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Travel Guide: A Long Weekend in Charleston, SC
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Travel Guide: A Long Weekend in Charleston, SC

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By now it should be no secret that Charleston, SC holds a special place in my heart. For more than 13 years we have been traveling there as a family for summer vacations on Isle of Palms and as a couple for long weekends in the city.

That puts us at about just under 20 visits to the Holy City (called that because the number of church steeples dotting the Charleston skyline).

So while I may not be expert level on all things Charleston, I can say with confidence that anything from the following itinerary will make your long weekend visit to downtown Charleston something amazing.


Where to Stay

While there are a bunch of apartment rentals to choose from, we have always gone the hotel route. We never cook a thing while in Charleston because the food scene is so good. So to us there is absolutely no reason to have a kitchen that we won’t use.

We enjoy having a cup of coffee, an evening nightcap, access to a gym (as if we ever use it though), and other perks and amenities of a hotel stay.

Through the years we have settled on a few spots that are great places to stay for the hospitality and the location.

The Dewberry

This former federal building looks unassuming and a little blah from the outside. But step in and you feel like you are walking onto the set of Mad Men. The service is top notch and the rooms swanky and super clean.

Located right in the heart of the city on Marion Square, it is a perfect place to call home base and walk to nearly everything on your to see list. On Saturday's the Farmer's Market sets up in the park opposite The Dewberry making it a great place to stroll and check out the vendors, food trucks and vibe. 

The Dewberry is outfitted with a spa, rooftop bar (the tallest in the city), cocktail lounge and event space. They put an emphasis on the tiny touches with herbal tea and hot towels at check in, the most alluring candle scent permeating all public spaces of the hotel, hand-chiseled and logo stamped ice cubes for the Old Fashioned cocktails in the Living Room, gratis car service within a 9 mile radius of the hotel plus so many other perks that make this a delight of a place to rest and relax.

The Dewberry

A room at The Dewberry  

The Restoration

This spot is the epitome of urban charm and Southern hospitality. The rooms are large but cozy and come with all kinds of perks and pleasures to make your stay exquisite. 

The rooftop pool is the perfect place to cool off during a hot summer day or just to relax with a book between adventures and cocktail hour. The attached coffee house will fuel you for your day ahead and The Library will help you wind down with a good book or cocktail in the evening.

In room spa services are also a perk of The Restoration (though we have never indulged in this – yet).

Located on Wentworth, The Restoration is tucked closer into the middle of the shopping and where there is more hustle and bustle. But that doesn’t mean it will be loud or overwhelming.

Harbourview Inn

The Harbourview Inn was a spot that we initially stayed in early on in our adult only weekend trips to CHS. Since our last stay and based on the website, it looks like they upgraded and redesigned the rooms which was needed.

The Harbourview is, as the name suggests, on the harbor and near the iconic pineapple fountain. With views of the harbor, Fort Sumter (a tiny view), the Ravenal Bridge and park, it is very much in the thick of things. It gets a little more touristy around here and parking requires a stay in the attached garage. But it is still a great location to call home base as it is walking distance to the Battery, King Street shopping, Queen Street restaurants and where many tours ordinate from.

A complimentary breakfast (which I have always found robust and delicious), evening wine and cheese reception and cookies and milk near bedtime make the Harbourview a little gem. Plus, if you are persnickety about your mattress (ahem), you’ll be thrilled to know that they have Temperpedic mattresses throughout all rooms.


Where to Eat

For a long weekend in Charleston, plan on bringing stretchy pants to make room for all the incredible things you will eat and drink while there.

Leon’s Oyster Shop

For something more casual but always a solid choice, head to Leon’s Oyster Shop. You’ll need to take an Uber or Lyft there if staying at any of the aforementioned locations. The vibe is super chill, the food is delicious (focus on oysters and fried chicken), the drinks are cold (rose on tap anyone) and the service is always solid.


It might seem weird to settle on an Italian restaurant in a Southern town but I promise it will be one of the best meals you have ever had. The restaurant just got a new chef and amplified some of its already delicious dishes. The happy hour is a solid choice if you are doing the eat all day thing. It would be wrong to miss the rotating agnolotti pasta dish.

Chasing Sage

This charming little spot in the Cannonborough Elliottborough neighborhood is a must visit. The influences of the Pacific Northwest meets Southern food in the vegetable forward menu that rotates regularly. The service is like that of white tablecloth restaurants but without all the fuss. We’ve also dined here with kids and found it easy to find something for them to eat. Literally everything on the menu is divine. You can't go wrong. 

167 Raw

This spot on King always has an absurd wait list with no opportunity for reservations. During our last trip, we put our name in and were told 2 hours and 45 minutes, which was fine since we had a tour to go on. The call came earlier that our table was ready so we had to exit the tour early. Lesson learned: just go shopping while waiting for 167. 

They have a strong oyster menu plus a rotating list of dishes based on the fish they get in that day. Weirdly, despite the long wait list, the restaurant was not filled to the brim. In any event, if oysters by day are your thing and you have the patience, you won’t be disappointed by this spot.


167 Raw oyster menu

 167 Raw Oyster Menu and Fresh Fish Board

5 Church

The great place about 5 Church is that it is a restaurant inside a former church. Can you say charming? The food is consistently good and the service thoughtful. The drink list is solid as is the wine list. It’s a little loud inside because of the lack of acoustics but that wouldn’t be anything to keep me away. It is tucked in a touristy location so that is, for me, not a highlight. But the spot and the food is worth working around the crowd.


Where to Drink

Now, we are admittedly getting older and crankier in our old age of 40s. Charleston is a party town and during the school year, is a college town. So my recommendations for where to drink meet these qualifications:

  • Good drinks with a robust wine or liquor menu
  • Bustling enough to not feel like a retirement home but not too loud that you can’t hear someone and can only read lips
  • Clean bathrooms and thoughtful staff
  • Glassware only
  • Good snacks if you find yourself hungry yet again.


The Living Room at The Dewberry

A swanky spot to enjoy the most addictive caramel and cayenne popcorn and stellar cocktails like their famous Old Fashioned or French 75 or Aviation. It is definitely on the chill end of the where to drink list here. But wow are the drinks perfection. Start the night there for a cocktail or simmer before heading to bed. 

 The Living Room at The Dewberry

A French 75 and Old Fashioned in The Living Room at The Dewberry 

The Cocktail Club

It can definitely be a little much with the kids and the crowds. But the drinks are incredible and the space is uber cool so it is well worth it to me. Plus – and my favorite – they have live music Thursday – Sunday with always, always, always good talent. If you go and are in the mood for a strong cocktail, try the Double Standard.

Vintage Lounge

This spot is super swanky and cool – as long as you are inside. Most recently we were sat  outside with the kids and we felt super out of place (and could not hear each other). They have live music on some nights and a fantastic wine list. We snubbed our nose at reservations and it was our mistake. Don’t make it yours too.

The Belmont

An adorable and tiny little place with great drinks and a super charming feeling. I couldn’t make a night of drinking here but it is worth a stop on King as you bar hop, particularly at the end of the night so you can indulge in a house made pop tart.


Another swanky and adorable spot with cool drinks, Southern-focused menu and live music is Prohibition. They don’t take reservations so you’ll have to get there at the right time or have some luck on your side. It’s worth taking a shot though.


Oh the happy hour at Husk is among our favorites. If we are in the area and it fits our time schedule with dinner reservations, we will often pop in here for a drink and a good snack.

The Gin Joint

I mean… if you love gin this is your honey hole. It is a tiny space so you either have the luck to catch a spot or you have a wait on your hands. But it is worth taking a whirl for the atmosphere and the drink list you won’t find anywhere else.


What to Do

I don’t like to be by tourists in the evening, I am a proud tourist during the day. There is SO much rich history in Charleston, you would be silly to not take part in a walking tour, trip to Fort Sumpter, take a class or go on a ghost tour (which would be at night with tourists).

We have done the horse drawn carriage ride on our first trip and I hated it. The history and the tour was great. But being sandwiched with a bunch of people on a cart pulled by a horse in the middle of summer (and while pregnant) was not fun. Plus there are too many stories of horses going lame because of heat exhaustion that I just can’t get behind or recommend this angle at seeing the city.

Instead tours are available by foot, scooter, air conditioned van or semi private carriage rides if you must (a better choice for horses).

We have done a few different tour companies and found them all to be pretty good - not one exceptionally better than the other. So my advice: Google your way through whatever tour sounds fun and feel confident that the people giving it are good stuff. 

We have found some really cool tours, wine tastings and new takes on touristy things through the Preservation Society of Charleston. A bonus is that supporting the programs of the Society means that the focus can continue to remain on the history of the city. 


Cocktail Mixing Class

We most recently took a cocktail mixing class at Circa 1886. It was a private event and we got to each make a drink based on our favorite spirit (gin for me, bourbon for the hubs). We also learned about making limoncello (and other derivatives of it) as well as sampled some various spirits we have never tried before. We learned things we never knew, got to learn more about the city from a unique point of view and spent some time together.

Wine Blending Class

A few years ago we took a wine blending class at the Grand Bohemian Hotel and wow was it fun. We learned about the varietals that go into making a wine, did some chemistry work and then walked away with two bottles to have later. It was a fun and interesting experience that took a few hours. If this is not something you can do at home, I highly recommend trying it while away.

Candle Making Class

If headed to CHS with the ladies and wanting to do a chill and non-touristy activity, book a class at Candlefish. You’ll learn about how to make a candle that burns correctly, go on an olfactory exploration and pour your own two, 9-oz candles to bring home. And because it is Charleston, you know there is cocktails. BYOB to get lit as they say.


Admittedly, there is a lot of drinking in Charleston. But even those who imbibe need to tone it down.

So between cocktails, you will find some great shopping opportunities in apparel, antiques, art, specialty food and more. King Street is typically where a lot of the shopping is, though there are some great shops by the harbor. Don’t miss the sandwich signs for spots located above street level.

Favorite places to dip into include the Anthropologie on King (I swear they have the best selection of all the Anthros), Candlefish, Copper Penny, Maris Dehart, Indigo, Sapphire Boutique and M. Dumas and Sons for the guys and Blue Bicycle Books for a local bookstore with lots of signed editions.


Charleston, SC is one of the most charming cities to visit for a weekend, a week, with a crowd or with your special someone. Once you go, you will want to return again and again. And with this list of things to do in Charleston for a long weekend, you’ll need a few visits to do and see it all.