Happy Monday! Last week, I had the absolute pleasure of spending a few days in Charleston with three generations of women in my family - my incredible mom, my sister Liz, and my daughter Emma. We were there to celebrate my mom’s birthday (a little early - she has a special birthday coming up in September), and the trip followed a beautiful bridal shower for my daughter Anna in Greenville, SC, hosted by her future mother-in-law. After the festivities, the four of us road-tripped to Charleston for some quality time together. Emma was the only one who had been before, so we were eager for recommendations - I asked my Instagram community and got such thoughtful responses (thank you!). We arrived Sunday evening and left Wednesday evening, and we planned the entire trip around things my mom would enjoy - culturally rich, walkable, elegant, and just the right pace for her energetic, curious spirit (though no, she wasn’t up for a bike tour!) Below is a recap of what we did, in case you’re planning a trip yourself.
Charleston Weather in Early June: What to Know
Warm and humid: Expect daytime highs in the mid-to-upper 80s°F (29–31°C), with humidity that gives your hair a life of its own.
Evenings are mild: Temperatures usually stay in the 70s°F after sunset, perfect for outdoor dinners or evening strolls.
Occasional showers: You might get a short, passing rainstorm in the afternoon - it’s a good idea to pack a compact umbrella or light rain jacket just in case.
Air conditioning is everywhere: Hotels, restaurants, and shops are well cooled, so bring a light sweater or wrap if you tend to get cold indoors.
Pack light, breathable clothes: Think linen, cotton, and comfy walking shoes - especially if you’re doing tours or hitting King Street.
Charleston Girls’ Trip Itinerary (June 9–11)
Sunday Evening
• Checked into The Dewberry Hotel - chic, mid-century design, centrally located, and full of Southern charm.
• Toasted the trip with snacks and cocktails on the Citrus Club rooftop - great views and a cool vibe.
Monday, June 9
• Enjoyed a (large) leisurely breakfast at the hotel (and skipped lunch afterward!)
• Drove out for a historic tour of Drayton Hall, one of the oldest preserved plantation homes in the country - moving and thought-provoking.
• Strolled the gardens at Middleton Place - peaceful and beautifully maintained, ideal for a slower-paced walk.
• Returned the rental car and Ubered back to town.
• Afternoon of shopping on King Street - antiques, books, and local boutiques galore.
• Dinner at Vern’s - cozy, refined, and one of our favorite meals of the trip.
Tuesday
• Breakfast at the hotel.
• Took an historic walking tour with Kay Abrams - smart, witty, and full of great historical perspective. She was outstanding. walkitcharleston@gmail.com
• Lunch at Basic Kitchen - fresh, vibrant, and health-minded, with something for everyone. The corn ribs are a must-try.
• Visited the Nathaniel Russell House - a stunning Federal-style home with a fascinating story.
• More shopping before my sister Liz flew home.
• Dinner at Chez Nous - charming, intimate, with a handwritten menu that changes daily. Only two appetizer options, two entrees and two desserts, so if you’re picky, this might not be the place for you, but we loved it!
Wednesday
• Started the day with breakfast at the hotel - though Emma also couldn’t resist a stop at Callie’s Hot Little Biscuit for a local favorite.
• Took a lovely morning walk along the waterfront, stopping at the iconic Pineapple Fountain for photos and sea breeze.
• Explored The Charleston City Market, home to many local artisans and food purveyors - I especially loved browsing Southern specialties like hot sauces, Carolina Gold rice, pecans, and grits.
• Visited the Old Slave Mart Museum - a sobering and deeply meaningful experience we all felt grateful to witness.
• Grabbed a quick (and amazing) lunch at 167 Raw - the ceviche was the best I’ve ever had. Truly!
• Stepped inside St. Mary of the Annunciation Catholic Church, the oldest Catholic church in the Carolinas, and admired (it was closed on Wednesdays) the Kahal Kadosh Beth Elohim Synagogue just across the street - one of the oldest in the U.S.
• Squeezed in a little more shopping before heading to the airport for our early evening flights home.
As much as we packed in, there were still so many spots we didn’t get to - Charleston is truly a history buff’s and food lover’s dream. We were supposed to have tea at the Hotel Bennett (image above), but we were too tired and full! I received dozens of amazing recommendations from friends, followers, and locals (thank you!), so I’m sharing the full list below in case you're planning a visit and want even more options to explore.
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