Grab your favorite travel partner (or go solo), leave the kids at home, and set your out-of-office reply. Charleston, South Carolina is calling. Known as “The Holy City,” Charleston is no stranger to charm, but it’s the grown-up, elevated experiences that make it a must for couples, girlfriend getaways, or anyone craving a curated escape. With centuries-old streets, world-class cuisine, boutique hotels, and exclusive experiences, this four-day Charleston itinerary, carefully crafted with help from Explore Charleston, is your ticket to indulgence, Southern style!
DAY ONE
Check In: The Mills House
Begin your adventure at The Mills House, a pink-hued architectural gem with deep Charleston roots dating back 170 years. It has been lovingly renovated and reimagined to honor the rich history of the city while celebrating the modern spirit of Charleston. The hotel is within walking distance of nearly everything in the Historic District and blends Southern charm with modern-day comfort.
Afternoon Stroll: Charleston Icons
Grab your walking shoes and begin with a casual walk through the heart of the city: Joe Riley Waterfront Park and the iconic Pineapple Fountain, the rainbow-hued facades of Rainbow Row, and the oak-shaded promenade at The Battery and White Point Garden.
Dinner: Costa Coastal Kitchen & Bar
Where local seafood meets Italian. Whether you are an adventurous eater or not, there is something for everyone. Pair your grilled octopus or lobster tagliatelle with a crisp white wine on the breezy patio.
Late Evening: La Cave
Be transported to the South of France at this elevated sipping lounge. La Cave offers extensive lists of French wines, high-end whiskies, and cordials meant to be sipped and paired alongside a thoughtful menu of small plates.
DAY TWO
Morning: Biscuit-Making at Callie’s
Wait… hear us out. We know you are on vacation but this isn’t your typical cooking experience. This is a beloved culinary experience. Get your hands in some flour and have fun biscuit-making at Callie’s Hot Little Biscuit. Owner Carrie Morey wanted to share her mother's biscuit recipe nationally and this November marks their 20th anniversary so Carrie is clearly doing something right. During this hands-on private class, you’ll learn the art of crafting tender, buttery biscuits from scratch. Hint: There is a not-so-secret “secret ingredient” you wouldn’t traditionally find in a biscuit recipe, but … you’ll have to take a class to find out what it is.
Late Morning: Private Hat Bar Experience with Southern Ruetz
Next, channel your creativity and personal style with a private session at Southern Ruetz. Known for their bespoke events and luxury experiences, one of their standout offerings is a custom hat bar. You’ll design a one-of-a-kind wide-brim felt or straw hat, choosing from an array of ribbons, feathers, charms, branding, and custom burn designs. It’s part fashion, part artisan craft, and entirely unforgettable. Bonus: You get to wear your creation for the rest of the trip (and collect compliments everywhere you go).
Lunch:
Treat yourself to a memorable lunch. Option #1: Grab a table at Church & Union. When you walk in, you may think you are in a church. And technically, you are. The church-turned-restaurant is an unforgettable setting. If you are an avid reader, check out the ceiling. The entire text of Sun Tzu's Art of War is hand-painted on the ceiling of the main dining room. And if you look closely, there are hidden messages from the artist up there too.
Option #2: If you’re craving something lighter (or just need a sweet fix), stroll over to Carmella’s Dessert Bar for artisanal pastries, espresso, or a scoop of gelato. Heaven in a cup.
Afternoon Wine Stop:
Make your way to Wine & Company where boutique wines take center stage. Their curated choices are perfect for tasting. Pair it with a charcuterie plate and settle in for a while. The layout of the bar, tables, and couches makes it easy to find a new local friend and chat for a while.
Dinner: XO Brasserie
Conclude your day at XO Brasserie, contemporary Chinese cuisine with a focus on Cantonese and Sichuan flavors. Order a round of cocktails, share a few small plates, some house-made dumplings and toast to a day well spent, one filled with flavor, flair … and a fabulous new hat.
DAY THREE
Morning Departure: Check In at The Inn at Middleton Place
By now you are likely ready for a bit of quiet and a little more elbow room. Hop in the car because you are trading the bustle of downtown Charleston for the peaceful sounds of crickets, frogs and wildlife. You’ll know you're close when the trees and moss start arching over the roads. The Inn at Middleton Place is located just 25 minutes away. This award-winning hideaway features floor-to-ceiling windows, minimalist design, and complimentary access to the adjacent Middleton Place estate.
Explore: Middleton Place Gardens and House Museum
Spend your day exploring Middleton Place, a National Historic Landmark known for its 65 acres of America’s oldest landscaped gardens. Wander among centuries-old camellias and reflecting pools, visit the house museum, and reflect on the site’s complex history.
Lunch/Dinner: Middleton Place Restaurant
You can actually walk from the Inn to Middleton Place restaurant via a trail on the property. Just follow the trail signs. The 10-minute walk is stunning. You’ll see wildlife, cross bridges, and view scenery that cannot be beat. Bring your appetite as the portions are as generous as the people serving you. Lowcountry dishes like shrimp and grits are prepared with ingredients from the estate’s farm and gardens.
DAY FOUR
Morning: Magnolia Plantation & Gardens
Just a few miles from the Inn at Middleton Place, Magnolia Plantation is a fitting finale to your Lowcountry retreat. As one of the oldest public gardens in America, Magnolia is deeply rooted in the story of the South. Walk through informal gardens but also take time to engage with the site’s important history. Magnolia offers interpretive exhibits and guided tours. Known for its wild, romantic gardens and diverse wildlife, the plantation is best explored at a relaxed pace.
Late Morning Return: Charleston City Market
After checking out of the Inn, return downtown for a visit to the historic Charleston City Market. This open-air market features local artisans, sweetgrass basket weavers, and handmade goods. It is the perfect place for a meaningful souvenir.
Charleston knows how to do grown-up fun right. It's the kind of place where history meets happy hour, and where every street corner might surprise you with a new favorite restaurant, boutique, or story. So pack your bags, grab your travel buddy, and head south. Be sure to rent a car, pack your walking shoes and get ready for a good time. Charleston is ready when you are… and trust us, it knows how to show you a good time. CharlestonCVB.com