The Obsessive Compulsive’s Time-Saving Planning Guide to Charleston

My wife and I obsess about everything before we travel to a place for the first time. What is the best way to get there? How long does it really take? Are there traffic nightmares (i.e, Atlanta) along the way? Where should we stay? Is the hotel in a good location? What should we do? What do we wear? Most importantly, where should we eat?

Leah spent hours and hours reviewing hotels, restaurants, and tours ahead of our 4-day trip to Charleston in May 2014. She may have put more hours in researching the trip than we actually spent on the trip. I really didn’t do much of the research or planning, so I can say that the itinerary was awesome! She really did a great job.

We are probably not alone. Many of you have probably asked, or been asked, “where do you stay when you go to ___________ ?”

So, to those of you who are like us and fret a little over visiting a new destination, I offer this review of our first trip to Charleston. I hope that you can travel with confidence and know that you are experiencing some of the best that Charleston has to offer.

Getting There
If you live in the southeast, drive. There is an airport in Charleston, but you’ll probably have to fly through Atlanta, Charlotte, Baltimore, Chicago, or some major airline hub. In the time it takes you to drive to your airport, arriving 60-90 minutes ahead of your flight, fly to a hub, wait out your layover, fly to Charleston, get your bags, rent a car and drive to your hotel, you could have just driven from your home. The only exception is if you live in Nashville. Southwest Air offers at least one direct flight to Charleston each day. I might be tempted to fly if the flight was direct.

The drive, with the exception of a five mile stretch near Columbia, South Carolina, is all interstate. We left Birmingham at 11:00AM central time, picked up some friends near Atlanta, stopped on the other side of Atlanta for a late lunch, and we were in Charleston at 6:00PM central time (7:00PM local time), so a seven hour drive with a couple of stops. I’m a right lane, speed limit +/- 4mph driver. We weren’t in a hurry, but the drive seemed to fly by.

I researched taking Amtrak to Charleston. It can be done, but it costs about as much as a plane ticket and takes at least 4 times longer. From Birmingham, it’s a 10 hour train ride to Charlotte then, after a 5-hour layover, a 4.5 hour train ride to Wilson, NC.  Then you have another 3 hour layover before an almost 5 hour ride to Charleston. That’s about 28 hours of train travel, if the train is on schedule. That’s a big ‘if’, but that’s a story for another day.

So, if you’re in the southeast, drive. You’ll pay the hotel something less than airport prices ($11 to self park, $16 for valet) to park your car each night, but it’s the easiest (and still the most economical) way to get there.

Where to Stay
Deciding where to stay was, perhaps, the most stressful decision of the trip. We wanted to stay in a good location, convenient to everything, but far enough away from the happenings such that noise wasn’t a concern. If you’re planning a trip and have similar concerns, let me help you a little. All of Charleston is within walking distance, kind of like the French Quarter of New Orleans, but when it comes to late night noise, Charleston isn’t New Orleans.

We stayed at the Francis Marion Hotel at the corner of King and Calhoun. From a location standpoint, it was great. We were just a few blocks in any direction from great restaurants, shopping on King Street, and the College of Charleston (I like to see campuses, it’s a thing).

If you like a big, luxurious bathroom suite, the Francis Marion is not the place for you. It is a well-kept, but older, hotel and the bathrooms are small. You get a toilet, a single sink with very little counter space, and a tub with shower all conveniently placed in a space the size of a decent-sized closet. It was fine for me, but Leah had to put on her makeup at the table in the main part of the room.

The rest of the room was just a hotel room. Our view was south to the battery. Church steeples filled our view and we could see Fort Sumter in the distance. Other rooms, facing east, overlook Marion Square and offer a view of the Ravenel Bridge.

There are several B&Bs in Charleston. Friends stayed at Two Meeting Street Inn and loved it, but I’m way too much of an introvert to feel like I HAVE to sit at a table with strangers for breakfast each morning. I also like to get out and try different places.

From a location standpoint, anything within a couple of blocks north of King and Calhoun south to the battery is a good location. We walked the entire peninsula in a day, so don’t stress too much over the location of your hotel or B&B. They’re all within a stones throw of one another.

Getting Around
We parked our car when we arrived and didn’t see it again until it was time to leave.

As mentioned earlier, we walked the entire peninsula. Charleston is a very walkable city, at least the tourist area. In fact, if you’re looking for adventure, you can walk from Charleston to Mount Pleasant using the pedestrian lane on the Ravenel Bridge.

Remember that you are walking through one of the oldest cities in the country, complete with cobblestone streets and old stone, slate sidewalks. The shopping areas of King Street and East Bay Street have been improved but, especially when you get south of Broad Street, you will find some rough sidewalks. You probably don’t want to walk around in heels or push a stroller.

When we tired of walking, and we tired of walking, we used a Bike Taxi, an incredibly fun way to get around and see the city. It’s $5 per person for a 10 minute ride, and you can get just about everywhere in 10 minutes. The drivers were all recent college grads or college kids home (or in Charleston) for the summer. Friendly, polite, considerate…I don’t know enough kind words to describe the service.

We did, in retrospect, mess up and take a “taxi” (a bellman’s friend owned a Suburban) one time from the hotel to Hominy Grill. The three minute ride cost us $20. That seemed a bit steep and the driver was a bit too aggressive behind the wheel for my liking.

So, walk or bike taxi. There are several pedicab companies in Charleston, but we always used Bike Taxi. Ask for Danny and tell him “Roll Tide.”

What to Do
I’ll save “eat” for another section.

Charleston is a perfect ‘piddling’ town. Walk a while, grab a little bite to eat, walk a little bit, step in to a shop, walk a little more, take some pictures, walk a little bit, go on a house tour, then call the Bike Taxi because you’re tired of walking.

Charleston is a visual history lesson. You have to get out and about to see the history. If you’ve done research you know that there are several options to see the city. Probably the most recognizable is the horse and carriage tour, and there are several tour companines.

After a lot of research, we chose Palmetto Carriage for our tour. YouIMG_1983 will not find the place without asking someone around the market, “where is the big red barn?” It’s hidden in an alley that you absolutely will not see without a little help. It’s well worth the search, however, because our tour guide was magnificent. I wish that I could remember his name, but he’s the guy that married a girl from Wisconsin and watches the mini-series North & South at least once a year. I didn’t verify all of the facts that he shared with us on the tour, but he absolutely sold the story.
IMG_1986In order to alleviate traffic congestion ans keep tours moving, tour companies are assigned by lottery, at the start of each tour, one of three routes to take the group. We were assigned route #2 which took us down Church Street to South Battery and back up Meeting Street. Just sit back and enjoy the ride and the story. Don’t try to take pictures. Not a single picture that I took from the carriage was worth the space it took on the memory card, nor was it worth the sightseeing that I missed by trying to take the picture. Just enjoy the ride.

IMG_2056We selected, and I highly recommend, the Trot & Walk Combo Tour. After the carriage tour (the Trot), our guide took us on a 90-minute walking tour (the Walk) of the areas that we didn’t get to see on our carriage tour – the highlights of routes 1 and 3. Walking also offered us the opportunity, of course, to walk in some of the churches, cemeteries and graveyards that the guide pointed out on the carriage tour, and also allowed us to walk through some of the walkways and alleys that the carriage couldn’t go. I cannot recommend the Trot & Walk Combo Tour highly enough. It was great. Worth the trip to Charleston by itself, in my opinion.

There are also home tours scattered about the city (not part of the Palmetto Carriage tour). We visited two homes, the Calhoun Mansion and the Nathaniel Russell House.

The Calhoun Mansion
This is a magnificient home that was owned, of course, by one of the richest men in old Charleston. The exterior of the home and the gardens were something to see, but had they told me that the current owner (who lives there!) had filled the house with his own, eclectic collection of art from across the globe, I would not have forked over the $15-$20 to see the inside. I wanted to see a home as it sat in the 1800s, and this definitely was not it. There are a couple of pieces original to the home that you see – the Tiffany chandelier, for example – and the glass ceiling above the music room was impressive, but the gorrila and bison heads on the wall were definitely not ol’ man Calhoun’s. (

The Nathaniel Russell House 
This house was also owned by one of Charleston’s wealthiest families – not Calhoun rich, but the Russells were doing okay. This house was closer to its 1800s state than the Calhoun Mansion, which I really appreciated. After being a little disappointed by the Calhoun Mansion, we almost didn’t go on this tour. I’m glad that we did. The spiral staircase was a work of art and, for its time, incredible engineering. If you can only go on one home tour, I would recommend the Nathaniel Russell home, particularly if you want to imagine how the home looked 200 years ago. (

Two interesting things about the Russell House; 1. it was built right next to a graveyard (you wouldn’t do that today, but they thought nothing of it) and 2. our tour guide was Rudge Calhoun. Isn’t that funny? Talk about an old Charleston name. Rudge could not have been nicer or more accommodating. He spent an additional 10 minutes with us answer our specific questions after the tour officially ended. He still wouldn’t let us see the third floor, however, due to fire code (if a tour goes above the second floor, the home has to have sprinklers. The Russell House does not, and will not, have sprinklers).

Had we had another day or two in Charleston, I would visited the Aiken-Rhett House Museum and taken a ferry to Fort Sumter, and Leah wanted to visit the Boone Hall plantation. Guess we’ll just have to go back.

IMG_2108On our way – not really, because it was the opposite direction – but as we left, we took a drive over to Sullivan’s Island. We had lunch at Poe’s Tavern, but the real reason for the trip to Sullivan’s Island was to see the beach. The sand on Atlantic beaches just aren’t as bright as panhandle beaches, but I could see a group trip to Sullivan’s Island. I think it’s a great spot. Hang at the beach for day or two until you get sunburned, then ride in to town the next day for a shady tour. Talk about a variety of things to do, it’s perfect.

Charleston is a interesting little town. It’s the closest a town comes to running on island time that I can think of north of Key West. That impression could have something to do with us not having to catch a plane and, therefore, being able to take our time on the drive home. Still, it’s just a lazy (meaning, not in a hurry), comfortable little town.

Where to Eat
I guess you could go to Charleston and not eat any of the great restaurants, but why would you do that? Remember all that money that you saved a by driving instead of flying? Well, you’re going to want to let go of some of that cash and enjoy some really great food. It’s a culinary experience, really.

The Ordinary
IMG_1977We ate at The Ordinary after checking in to the hotel Sunday evening. I love a restaurant that is located in an old bank building. Lil’ Dizzy’s Cafe in the Whitney Bank on Poydress in New Orleans is now closed, but it was one of my favorites just for the experience of eating in a bank lobby and watching servers fill tea glasses at old teller windows. The ordinary offers that same kind of feel. We sat upstairs at a table that overlooked the lobby, a perfect spot to people watch and to imagine the comings and goings of Charlestonians making financial transactions 100 years ago.

I had the fish chowder and the East Coast Oysters, an assortment of six different oysters on the half shell. If I had to do it over, I might get a Shellfish Tower. I was the only one interested in the raw seafood, however, and the smallest tower was $65 and it was not small.

Dan had the Southern Fish Fry (the Sunday special). The fish was fried which, I suppose, makes it southern, but the serving was a little on the small side. I don’t know why, but I felt a little bad for Dan when the waiter placed the dish in front of Dan. It appeared to be one small fish filet, a single shrimp, and a lonely scallop trying to make it’s way to the shot glass of ketchup. In my memory, it was very sad looking. Dan said that it was great, but I’m not sure he tasted enough of it to really tell.

IMG_2066We ate at Magnolias for lunch after the Trot and Walk tour on the Monday of our trip. Hot and hungry do not begin to begin to explain how we felt. Magnolias lacked the atmosphere of The Ordinary, but most places will.

I started with the crab bisque (you’ll notice a pattern in my restaraunt habits). As I remember, it was a very creamy bisque. Some places will garnish the bisque with lump crab meat on the top, but this bisque was just decadently smooth.

I had been in Charleston 18 hours and had not eaten anything over grits, so I chose shellfish over grits as my lunch item. Billed as sautéed shrimp, sea scallops & lobster over creamy white grits with lobster butter sauce and fried spinach, it was a can’t miss. Except it kind of did.

Look, I’m the type of person that – if you tell me something is “the best thing you’ve ever tasted” – I expect the explosion of flavor to blow my ears off. Seemingly every restaurant in Charleston claims THE BEST “something” over grits. It’s usually shrimp & grits, but shellfish & grits should be stupid good.

The shellfish and grits wasn’t bad and, in retrospect, it was probably pretty good. It just didn’t live up to the build up that I may have unfairly placed upon it. All that I remember is the lobster being a little tough, as lobster is apt to be, and the butter sauce that was ladled on top of the dish.

I don’t recall what the wives had, but Dan had the fried chicken. It looked magnificent! He wouldn’t share. It was more of a southern portion than The Ordinary’s southern fish fry dish.

Fleet Landing
After the lunch at Magnolia’s and more walking, we opted for a more laid back dinner for Monday night. Housed in a 1940s retired naval building, Fleet Landing sits above the marsh of Charleston harbor and extends out in to the harbor, offering views of Fort Sumter and the Ravanel Bridge. From our outdoor table, we sat and watched the ships pass Fort Sumter and watched the lighthouse light spin. Just an easy, relaxing end to a day full of walking.

The menu was closer to traditional beach fare than Charleston fine dining. Think the Crab Trap to Cafe 30A. It’s the kind of place where you can put your elbows on the table, slouch down in your chair, and stretch your feet out in to the aisle and still feel good about yourself.

I started with (guess…) the She Crab Soup. The soup was very, very good. The soup was closer to Cafe 30A than it was the Crab Trap. One of the two best soup dishes that I had in Charleston.

Next came a half dozen oysters on the half shell, followed by a half pound of peel and eat shrimp. The oysters were good, the peel and eat shrimp were a little over cooked, but it was the perfect meal for just sitting and relaxing.

So that was our dining for Sunday and Monday. If I kept records of such, Tuesday May 13th may very well go down as the single greatest dining day of my life.

The feast began with an early lunch (before noon) at HUSK, which appears to be in an old house. It was very nice, but there was nothing overly fancy about the decorations. The tables were covered with brown craft paper. It was a very comfortable environment to sit and talk. It was the nicest place with craft paper tablecloths that I have ever been to, though.

IMG_2080The drink that I had before lunch was remarkable. It was called the Himalayd, or something to that effect. HUSK doesn’t have their non-alcoholic drink menu on their website, but this drink was light and refreshing and it had a cinnamon infused ice cube floating in it. Tasty.

You could make a meal off of the appetizers, which we did, but it didn’t stop us from ordering a main course. In addition to the complimentary basket of bread, we had a table full of skillet cornbread, grilled crostini with Tennessee cheddar pimento, pickled Green Tomato and Crispy Ham, and – my personal favorite – Kentuckyaki glazed crispy pig ear lettuce wraps, marinated cucumbers and red Onion, with benne seeds.

IMG_2083I know what you’re saying, “there’s no way that I’m eating a pig ear!” You got to get over that. The ear is thinly sliced so that is looks like slivers of bacon. It’s then flash fried and covered with Kentuckyaki (like teriyaki), placed in a small leaf of lettuce, and topped with cucumbers, onions and benne seeds. If the meal had ended right there, it would have been one of the best meals of my life.

If you prefer something more traditional, the cornbread was OUTSTANDING and the pimento cheese was exceptional also. Just when I thought that I had taken the single best bite of food in my life, I bit in to something else that was even better. I think you see where I’m going with this.

For my main course, I kind of messed up. I wanted the HUSK Cheeseburger with fried potato wedges, but I talked myself out of ordering it because it was a cheeseburger. Who goes in to a great place like this and orders a cheeseburger?

Smart people.
People who like exceptional cheeseburgers.
People who don’t overthink their order.
People who want to walk out of the restaurant saying, “THAT cheeseburger is the standard by which all future cheeseburgers will be judged!”

The patty is made up of ninety-five percent beef and 5% bacon. 5% BACON, KARLY! (At least, according to our tour guide.) Leah was nice enough to let me have a bite or two of her sandwich. As good as the North Carolina flat iron steak with jerky powder dusted Florida Potatoes, Ramps and Peppers, with South Carolina mushrooms and Kentucky worcestershire that I had was, the cheeseburger was better. Just outstanding.

If this may be your one and only time to eat at HUSK, order the cheeseburger. Yes, everything on the menu looks good – and I’m certain that it’s all good – but order the cheeseburger. Don’t overthink this. Don’t out-coach yourself. Order the cheeseburger.

Smarting a little from talking myself in to the flat iron steak, we walked around a little more. We walked through the market, up King Street, back down to the battery and actually did the Nathaniel Russell Home Museum tour on Tuesday afternoon.

Then came what I had been waiting for…

Hominy Grill
Hominy Grill is a little bit off the beaten path, but still within the service area of the bike taxi. Two $10 bike taxi rides beat one $20 Suburban taxi ride all day. It may be the closest to a ‘local’ place that we ate on the trip, except for the bagel place next to Jack’s Cafe. They have bagels, good bagels, but I didn’t think you’d want to read about a bagel. I digress.

Having skipped a cup of soup at lunch, I chose to start my dinner with a cup of She Crab Soup. I thought that the Fleet Landing soup was the best until I ate Hominy Grill’s soup. Had it not been crowded I would have licked the bowl. Instead I had to settle with scraping my spoon across the bowl, making the noise that darts through the air of even the most crowded diner and annoys some people to tears, until I had scooped up the very last drop possible. Absolutely stupendous.

Because it was our last meal in Charleston, and because it was the subject of a cease and desist letter from McAlister’s Deli, Leah and I decided to split a second appetizer – the Charleston Nasty Biscuit. It’s really not an appetizer, but it we didn’t care. It was our last night and our last meal in Charleston.

It was just okay. The chicken was good, the gravy was okay, but the biscuit was a little dry. Chick-Fil-A has me spoiled, I guess. It would be a better breakfast biscuit than it was lunch or dinner main course item. Alas, on to the main course.

Here’s what it takes to make good shrimp & grits; good shrimp, seasoned lightly and cooked until they are just barely done, piled atop a mound of grits, seasoned with just a bit of salt and cooked until it’s no longer soupy, but not yet dry. That’s really all that you need. As I do with most dishes, I’ll allow a sprinkling of crumbled bacon, and some garnishment of green onion. No gravy. No sauce. Ladies and gentlemen, I offer to you the best shrimp & grits in Charleston:


The kicker: CHEESE grits. I’ll allow it.

The shrimp were absolutely perfect. The grits would make every southerner proud, and there was no gravy in sight. You see, shimp are good. Grits are good. Bacon, well bacon is better than good. You don’t need gravy or butter or roumelade or hollandaise or whatever added to shrimp & grits. Whatever sauce you want to add simply takes away from the simple beauty of the dish.

I didn’t try all of them, but I saw alot of shimp/shellfish & grits plates in Charleston. My award for Charleston’s best shrimp & grits goes to Hominy Grill.

Dan had the Charleston Nasty Biscuit as his main course. I’m sure that Dan enjoyed every meal, but I feel he missed out a little on the Charleston dining experience.

So, ranking the restaurants in the order that I would visit them again:

2. Hominy Grill
3. The Ordinary/Magnolias/Fleet Landing

Poe’s Tavern (Sullivan’s Island)
Technically outside of Charleston, we wanted to visit Sullivan’s Island to see what it was like. While we were there – on the recommendation of a friend – we had lunch at Poe’s Tavern. It’s the kind of place where you can go and hide out from the heat of the day for a couple of hours. We weren’t hiding, but rather having lunch before we drove back to Birmingham, though. For beach fare, it was very good. I had the shrimp tacos with cole slaw. Very, very tasty. I had a friend tell me that he wouldn’t make the trip over to Sullivan’s Island just to go to Poe’s Tavern, and I agree with him. If you find yourself on that side of the bridge for some other reason, though, it’s a great option for a bite to eat or to just hide out.

Odds and Ends
When to go
IMG_2045We asked one of the friendly bike taxi ‘drivers’ when the busy tourist season was. He said that we were smack in the middle of it. According to him, April and May are the busy tourist months. I must say, I can’t imagine the city looking better than it did while we were there. The confederate jasmine is in bloom and you can smell it in the air everywhere. The window boxes and gardens are bursting with color, and the temperature is just a degree or two south of unbearable. You could tell, though, that summer heat and humidity were knocking on the doors of the city.

Shoes to wear
Shoes that are comfortable for walking. And pick your feet up when you walk on the old, uneven sidewalks. I reminded Leah of this about 100 times. About every other step she either tripped over a raise crack in the sidewalk or tried to twist her ankle stepping off a raised crack in the sidewalk. I’m sure Charleston has a hospital, but I really didn’t want to see it.

Running route
Start at the corner of King and Calhoun. Run toward the harbor (east?) until you get to East Bay. Turn right on East Bay and take it all the way to the Battery. At South Battery, take a right on King Street and run back to the corner of King and Calhoun. That’s 3 miles, give or take a detour to see a statue or to look out over the harbor. Go early. It gets hot about 8:00. Most of this route is in the shade but, as good southerners know, it’s not the heat that gets you, it’s the humidity.

Who to take
Charleston is a very friendly city. I didn’t see anything that would scare me away from taking the kids. You do, however, walk A LOT. I would not recommend, therefore, taking small children or older people. No way that my 8-year-old or 4-year-old would make it more than one day.

There you go. The obsessive compulsive’s guide to Charleston based on two obsessive compulsives’ first trip to Charleston.

You may have read this entire post and thought, “Charleston just doesn’t sound like a place that I’d like to visit.” I’m with you. I thought for a long time that I’d rather go to 30A, a place that I know and love, and skip this city that I wasn’t so sure about. I’m glad that Leah suggested the trip. What a fascinating city. If the idea of seeing where George Washington worshipped doesn’t interest you, and you don’t like history, or cool architecture, or old homes, or beautiful gardens, or friendly people telling great stories, or incredible food, then Charleston may not be the place for you. If you like one of those, though, you’ll love them all before you leave. My mind was completely changed during our trip, and I really can’t wait to go back.

If you’ve read this far and have questions or comments, leave them in the comment section or visit the contact page. I hope that you have a great trip to one of my new favorite cities!

3 thoughts on “The Obsessive Compulsive’s Time-Saving Planning Guide to Charleston”

  1. Please elaborate… “Because it was our last meal in Charleston, and because it was the subject of a cease and desist letter from McAlister’s Deli, Leah and I decided to split a second appetizer – the Charleston Nasty Biscuit.” (BACON!!!)

    1. McAlister’s took offense to Hominy Grill – and other restaurants – using the name “The Big Nasty” or “Big Nasty” for menu items. McAlister’s sent off cease a desist letters, which Hominy Grill reviewed and decided to change the name of their chicken and gravy biscuit. Thanks! Happy 4th!

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