Ever dream of a getaway that combines Southern charm, delicious food, and enough relaxation to recharge your batteries? Well, Charleston, South Carolina, might be your perfect escape! With it’s cobblestone streets, horse-drawn carriages around town, and delicious Southern cuisine (it’s a VERY foodie town, who knew?!), it’s super easy to fall in love with this city. I’ve heard it’s amazing any time of year, but the best time to visit Charleston, SC depends on what you’re looking for. More on that later ;)

Birthday Surprise: Taking My Hubby to Charleston for the First Time

This past February, I surprised my husband for his 40th birthday with a trip to Charleston – I literally told him we were going the night before we left with just a few hours to pack before our 5 AM wake-up call to make our flight (see the epic surprise reveal in action over on my instagram post here!) – and let me tell you, the whole trip was the BEST! Neither of us had been before, and it quickly became one of our favorite destinations.

The cobblestone streets are oh so charming!

Why Charleston Shines in the “Off-Season”

While most people would say that the city truly shines in spring and fall with comfortable temperatures, our February trip was absolutely wonderful. We experienced beautiful mild weather – perfect for exploring the city without getting too hot or bundled in layers. And it was a lot warmer than Chicago in February, I’ll tell you that!! Basically, I’m not sure there is a best time to visit Charleston, SC, but I’d definitely go back during their winter season. It did lightly rain on our last day but that didn’t stop us from ending our vacay on a high note!

Standing in front of the Charleston City Market

Charleston Has Something for Everyone

What’s more, Charleston caters to every kind of getaway, whether you’re craving a fun and romantic weekend with your significant other (hi, it me!!) or a fun-filled girls’ trip. In full transparency, I obviously did not know anything about the city (including the best time to visit Charleston, SC) so I hired a luxury travel consultant to help me plan the perfect experience for both my husband and I while we were there during their winter season. She was super helpful in many aspects of our long weekend, though a lot of our itinerary came from recs of our friends and family who had been to Charleston before. Let’s just say we did Charleston RIGHT.

Unlock the ultimate Charleston getaway with this amazing long weekend itinerary, revealing the best time to visit Charleston, SC, too!

Your Itinerary Awaits!

Here’s a sneak peek at your Charleston long-weekend itinerary, designed to unlock an unforgettable experience:

Day 1: Arrival day!


My advice is to arrive into Charleston EARLY because then you’ll have the whole day to explore! We chose to stay at the Dewberry Hotel and we LOVED it!! I would stay there again and again and recommend it to anyone. As soon as we stepped into the hotel, we knew we were in for a treat. The trendy and chic modern art-deco decor, impeccable service, and attention to detail made our stay truly exceptional. We couldn’t have chosen a better place to call home during our long weekend in Charleston.

Alternative hotels that I was considering were Hotel Bennett and The Spectator. They both are supposed to be amazing too! Hotel Bennett has a rooftop pool so I would consider staying there if we ever went back for pool weather :) The Spectator is where my brother and my sister-in-law stayed and they said it was awesome. Truthfully, there are so many great hotels as well as bed and breakfasts that you can’t go wrong!


  • Explore The Charleston City Market: Begin your Charleston journey with a leisurely stroll through The City Market. From local crafts to gourmet treats, this historic market is really unique and offers a warm welcome to the city!
  • Lunch: Indulge in some of Charleston’s renowned seafood at either 167 Raw Restaurant or The Darling Oyster. Whichever you choose, you’re in for a culinary treat! (We did 167 Raw, sat at the bar and it was THE BEST! There was a small wait for our seats so we shopped on King Street until we got the text that they were ready for us!)
  • King Street: After lunch, take a leisurely walk down King Street, known for its eclectic mix of shops, boutiques, and galleries. It’s the perfect place to enjoy some window shopping, pop into the cute Charleston-y boutiques, and do some damage to your bank account. But, worth it!!


  • Rooftop Drinks: Head to the Dewberry Hotel and unwind with refreshing drinks at their rooftop bar. With stunning views of the city, it’s the ideal spot to relax and soak in the Charleston ambiance.


  • Dinner at Husk: Conclude your day with a memorable dining experience at Husk. This restaurant was probably the #1 recommended restaurant to me while I was planning the trip! Known for its innovative Southern cuisine, Husk promises a culinary journey you won’t soon forget. We loved the food! When you make your reservations prior, ask to sit on the lower level. It’s a better ambiance than upstairs, trust!
  • An alternative plan would be to eat at Fig, a restaurant that people love (but we couldn’t get into) and do Sunday Brunch at Husk instead!
Unlock the ultimate Charleston getaway with this amazing long weekend itinerary, revealing the best time to visit Charleston, SC, too!

Day 2: Explore, Eat & Relax


  • Breakfast at Callie’s: Start your day with a quintessential Charleston experience – breakfast at Callie’s Hot Little Biscuit for their famous freshly made biscuits. Located in The City Market, it’s the most delicious way to fuel up for the day ahead!! PS They DO have gluten free biscuits and they were everythingggg!
  • Two Sisters Tour: Embark on a guided tour with the two sisters, which we heard was the best walking tour in Charleston. It definitely did not disappoint, offering insights into Charleston’s rich history and culture from the perspective of two sisters who have grown up there and who’s family has lived there for generations before them. From historic landmarks to hidden gems, this tour provides a fascinating glimpse into Charleston’s past and present! I highly recommend it!! Mary Helen led us and she was a real hoot! We learned so many fun facts about this charming city and saw things that we never would have paid attention to. We absolutely loved it.


  • Lunch at Lewis BBQ: Savor authentic Southern barbecue at Lewis BBQ. With mouthwatering meats and hearty sides, it’s a must-visit for any foody enthusiast. Note that you will have to take an Uber or taxi ride to get there because it is a little off the beaten path, but it’s not a long drive at all. There will also be a wait to order but it’s oh so worth it!
  • Couples Massage: Treat yourselves to a relaxing couples massage at the hotel spa. After a morning of exploration, it’s the perfect way to unwind and rejuvenate. TRUST.


  • Dinner at The Ordinary: Conclude your day with the most delicious meal at The Ordinary, which used to be an old bank. With it’s incredibly done inventive dishes, it’s the ideal spot for a fun and memorable evening in Charleston.
Unlock the ultimate Charleston getaway with this amazing long weekend itinerary, revealing the best time to visit Charleston, SC, too!

Day 3: Brunch and More


  • Sunday Brunch!! There are so many amazing class Charleston restaurants where you can enjoy a leisurely brunch experience. Some classics are Magnolias, Poogan’s Porch, The Palmetto Cafe, Halls Chophouse, and Slightly North of Broad (AKA S.N.O.B).
  • Optional Activities For the Day: If the weather permits, consider exploring Boone Hall Plantation & Gardens, where the movie The Notebook was filmed, or biking to Rainbow Row (many hotels have bikes for guests to ride if you want to do that!). Alternatively, spend your morning walking and shopping along King Street because you likely didn’t tackle the entire street yet – it’s goes on for miles!


  • Time to say your goodbyes! As your weekend in Charleston comes to a close, take a moment to reflect on the memories you’ve made and the experiences you’ve shared. Charleston may be saying goodbye for now, but its charm will stay with you long after you’ve departed. That is a promise!!
Unlock the ultimate Charleston getaway with this amazing long weekend itinerary, revealing the best time to visit Charleston, SC, too!

Other Fun Things to Do (That We Didn’t Have Time For):

  • Visit Fort Sumter National Monument
  • Explore the Gibbes Museum of Art
  • Take a carriage tour of historic downtown Charleston
  • Attend a performance at the Dock Street Theatre
  • Enjoy a sunset cruise along Charleston Harbor (this would be better planned for during the summer months!)
  • Discover the beauty of Middleton Place Gardens
  • Indulge in a culinary tour of Charleston’s best eateries
  • Experience the thrill of a ghost tour through Charleston’s haunted history – scaryyy!

Insider Tip: Charleston comes alive during festivals and events. Do a quick search to see if anything fun coincides with your visit!

The best time to visit Charleston, SC is…

There really is no best time to visit Charleston, SC!! While I loved our February escape, Charleston truly has something to offer year-round. If you’re craving sunshine, warm weather, and some beach days, summer is a great choice. Though, I know it can get pretty hot and humid during that time. Spring and fall offer comfortably warm temps and stunning scenery, making them the most popular tourist seasons.

If you end up booking the trip, whatever time of year it may be, you’re going to adore this city! Let me know if you use any of these ideas during your long weekend getaway! I can’t wait for you to experience the Charleston charm for yourself!!!!!


Then you must check out my epic guide to quick NYC adventures!! My husband and I have a special love affair with the city that never sleeps, and we try to go every few years for a quick mom-and-dad-only getaway. We are obsessed with the vibe, the energy, and the city hustle. I’m sharing all the NYC hot spots you must hit up to make the hours count! 


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