When my friends asked what I wanted to do for my 40th birthday, I had one answer: Charleston. A long weekend, the best group of women I know, and a city that manages to be equal parts charming, energetic, and delicious. We chose to go during Valentine’s Day weekend, and it worked perfectly for a girls weekend.
If you’re dreaming of a girls’ trip that blends Southern hospitality with seriously good food, rooftop cocktails and rich history, this guide is for you. Whether you’re celebrating a birthday, planning a Galentine’s Day getaway, or simply need a long weekend with your people, Charleston in February is an underrated gem you need to know about.
Why February in Charleston is Actually Perfect
Most people don’t think of February as prime travel season. But Charleston in winter is a well-kept secret, and honestly, I think we experienced it at its absolute best.
Think light jacket or sweater during the day. Comfortable enough to stroll King Street without sweating and cool enough to enjoy an afternoon cocktail at a rooftop bar. At night a jacket or coat is comfortable and flat boots dress you up while keeping you comfortable for walking.
February also means you get to lean into the Galentine’s theme in the most fun and girly way.
Where to Stay in Charleston for a Girls’ Trip
For a group trip, renting a house is the way to go. We stayed in an adorable pink house within walking distance of some of our favorite spots. It was so nice having a common space to decompress, pregame, and play games together on the last night—which was one of the highlights of the whole trip.
Our Recommendation: Rent a House
Look for rentals in the Cannonborough-Elliotborough or Harleston Village neighborhoods. For a group of 6–10, splitting a house will likely come out cheaper than hotel rooms, too, and adds so much more to the experience. Our house was on Line Street and the location was great. Even a 20 minute walk to lunch one day felt super safe and doable in the gorgeous weather.
Hotel Alternatives:
If a house isn’t your vibe, Charleston has no shortage of stunning hotels to choose from. When looking for a place to stay, location matters so much, since the city is very pedestrian-friendly. Here are a few options depending on your budget and preferred experience, from high-end luxury to classic Southern hospitality.
The Splurge: Hotel Bennett or The Dewberry
On the higher end of the budget are Hotel Bennett and The Dewberry, ranging from $500-$900+ a night. You can’t beat the location of either of these, both overlooking Marion Square, right off King Street (The Bennett) and Meeting Street (The Dewberry). Both offer award-winning dining, historic architecture and rooftop bars.
The More Budget-Friendly: The Francis Marion Hotel
Not far away from those luxury options, is the Francis Marion Hotel which offers a more accessible price point without sacrificing the “prime” location. (Nightly rates range from $220-$450/night). A favorite for its 1920s elegance and a historic landmark named after Revolutionary War hero Francis Marion.
The Bed & Breakfast: The Nicholas
If a more private, bed and breakfast is the experience you’re looking for, check out The Nicholas. Located in the moss-draped Harleston Village two blocks off Lower King Street, it’s a reimagined 1798 house, with 9 rooms and a private plunge pool. With rates ranging from $290-$499 per night, it offers a more intimate, local touch and includes an “Epicurean Grab+Go” breakfast.
Our 3-Day Charleston Girls’ Trip Itinerary
Before I dive into the best restaurants, bars and nightlife in Charleston, here’s exactly how we spent our long weekend, straight from the itinerary that kept us on track. And having the time of our lives.
Day 1 – Thursday — Arrival & Party Vibes
6:00 AM –We were coming from Central Florida, so we loaded up the mini-van and drove up super early in the morning. It’s about a 6 hour drive so we wanted to get there in time for a late lunch.
3:00 PM – We arrived at our house, chose our rooms and unpacked a bit before heading out to our first stop of the day, Bay Street Biergarten. We walked there from our place, which wasn’t long, however it we thought we took a wrong turn at one point. Once we got there, though, the food, service and atmosphere was great.
6:00 PM – From there, we kept things casual and took a ride-share to Edmund’s Oast brewery for craft beers and good vibes. We kept it going into the night at a recommended local bar that was walking distance from our house called the Recovery Room. Now that was an unexpected good time. I love when a good “see where the night takes you” works out.
Day 2 – Friday — Cheers & Chills
10:00 AM – First thing was first, Trucker Hat Roulette! If you’ve seen this on Instagram you know. Everyone wore all black, grabbed a mystery trucker hat, and spent the day in them. It sounds ridiculous, but it was hilarious. Ten out of ten, would recommend creating your own ridiculous group tradition.
12:00 PM – We took a stroll down to Brown Dog Deli for lunch and it was exactly what we were craving. Amazing sandwiches, all too good sounding to choose. I went with a French Onion Grilled Cheese and it was divine.
3:00 PM – Afterwards, we explored King Street, found a few rooftop bars and explored until we were ready for a break.
6:30 PM – Dinner reservations at Church and Union.
9:00 PM – Then, walking distance from the restaurant was the meeting place for our Haunted Ghost Tour.
Day 3 – Saturday — Galentine’s Day
11:00 AM – Saturday was Valentine’s Day, and we dressed like it. We all got dolled up in our reds, pinks and whites and headed out to Iron Rose for brunch.
1:00 PM – Then, we strolled in the gorgeous weather to see Rainbow Row and the Pineapple Fountain. What’s great about Charleston with such a large group, is everyone was able to walk off and do what they wanted when there wasn’t something planned. I kept the itinerary light, for those who wanted to explore more historical sites, head home for some downtime, or bar hop.
7:00 PM – We all had a big drive home the next day, so we spent some quality time in our adorable house—face masks on, Thai food ordered, and hilarious card games played. And somehow, Dirty Dancing ended up coming on and we all watched (while some of us performed dance routines for the group). It was the perfect ending to a perfect trip.
The Best Restaurants in Charleston for a Girls’ Trip
Three days in Charleston is definitely not enough time to enjoy all the foods it has to offer, but we did a pretty good job while we were there. Here are all the restaurants we visited and a few others that are highly rated from our list.
This was my big birthday dinner location, and it absolutely lived up to the occasion. It’s a church turned restaurant and the vibe was on point. The food was absolutely amazing, one of the best dishes I’ve ever had. Featuring Modern-American cuisine and crafted cocktails it’s definitely special occasion worthy. Make sure to book in advance (and request the main dining room)—this one fills up fast.
Iron Rose was our go to for Brunch on Valentine’s Day. The ambiance was perfect for what we were looking for and the mimosas were flowing. They have a really pretty courtyard area as well that we took full advantage of for photos.
One of our unexpected favorites from the trip. If you’re willing to take a very short uber to this brewery, it’s worth it. The atmosphere is great, the beers were delicious and there’s a great menu if you need to grab a bite. And for those who aren’t beer fans, they have a full bar.
I took a bit of a risk adding this place to the agenda, as it’s off the beaten path, but I’m so glad I did. The vibe of this place was exactly what I was looking for as our first stop in Charleston after a long drive. Local feel, tons of outdoor seating, and craft beer. And the food—wow. We opted for a bunch of apps and they were incredible.
If you are a sandwich lover, like me, this is a must add to your itinerary. The menu had sandwiches like Apple Butter Jeans (a pressed panini with turkey, ham, bacon jam, apple butter, brie spread, and arugula) and Totes Ma G.O.A.T.S (Boar’s Head Cajun Turkey, hot honey whipped goat, fig preserves, caramelized onion aioli, fontina, roma tomatoes and arugula.) We had a very hard time deciding what to order, and yes multiple bites were shared across orders.
Basic Kitchen is a great option for those seeking a more health-conscious menu. They focus on using seasonal, local produce to create food that’s nourishing and delicious. We didn’t make it there this trip, but next time I am there it will be a go to for lunch.
Millers All Day was my second option for brunch with the girls. With a more casual atmosphere, it wasn’t the Vday vibe I was going for, but it has great reviews. They also don’t take reservations, so check the wait time and plan ahead with this one.
Charleston’s Rooftop Bars & Nightlife Scene
Ok the Charleston nightlife scene is exceptional. From sophisticated rooftops to dive bars, there’s something for everyone. Here are the all the places we went on our trip and they are all worth a visit.
Located in the heart of Downtown Charleston, off King and Calhoun St., the rooftop has a beautiful view of the bridge and Marion Square. On a sunny February afternoon, this spot makes for the perfect location to lounge on the rooftop with a delicious cocktail.
You know you’ve found a great dive bar when it doesn’t even have a website. On our first night, we were recommended this bar from a local after they learned where our house was located. Just a short 10 minute walk down the street, it quickly became one of our favorite spots. Pool tables, cheap drinks, a DJ playing all the hits, and late night trivia? I mean you can’t beat it. We could not have asked for a better first night to kick off the trip. (And we won second place in trivia!)
The Citrus Club is a seriously classy joint. Located on the 8th floor of The Dewberry, it’s the highest rooftop in Charleston. With gorgeous views of Marion Square and the Charleston Harbor, it earned a permanent spot in our hearts. Especially when we tried the Wölffer Estate Dry Rosé Cider. If you are not a cider person, this will convert you. Bright, dry, perfectly effervescent, and absolutely iconic for a Valentine’s weekend girls’ trip.
Tucked directly behind the YETI store on King Street, this little dive was a hidden gem. And we discovered it by asking the sales clerk at YETI what his favorite bar was. It’s the perfect counterpoint to the rooftop bars and a reminder that the best moments on a girls’ trip are often the spontaneous ones. I also have to shout out the YETI store for making it on our favorite bars list. The shopping experience was on point, with live music and a free whiskey tasting while you shop.
Henry’s on the Market was recommended to us by some locals as a great place for live entertainment. It’s a 4 story venue with a different band on each one. Be prepared to pay the rich $20 cover to get in, but it’s a place you can definitely stay at all night. The top floor was a legit concert venue and the entertainment was worth it.
Activities & Sightseeing in Charleston
Between the eating and drinking, Charleston has plenty to keep a group of women entertained, charmed, and slightly spooked.
King Street Shopping
King Street is the main street and an absolutely essential part of a Charleston visit. It’s hard to miss and it’s filled with a good mix of national retailers and locally-owned boutiques. Window shopping is a blast, but there are also so many fun bars and restaurants to tuck into as well.
Charleston is considered one of the most haunted cities in America, and the ghost tours take that reputation very seriously. It’s the perfect combination of informative history and wonderfully spooky storytelling. Highly recommend booking in advance, and the after dinner walk was perfectly timed.
Rainbow Row, The Battery & Pineapple Fountain
No Charleston trip is complete without the sightseeing classics. Rainbow Row—the iconic stretch of pastel-colored historic homes, The Battery offering gorgeous waterfront views and the Pineapple Fountain which makes for the best group photo of the whole trip.
Walking tip: Downtown Charleston is extremely walkable. If you’re staying near King Street, you can cover Rainbow Row, The Battery, Waterfront Park, and back to King Street all on foot in a few hours. Wear comfortable shoes, though, the cobblestones are gorgeous but unforgiving.
Even though we didn’t get to fit this in, a carriage tour is one of Charleston’s most iconic experiences. These horse-drawn rides take you through the historic district all while sharing stories about the city’s history and architecture. Tours typically last about an hour and no two rides are exactly the same. It’s definitely at the top of our “next time” list for a slower, more immersive way to see the city.
We didn’t make it here on this trip, but the City Market is one of Charleston’s most well-known spots. Stretching several blocks, it’s home to dozens of local vendors selling everything from handmade goods to art and classic Lowcountry souvenirs.
The Perfect Charleston Girls’ Trip for Valentine’s Weekend
Charleston has a way of making you feel like time slows down. The streets are beautiful, the food is extraordinary, the history is everywhere you look, and the people are genuinely warm. February, with its mild weather, quieter crowds, and Valentine’s energy, might actually be the best possible time to experience it.
Whether you’re celebrating a milestone birthday, planning a Galentine’s Day escape, or just overdue for a trip with your closest friends, Charleston will exceed every expectation. Start planning, book your house, make your reservations, and get yourself to King Street as soon as humanly possible.
I celebrated turning 40 in one of the most beautiful cities in America, surrounded by my favorite women in the world. That’s the kind of birthday that doesn’t need a bow on it—it’s already perfect.
For more girls trip adventures and some wanderlust inspiration for your next vacay, check out these travel guides:
Scottsdale’s Ultimate Foodie and Adventure Girls’ Getaway
Ultimate Girls Weekend Getaway In Austin — Guide to Planning Your Trip
Classy Girls Weekend in New Orleans
