Charleston is the perfect city for a quick getaway! The historic peninsula is small enough to walk end to end, SO much good stuff is stacked on about six streets, and if you’re not into planning? No problem – you can wander and let amazing food/drinks find you.
This was our second year ending a beach week here, and it has officially become non-negotiable. We spend a week in North Carolina with my partner’s family, which is lovely and loud and full of people, and then we peel off for two nights that are just us. He also used to live in Charleston, so we got to see friends of his while we were here, which is a nice bonus on top of the decompression.
Two nights is enough for a first visit, and it’s the right amount for a decompression stop. You get one arrival afternoon, one full day, and a slow morning before you go. We focused on food & drinks (per usual) this trip, but there is also a LOT of history in Charleston if that’s your jam.
Here you will find my saved map of everywhere we went and everywhere I researched, which you can add right to your own Google Maps to have all my recommendations at your fingertips. Below is our whole two-night itinerary. And at the end, I have listed all the restaurants and bars in case you would rather read it that way versus itinerary style.
New this time: I also rated and tagged everything on Beli, so if you just want the ranked short version, start there.
This trip is perfect for a group of gals, couples, anyone tacking a city onto a beach week, travelers who plan their days around food and drinks (hi, it’s me), and anyone who wants a walkable city where you don’t have to think very hard.
where to stay
We stayed at The Pinch and it is one of my favorite hotels I have stayed at in the US. It is a boutique property with around 25 rooms, which is small enough that after the first night every single staff member knew us. That intimacy is the whole appeal, and the place has a real personality, which is rarer than it should be. There are welcome cocktails, bikes out front for guests, a lovely lobby, and outdoor seating with a fireplace that I did not need in late August but very much noted for a future trip.
We were upgraded to a one-bedroom suite for free, so we had a full living room and kitchen plus a little breakfast nook we ended up using. But even just the bedroom would have been great! The bathroom is excellent, the shower is huge, and the robes are so comfortable I thought about them later. They also do turndown service, which I find so special when a hotel does: you come back from dinner and the bed is ready, the slippers are set out beside it, and it’s just adorable. I will now be requesting this from Skyline at home ;-).
Plus: The Pinch is part of The Edit, the hotel collection inside Chase Travel, so I booked it with my Chase Sapphire Reserve (affiliate link). That got us $250 off and I put the rest on points. It also got us early check-in (our room was ready at 2pm, which reshaped our whole first day), daily breakfast, the suite upgrade, a bottle of champagne, and a $100 property credit.
We spent the credit on drinks at Lowland, the bar downstairs, and put the leftover toward valet parking, which is not a glamorous use of a hotel credit but is an extremely practical one in a city where parking is the main hassle.
Breakfast is a DIY setup and I loved it: a waffle maker, quiches you can throw in the air fryer, pastries, bagels with every spread, and good coffee. It is cute to eat in the restaurant, but the first morning we carried it upstairs and ate in the suite’s breakfast nook, which felt like the actual luxury.
The catch, since every rec needs one: The Edit’s property list is limited and there is a 2-night minimum requirement, so it will not work for every trip. It worked perfectly for this one. Cannot recommend enough.
overall travel notes
getting there
Charleston International (CHS) sits about 12 miles from downtown, which is a 20 to 30 minute drive, so getting from the plane to your hotel is refreshingly painless. There are direct flights from a lot of US cities. We happened to already be in North Carolina for a family beach week, so we drove down.
getting around
The historic peninsula is extremely walkable, and that is the whole trick to Charleston. If you stay downtown you can walk to almost everything on this list. Our longest walk of the day was fifteen minutes and it only felt long because of the heat. The Pinch also has bikes for guests if you want to cover more ground.
Ubers/Lyfts are also very quick and relatively affordable.
when to go (hint: not when we did)
We went at the very end of August, which is not the smart month. It is hot and it is humid in a way that changes how much you can do between noon and four, and we also got rained on. We planned around it by putting the walking early and the drinks indoors, and it was fine. If you have flexibility, spring and fall are a better choice!
what to pack
Two things that follow from the heat: bring shoes you can walk miles in, and bring something for the sun, because there is very little shade on King Street in the afternoon. Otherwise Charleston is a casual, easy city to dress for.
our itinerary
day 1: Arrival + First Night
Check in at 2pm. Our room was ready early thanks to the Sapphire Reserve booking, which was a relief after a long travel day.
Late lunch at Bar 167. We were starving, so we walked over to 167 Raw, which everyone will tell you to do, and hit a two-hour wait. Worth knowing before you go: 167 Raw takes no reservations at all, first come first served. What saved us is that down a little alleyway they have a sister spot, Bar 167, which also has an oyster bar you can sit right at. We walked straight in on a Saturday afternoon while 167 Raw was packed. The menu leans Mediterranean, the oysters were great, and the crispy tuna rice we split was delicious. We loved it, AND it takes reservations.
A drink at Lowland, the bar at our hotel, which is where the property credit went. I had a blue cheese dirty martini that was probably my favorite martini of the year, and we split a smoked fish dip because dinner was late. If you are staying at The Pinch, do not overthink your first drink. It is downstairs.
Cocktails at Scotty Doesn’t Know. A speakeasy on East Bay, and absolutely worth the reservation. From the outside you would never guess, and then inside it looks like an old southern home. Their espresso martinis are the headline: I had a fairly straightforward one and Skyline had a tiramisu version he loved, which is the move if you like a dessert-leaning drink. Super fun.
Dinner at Chez Nous, which is a tiny French spot with a handwritten menu that they change every day. There are only about six things on it, which makes two people the perfect number: we each ordered something different from every section and split all of it. The homemade bread was my highlight and the steak was delicious. We sat outside on the terrace, which I would recommend if the weather allows. It was not that hot that night and it was really cute.
We did the wine pairing here too. It was good, though it did not land for me the way the one at Wild Common did the next night.
day 2: The Food and Drink Crawl
The whole day was built around one rule we set in advance: small plates and one drink per stop, save the appetite for the tasting menu. It is the single best structural decision we have made on a trip like this. (I had planned it as an oyster day and it turned into a general crawl, because we only ended up having oysters once. No regrets.)
Brunch at 82 Queen. Insanely good, and the interior is like a gorgeous indoor/outdoor home. Stunning space. The garden courtyard was closed because it was raining, which was a real loss, because it looked beautiful. We had the fried green tomatoes (a standout!), the barbecue shrimp and grits, the crab cake benedict, and a spicy bloody mary.
Shopping on King Street. Mostly window shopping, though Skyline bought a couple of things. It is also worth walking through the Market, which is right off King. We picked up souvenirs there last year.
Drinks at Citrus Club at The Dewberry. Eighth floor, panoramic views over the peninsula. Check in at the lobby desk to get an elevator pass. We sat inside at the bar because it was so hot, and I would honestly recommend that: the view is still amazing and the bar is where the good stuff happens. I had a gin drink I loved and they make a very good Hugo spritz.
Oysters at The Darling Oyster Bar on King Street, where we met up with Skyline’s friends. They run an oyster happy hour even on Sundays, which I appreciated, and it was $1.50 for one variety. So, so good. Cute space too. We were four so we took a table, but if you are only two, sit at the oyster bar.
One more drink at Pink Bellies on King Street. Chef Thai Phi’s Vietnamese spot, with an Asian-inspired cocktail list that is doing something really interesting. I had the Pho cocktail, which is inspired by the soup, somehow tastes like it, and is somehow also an amazing drink. The food looked great and I want to go back for a real meal.
Dinner at Wild Common. Far and away our favorite meal in Charleston. Just wow. The service, the food, and the wine were all incredible. It is a tasting menu with an optional wine pairing, and take the pairing: the sommelier was excellent and I could actually taste why each wine went with each dish, which is not something I normally say. We upgraded to the caviar course, essentially a caviar benedict, and it was next level and completely unique. We skipped the Wagyu upgrade and did not miss it. Plan on a couple of hours minimum. It is a splurge and I am so glad we took it.
day 3: A Slow Morning
Breakfast at the hotel, included, DIY, and unhurried. Then we lounged around the room for a while, which is the actual point of a decompression stop, and headed out.
If you have more time than we did, this is the morning for some history!
in conclusion
Charleston is walkable, food-driven, small in the best way, and completely doable in two nights. It is a great standalone long weekend, and it is an even better second half of a trip, which is how we have now done it twice. If you are already going to be somewhere in the Southeast, it is very much worth tacking on.
We will be back. There is an entire list below of places I researched and did not get to.
recommendation lists
everything mentioned above, organized by category for those who prefer it that way! you can find all of these, plus more places that i researched and had recommended to me, in my google map. everything is also ranked on my charleston list on beli.
restaurants
- Wild Common – Our favorite meal in Charleston and the anchor of the whole trip. Tasting menu, take the wine pairing, upgrade to the caviar and skip the Wagyu. A couple of hours minimum, so do not schedule anything after. Link here.
- Chez Nous – Tiny handwritten menu that changes daily, about six dishes total. Two people can order the entire menu and split it, which is exactly what you should do. Homemade bread and the steak. Sit on the terrace. Link here.
- 82 Queen – Insanely good brunch in a stunning indoor/outdoor space. Fried green tomatoes, barbecue shrimp and grits, crab cake benedict. Ask for the garden courtyard and hope it is not raining. Link here.
- Bar 167 – The sister to 167 Raw, down an alleyway just off lower King. Mediterranean-leaning, same East Coast seafood, its own oyster bar, and unlike 167 Raw it takes reservations. Get the crispy tuna rice. This is your move when 167 Raw is a two-hour wait, which it will be. Link here.
- The Darling Oyster Bar – King Street. Oyster happy hour runs even on Sundays, $1.50 for one variety. Sit at the oyster bar if you are only two. Link here.
- Pink Bellies – Vietnamese from chef Thai Phi on King Street. We only made it for drinks, but the food looked excellent and it is top of my list for next time. Link here.
bars
- Lowland – The bar at The Pinch. The blue cheese dirty martini was probably my favorite martini of the year, and the smoked fish dip is worth ordering. If you are staying there, this is where your property credit goes. Link here.
- Scotty Doesn’t Know – Speakeasy on East Bay, book on Resy, worth the reservation. Espresso martini, tiramisu martini, and a great Vesper. Looks like an old southern home inside, which you would never guess from the street. Link here.
- Pink Bellies – The Pho cocktail. It tastes like pho and it is delicious, which I did not think were compatible facts. Link here.
- Citrus Club at The Dewberry – Eighth floor views, get your elevator pass at the lobby desk. Sit inside at the bar if it is hot. Great gin drinks and a very good Hugo spritz. Link here.
researched and didn't get to
- 167 Raw – The one everyone sends you to, and for good reason. No reservations, first come first served, so either go early or go to Bar 167. Link here.
- The Ordinary – Widely called the best oysters in the city. Opens at 4pm on Sundays, needs its own night and a reservation. Top of my list for next time.
- Leon’s Oyster Shop – For chargrilled, which is the third preparation you want if you are doing an oyster tour of the city.
- Rappahannock Oyster Bar – They farm their own, so this is supposed to be the purest raw version in town.
These are just a smattering of the places we got to in two nights, which is not many at all. Would love to hear your Charleston favorites in the comments!
