while there aren’t any spa amenities to speak of, that was fine by us. We headed back to our room to get ready for the day and then headed straight to the elevator to kick things off with a late breakfast at the in-hotel bistro, Henrietta’s. Even if you’re not staying at this hotel, it’s dining options are worth a stop (including the top-floor bar, Citrus Club, with its pretty city views). Live, acoustic music played near the bar and we enjoyed an unhurried meal in a leather booth.


Brunch is served at Henrietta’s inside The Dewberry hotel

From there, we strolled down Meeting Street toward the water. Taking in views of the city’s historic mansions (stunning!), walking past the fabled Rainbow Row – which sadly wasn’t nearly as vivid as I was hoping – and passing plenty of engagement photo shoots in The Battery seaside park.

The Battery park in an unusually quiet moment
Charleston’s Rainbow Row

Our concierge had suggested a stop by the historic Nathaniel Russel House museum, the early 1800s home to a  wealthy merchant and slave trader. Walking through the opulent mansion was an interesting and disturbing glimpse into the past (we paid for the iPod audio tour), a reminder of how very different life was 200 years ago.

Dinner that evening was at a place we’d passed the night before, its windows steamed given a large crowd in its small space – Malagón, Mercado y Tapería – not far from The Oridnary. An intimate tapas restaurant and Spanish wine bar, it was a simple meal that didn’t disappoint.

The spiral staircase at the Nathaniel Russel historic house
One of many Spanish tapas at Malagon


Our flight out didn’t leave until the late afternoon, so we took full advantage of the morning hours. Well, I slept in, but Trevor ventured to Fort Sumpter via the ferry, where he helped hoist the American flag on the morning tour.

Once he returned (well worth the trek, by the way, he says), we walked up to Callie’s Hot Little Biscuit, which everyone will tell you is a must visit when in town. True, it turns out! If you can time your meal between the rush of breakfast and lunch hours, you’ll miss the long line and have the tiny order-only restaurant to yourself. (The cinnamon biscuits are to DIE FOR. But really, go ahead and try them all.)

Don’t blink or you might miss it – Callie’s Hot Little Biscuit joint
A savory, cheesy biscuit bite :)

Next door, I found my favorite shop in the city, Grit and Grace Studio, up a flight of stairs and packed with painted oyster shells, delicate jewelry and small gifts. I grabbed a couple of holiday gifts – and something for myself, of course – before we grabbed smoothies at nearby Playa Bowl Charleston (delish!) and grabbed a cab to the airport.



Wait. I didn’t even mention the weather. Our travel took place in late November and while we assumed that any destination in the Carolinas would be warmer than Michigan, we guessed wrong. It was cold. Downright blustery with some light snow and freezing rain. Generally miserable and entirely unusual according to the locals. But even bundled up, the city was still magical.

I’ve heard that there’s no bad time to visit Charleston and having lived through it’s worst weather, I think I’d agree. If we’d had a more flexible schedule, I’d have loved to visit during December to see the city decked out for the holidays. Maybe next time?!

The one tip that I would recommend to future travelers is this: embrace the foodie scene and book your meal reservations early. The best spots fill up early so unless you don’t mind eating super late or crazy early, get a jump on this part. And be prepared … there are SO many amazing restaurants, you should try as many as possible!

Also, wear your walking shoes. The city is easily walkable and if you stay near King Steet, all the better. There is so much to do and see within the area, but you’ll squeeze in plenty of steps along the way. And while you’re at it, peek around corners! The city is full of eerie tucked-away graveyards, lush gardens and secret alleys. If a gate is open, we say sneak a peek :)

Lastly, do like we were forced to do and slow it down. Take a tip and match your pace to the laid-back southern style that exists. Take naps! Plan your days leisurely. Soak it up and allow yourself time to just roam on your own schedule. Charleston is the ideal destination for slow strolls, late mornings and long evenings. And last but not least, always, always order the biscuits.

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