Overnight Date Trip to Charleston: Where to Eat, Drink, Stay and More

charleston
Sightseeing at Rainbow Row.

One of the hardest parts, in my opinion, of being a parent is remembering to be a couple. More like finding and making the time to be a couple, really. It’s so easy to get caught up in the day-to-day with kids, keeping up the house, grocery shopping, cooking dinner, working, and kids’ activities that it’s easy to forget about the things that made these moments possible. The hugging, kissing, flirting, snuggling, and especially dates, seem to get lower on the priority list.

If you’re lucky enough to have family close by to be able to go on dates regularly, I envy you. My family is two hours away in Savannah and my husband’s is all the way in Chicago, so quick and easy “let’s drop the kids off at the grandparents’ and go on a date” nights are very far and few between. His parents recently came to town for two months and better believe we took full advantage of having them here. We went on a date night AND… wait for it… an overnight trip away together while they were here, too! It was our first night away together since our babymoon in October 2020, and a hot, uninterrupted dinner followed by an actual night’s sleep without a baby waking every three hours or being kicked in the stomach by our 5-year-old sounded pretty good.

If you’re looking for a getaway that’s actually away without being too far away, I can’t recommend Charleston, South Carolina, enough! It’s an easy four-hour drive up I-95 N, and there’s so much to do and see. Plus it’s a very walkable city, so you can pack a lot into a short trip which makes it even more worthwhile. You don’t even have to get back in your car if you stay within the downtown area (unless you want to, of course).

If we were going on an overnight Charleston date, or I were to plan your visit for you, here’s what I’d suggest (it’s basically what we did and it was great):

Day One

Pack up the night before. Wake up, give the kiddos a giant smooch and hug, and hit the road. Swing through a drive-thru for coffee and breakfast, and leave Jax around 8 or 9 a.m. to arrive in Charleston in time for lunch. Head straight to Blind Tiger for lunch and enjoy an app and entree to share in the courtyard.

After lunch, head to your hotel or Airbnb to check in, unload, and freshen up. The gap between lunch and dinner can be filled with a ghost or trolley tour, shopping on King Street, happy hour at one of the many local pubs or craft cocktail bars, walking around and sightseeing, or absolutely nothing, depending on your interests.

For dinner, the back patio at Poogan’s Porch (a Charleston staple) if delicious southern cuisine is your thing, or The Darling Oyster Bar if you prefer your dinner on the half shell. Can’t go wrong with either! After dinner, enjoy the walk and head a few blocks to either Gin Joint for a one-of-a-kind cocktail or a glass of bubbly at Camellias Champagne Lounge inside Hotel Bennett. Wrap up the evening with a delicious dessert (including dessert cocktails and boozy milkshakes) at Carmella’s Cafe and Dessert Bar.

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Day Two

The next morning, sleep in (obviously, because NO KIDS!), then grab a coffee from one of the many local coffee shops to sip on while you get ready or enjoy the sights. We are brunch people, so I’d suggest brunch cocktails and one of the best brunches ever at Miller’s All Day or Page’s Okra Grill.

You’re definitely going to want to walk off your meal (because it’s so good you’ll certainly eat more than you should), so head to Rainbow Row or the Pineapple Fountain to see some famous Charleston sights, then stroll through the Historic Charleston City Market for a few local treats to take home. If you need a snack before heading home, grab the pimento cheese app from John King Grill and Bar (trust me on this), before hitting the road.

Banana bread and an espresso martini at Miller’s All Day. And would 10/10 recommend their fried chicken biscuit.

Are you the kind of people who go away and do as little as possible so you can relax? Or do you try to squeeze as much in as possible? We are the latter… and I’m honestly not sure which is better.

If you need other recommendations, here are some of our favorites, along with a few others that were recommended to me.

Getting Some Sleep in Charleston

Back courtyard at Poogan’s Porch — so quaint and charming. Perfect for date night! Try their fried green tomatoes with fried bacon jam.

All the Eating & Drinking

For Coffee:

  • Tricera: The Saffron Latte is my favorite!
  • The Daily: Serving great coffee and breakfast.
  • Bitty and Beau’s Coffee: This popular coffee chain is run by those who have disabilities and is more than just coffee — it’s a wonderful experience you shouldn’t miss.

For Breakfast/Brunch/Lunch:

  • Miller’s All Day: We went for brunch and had the banana bread, biscuits and gravy, and Miller’s Plate and I would 100% recommend all.
  • Page’s Okra Grill: The epitome of southern breakfast. So good.
  • John King Grill and Bar: If nothing else, stop in for the pimento cheese app. It’s served with Texas toast and pickles, and it’s delish!
  • Blind Tiger: Great burgers, good drinks, and a nice courtyard.
  • Toast All Day: Known for serving Southern breakfast classics in a chill setting.

For Dinner:

  • The Darling Oyster Bar: This stylish, vintage-inspired spot serves creative seafood dishes, fry baskets, and raw oysters.
  • Poogan’s Porch: We love this spot for a date night, especially the backyard courtyard!
  • Butcher and Bee: This hip outpost offers a rotating menu of inventive, seasonal cuisine.
  • Church & Union: Enjoy delicious cuisine in this former church featuring dramatically gorgeous decor.
Boozy Tiramisu and Death By Chocolate Shakes at Carmella’s.

For Dessert:

  • Carmella’s Cafe and Dessert Bar: We had a boozy milkshake there (the tiramisu shake, YUM!), and took a couple of mini cakes home to share with the family. Everything was excellent.
  • Kaminsky’s Dessert Cafe: Enjoy delectable desserts made in-house in a cozy atmosphere.
  • The Honey Hive: This late-night dessert hot spot boasts a full bar.
  • The Belmont: They make their own pop-tarts and they’re SO good! Sit at the bar and enjoy one paired with a cocktail or espresso martini.
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For Drinks:

  • Carmella’s Champagne Bar: It’s beautiful! All pink and crystal chandeliers dripping from the ceiling.
  • The Gin Joint: Pick a handcrafted cocktail from their menu, or tell them what flavor you’re in the mood for, and they’ll create something special for you.
  • Bourbon ‘n’ Bubbles: There’s something for him and something for her!
  • Citrus Club: Indulge and imbibe in this award-winning dining destination.
  • Little Palm: Many folks love this cute poolside cafe and bar.
  • The Cocktail Club: Enjoy craft cocktails in this stylish speakeasy-style bar with a rooftop terrace.
Local photoshoot by the river with photographers Valerie and Ed.

Fun Couples’ Activities in Charleston

  • Shopping on King Street: Every shop you could imagine, local and chain, you will find on King Street.
  • Ghost or trolley tour: So much history in Charleston!
  • If you prefer water sports, take a kayak tour.
  • Sightseeing: A few staple landmarks are The Pineapple Fountain, Rainbow Row, Boone Plantation (where The Notebook was filmed), and the Angel Oak.
  • This is my favorite tip: Have a couples’ photoshoot with a local photographer! My husband and I did this a couple of years ago, and they’re some of my favorite pictures of us, plus great memories with a special backdrop. (We used Valerie and Ed and I can’t say enough about them!!!)

Whatever you do and wherever you go, enjoy yourself and your much-needed break, Mama. Splurge on that glass of good wine, order your favorite menu item and eat it in one sitting while it’s hot, and call down to the concierge for a late check-out so you can sleep in. Every couple deserves a break from reality and responsibilities every now and then, after all!

If you have other Charleston recommendations, share them here!

Blakeley Vinicky
Born and raised in Savannah, GA, Blakeley has been a Jacksonville resident for more than 14 years. She moved to Jax temporarily for an internship at The Jacksonville Landing (RIP), fell in love with the city and a boy (her now husband), and ended up sticking around. She is married to loud and crazy Chicago-native Jimmy Vinicky of nearly 10 years, and has two daughters, Daisy and Poppy. In addition to writing for Jacksonville Mom, she works full time in Public Relations, runs her own lifestyle blog This Blonde Life, and is a freelance makeup artist. She loves adventuring with her family, and you’ll rarely catch her sitting around home doing nothing. Her favorite local spots include Sipper’s and Breezy coffee houses, Wicked Barley Brewing, Cap’s on the Water, Ink Factory, happy hour at One Ocean’s Azurea, and soaking up rays at the beach.

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