The Good Life
with a Southern Drawl

The Best Of Charleston

By Amy Bailey — March 14, 2019

17 years ago a boy and girl started dating. The boy lived near Charleston so their dates were filled with evening strolls down Market Street and The Battery, dinners at the South’s best restaurants, weekends with friends canoodling on rooftops, late night drives to Folly Beach, and pillow talks about their dreams and future. I was romanced and I cannot imagine a better city to be romanced in.

One of the first conversations with my future father in law over The Peninsula Grill’s coconut cake was about how fast life moves. I remember he said that you spend your younger years dreaming about who you will marry, kids, jobs, where you will live and then it starts happening and once it happens it just spirals. One day you will wake up and realize that you’re there, this life you dreamed about you’re living it.

The first time we said “I love you” was in Charleston, I remember a lump so large in my throat I felt like I couldn’t breathe, and when the words finally left my lips tears rolling down my face. It was as if those words were the most important words I had ever spoken, little did I realize how many life-changing important moments we would face in the next 17 years.

17 years ago I fell in love in Charleston. Maybe it was our attraction, maybe it was our conversations, maybe it was our comfortableness with each other, maybe it was how we made each other laugh, and maybe it was a little bit of that Charleston charm.

On a recent family trip, our daughter loved hearing these stories and walking the streets that younger versions of her mommy and daddy once walked. It is a different trip than it once was, but to be able to share it with our daughter is beyond special. Although it is a wonderful romantic trip, it is equally or even more so a great trip for families.

Upon on our return home I had many people tell me, “Oh I’ve never been to Charleston, but I have always wanted to go.”

“Go! Go now!” I want to exclaim. It is one of the most charming, most beautiful cities in the world. This Southern paradise boasts beautiful architecture, lush gardens, stimulating history, and some of the best meals you will ever have in your life. There’s a soul and energy that runs through the cobblestone streets that strolls along East Bay that swims through the marshes that chatters through the City Market and soars from every rooftop that is incomparable to any place you have ever traveled. Whether you are planning your first trip or your 20th, here is your guide to this Holy City.

Where to Stay

Inn at Middleton Place – It’s not every place you stay that you are walking around the grounds and out of the blue a flock a sheep run right by you, but that is just another day at the Inn at Middleton Place.

Located about 30 minutes from downtown Charleston, the buildings and layout of the Inn at Middleton Place are an architectural marvel created to blend into the natural environment that surrounds it. The ivy growing up the buildings symbolizes how here the land is suppose to be more important than the buildings.

With access to the gardens and grounds at historic Middleton Place, the inn is an idyllic and educational place to stay for the whole family. Middleton Place is a former rice plantation and showcases the oldest landscaped gardens in the Southeast. Tours tell the stories of both the enslaved and free.

Adults will enjoy strolls through the gardens turning each corner to find a secret nook or a breathtaking view of the Ashley River. Children will be enchanted with the stableyards of carriage horses, sheep, peacocks, chickens, cows, and more. Pottery, welding, and woodwork demonstrations are held throughout the day.

Trails throughout the inn and gardens allow guests to roam for leisure or exercise. Don’t be surprised if you see an alligator while on a walk, keep small pups close by;)!

Hammocks can be found all around the property that invite guests to take a nap or read. The inn’s pool overlooks the Ashley River and is a nice place to relax in the afternoon. Each room offers plantation shutters, contemporary bathrooms with field soaker tubs. Guests also enjoy complimentary breakfast each morning 7-10am. Middleton Place Restaurant is located on the historic grounds and is an excellent choice for dinner.

The Inn at Middleton Place also has an equestrian center offering trail and carriage rides for guests. Kayak rentals are also available.

Each morning and afternoon I took an hour walk by myself. I found a secret garden nook where I would sit, meditate, and pray. It felt so good to have that time to be still, it created such a deep gratitude within me for that time with my family in such a beautiful place, and it made the vacation all the more memorable.

One morning as I was wondering through the gardens I turned to head back to the inn. As I turned the corner I looked down the aisle beside the reflecting pool. Two swans were swimming in the pool and in the distance towards the fog covered lawn of Middleton Place covered were the horses from the stableyard grazing on the dewy grass. It was such a beautiful, surreal moment. I quickly called my husband and daughter to hurry and we all just stood watching them as the sun rose.

For me the beauty of the Inn at Middleton Place provided a peace and solitude I rarely feel. Having those moments wandering through the gardens enriched our vacation and enriched my soul. I am yearning for the next time I get to visit this fairytale like place.

Belmond Charleston Place– Looking for a hotel located downtown? Arguably the best place to stay in downtown Charleston and the best hotel in the Southeast. Here you are not just a guest, you are a VIP. From the moment you walk in the door, the attention is on you and your family and how to make your stay the best it can be.

Enjoy rooms that are blanketed in the best amenities. A bathroom that feels like a spa, plush bedding you can sink into, and robes and slippers for all guests to get cozy in.

Club Level is great for families. You are treated to several complimentary amenities, including a full breakfast of pastries, bagels with toppings, variety of fruit, quiche, bacon, biscuits, cereal, benne wafers, freshly squeezed fruit juices, coffee and tea. Enjoy breakfast in the club room or you can take it to your room as well.

During the afternoon traditional tea is served at Club Level with sandwiches and pastries. Happy hour begins at 5pm with heavy appetizers followed by dessert at 8pm. After her first tea time at Charleston Place our daughter was speaking in an English accent for the remainder of the trip.

You won’t be the only ones treated like VIPs, your furry friends will get the royal treatment too. Charleston Place is one of the only pet friendly hotels in this very pet friendly city. Many restaurants will welcome your four-legged friends and around every corner you will see pups on parade.

The rooftop pool is covered by a retractable glass ceiling and surrounded by a large sun deck. You can enjoy sunset poolside or at the rooftop bar which is also a local hotspot. Many rooms also offer beautiful views of sunrise and sunset.

Charleston Place also boasts an award winning spa, a fitness center with steam room, and the best shopping in the area. With it being located on King and so close to Market Street, you do not have to worry about driving because you are in easy walking distance to most points downtown. Whether you take a long stroll down East Bay to the The Battery or want to quickly pop out of the hotel to peruse the artisans at Market Street, convenience and luxury combine for an easy vacation experience.

The Cottages on Charleston Harbor – Another excellent option with all the splendors of home less than 10 minutes from downtown Charleston, The Cottages on Charleston Harbor. These beautiful, waterfront homes are decked out with luxe furnishings, including plush bedding, large screened in porches with hammocks, fully equipped kitchens, and washer and dryer.

For those that enjoy exploring but some nights just want to enjoy a little solitude and cook in your own place or for those traveling with friends or families, The Cottages on Charleston Harbor are a superb choice.

The pool and sundeck area is gorgeous and great place to relax and spend the day reading or make a splash with family. With the limited amount of cottages for rent, you will feel like you have the place all to yourself.

For the golf lover, Patriot’s Point offers one of Charleston’s only public golf courses. Guests of the cottages also have access to beach cruisers. You can explore Patriot’s Point or if you are feeling extra adventurous you can board the ferry to downtown Charleston, a quick ferry ride and you are in the heart of downtown.

Where to Eat

The Ordinary – From the seafood tower to fresh catches to local veggie dishes cooked just right, this restaurant is a must and just so very cool. Sitting upstairs you get a balcony view of oysters being shucked and seafood towers being built, it was entertainment for the whole family.

La Farfalle – A delightful al fresco dining experience that was just a couple of blocks from Charleston Place Hotel, La Farfalle provided a beautiful courtyard ambiance and mouthwatering handmade pasta dishes. Each dish we ordered was so simple,yet flavored to perfection. We ended the meal with the best gelato I’ve ever had – a Basil-Olive Oil gelato.

Poogan’s Porch
Poogan’s Porch named after the dog that claimed this porch his, Poogan’s motto is “We believe in conversations on porches, Sunday brunch, old Southern dogs, ghosts!, seersucker, biscuits, homemade and handmade, sweet tea, handwritten recipes, friends old and new, great stories, gracious hospitality and our Moms. Not necessarily in that order.” And there is a reason this restaurant is a favorite of celebrities, politicians, tourists and locals – the incredible fare offered daily.

Five Loaves – Healthy, sustainable and plenty of plant based options, Five Loaves is dedicated to serving fresh, local food and has quickly become not just a Charleston favorite but an all-time favorite.

Burwell’s Stone Fire Grill

This 21st-century steakhouse appeals to both locals and visitors. Burwell’s partners with humane ranches and local farms to offer more selections, small plates and a fresh fish program.

Ms. Rose’s Fine Food And Cocktails – This fun spot is located in West Ashley a short drive from Middleton Place. Boasting a great menu full of variety and craft made cocktails, we actually ended up there on homemade ramen night and it was fantastic!

Peninsula Grill
One of the best restaurants in the country, Peninsula Grill does not disappoint. From appetizer to the famous 7 layer coconut cake, this is an essential Charleston experience.

Amen Street Fish And Raw Bar – One of the South’s best oyster bars. Find regional bivalves as well as tasty ones from the East and West coast. A great spot to sit outside and people watch too.

The Glass Onion
Off the beaten path, this casual lunch spot is a local favorite, this restaurant makes for a casual lunch spot. You must try the fried green tomatoes, the tomatoes are actually pickled before they fry them.

Hank’s feels like you just stepped into a lively party, date unknown, by recreating the ambiance of a classic fish house with an old fashioned saloon-style bar. Hank’s serves up some of the best seafood you will ever dine on. Try capers blade oysters from the area, they are small and salty and oh-so good. The crabcakes melt in your mouth and are the best I have ever had.

Pavillion Bar
Modern sophisticated and fun and located in the heart of everything, enjoy the day or night on the rooftop of the Pavillion Bar with an incredible view of market street listening to the horse drawn carriages clickity clack down the cobblestones. Delicious bites like the tuna tower and a selection of sip worthy mojitos.

Caviar and Bananas
Fresh, mouth watering goodness served deli-style. From Lobster Cobb Salad to Duck Confit Sandwich, this is a great lunch spot that is delightful, healthy, and quick. Peruse their shelves for some unique kitchen accessories too.

Where to Shop

Kids on King
A mommy’s or grandmommy’s delight, Kids on King, is a small children’s boutique where you will find the most adorable children’s clothes. Carrying brands like Pink Chicken, Luli and Me, and Biscotti.

Alexandra French Antiques
It isn’t a trip to Charleston without a stop at one of their antique stores. Alexandra French Antiques has beautiful, hard to find pieces at good prices.

Billy Reid
A great store for both men and women by one of our favorite Southern designers located on King Street.

What To Do

Coastal Expeditions – Just a short drive away in Mount Pleasant, Coastal Expeditions offers kayaking, paddle boarding, and even overnight trips to uninhabited islands. Our kayaking trip was one of the most memorable because on leaving Shem Creek and returning we were surrounded by dolphins playing. They were right next to our kayaks and it was quite the experience.

Ghost City Tours – Think it’s hokey? Think again, a ghost tour in Charleston is quite the experience. The history and the tales will entertain and leave your hair standing on it. Well worth your time and money.

Market Street – Located in the heart of downtown, Market Street is a must. Watch women weave saw grass baskets, pick up some benne wafers to snack on, and find some beautiful locally made jewelry.

Charleston Culinary Tours – Whether you choose a farm to table tour or a chef’s kitchen tour, these experiences give you an insider’s look into Charleston’s rich culinary scene. You will learn so much and meet new people too. These tours are also a great way to see the city by foot and learn your way around downtown.

Charleston Charters – If fishing is your thing, Charleston is a great place to do it. Try Charleston Charters for a half day or full day charter. An inshore adventure could leave your family with a nice redfish, speckled trout, or flounder catch.

Best Times of Year to Visit

Charleston Wine and Food Festival
The creme de la creme of wine and food events, this festival is unparalled in taste and hospitality. Whether you have the opportunity to attend one of the many dinners, an oyster roast, private event, or a special seminar, the Charleston Wine and Food Festival is a bucket list event occuring in early March. Whether you are a devout foodie or just someone who loves to cook, you will marvel at the culinary talent at this festival and celebrate the flavors in each dish.

Spoleto Festival
An eclectic celebration of the arts and one of the coolest art festivals you will ever attend. Occuring in May/June which means beautiful South Carolina weather and a full display of flora and fauna.

Fall Tour of Homes and Gardens
Want to plan a fall trip, attend the Fall Tour of Homes and Gardens hosted by the Preservation Society of Charleston and peek at heirloom silver and meander through carefully cultivated boxwoods during these docent-led tours that invite guests into some of the area’s most historic and architecturally significant dwellings.