The Perfect Girls’ Weekend in Charleston: A Local’s Itinerary

A downtown Charleston girls’ weekend is even more fun when everyone can stay together. Instead of splitting up among hotel rooms, you can have a house with a kitchen, a living room, and a backyard where the whole group can gather.

The Isla Suite is our first-floor suite in Charleston’s Cannonborough-Elliotborough neighborhood. It has four bedrooms, two bathrooms, and room for up to eight guests, along with a porch and shared courtyard. It is also a short walk from Spring Street, Cannon Street, and King Street.

Need more room? The Poppy Suite is directly upstairs in the same house. It has three bedrooms, two balconies, and parking for two cars, so you can keep a larger group together while still giving everyone space to spread out.

We are Brandy and Chad, and we personally host The Charleston Suites. When you book directly with us, you receive our best available rate and communicate with us instead of a call center.

Once you have your house, use this itinerary to eat, drink, shop, and explore your way through Charleston with your favorite women.

Friday: Settle In and Start Celebrating

Whether you drive or fly into Charleston, there is a good chance you will arrive a little too early for check-in.

Option One: Lunch and a Walk

Begin with lunch at Park & Grove. This neighborhood restaurant creates seasonal dishes inspired by the farms, fields, and waters surrounding Charleston. It is relaxed, delicious, and a great place to toast the official start of the weekend.

After lunch, take a walk around Hampton Park. The 60-acre park is filled with walking paths, a fountain, grand magnolia trees, and beautiful seasonal flowers. It is the perfect place to stretch your legs and catch up after a morning of traveling.

Option Two: Seafood and King Street Shopping

If your group is ready to jump right into downtown Charleston, head to 167 Raw Oyster Bar for lunch. This lively King Street favorite serves fresh oysters, ceviche, lobster rolls, tacos, and frozen cocktails. It does not accept reservations, so put your name on the list first and use any wait time to begin shopping on King Street.

After lunch, continue exploring the stores and boutiques along King Street until it is time to check in. Just remember that anything you buy on Friday has to fit in your suitcase on Monday!

Once it is time to check in, head to The Isla Suite, unpack, claim your bedrooms, and get ready for your first night out. From our downtown Charleston vacation rentals, you can walk or take a quick rideshare to most of the places on this itinerary.

Start the evening with rooftop drinks at The Watch. Located on top of The Restoration Hotel, The Watch has plenty of indoor and outdoor seating, along with sweeping views of Charleston’s rooftops and steeples.

For dinner, choose between Allora and V Modern Italian. Allora is a colorful coastal Italian restaurant on Spring Street with handmade pasta, crudo, spritzes, a rooftop lounge, and even a streetside gelato window. It was practically made for a girls’ weekend.

V Modern Italian is another great choice if your group wants dinner to lead right into a night out. It serves fresh pasta, pizza, cocktails, and contemporary Italian dishes in a lively, music-forward atmosphere.

Saturday: Explore Downtown Charleston

Saturday is the day to really explore downtown Charleston. Wear comfortable shoes because you will be doing plenty of walking, shopping, sightseeing, eating, and drinking.

Start with coffee at Babas on Cannon. This European-inspired neighborhood café is the perfect place to grab a latte and something small to eat before walking toward Marion Square.

If you are visiting during market season, stop at the Charleston Farmers Market. It is held in Marion Square on Saturday mornings from April through November, with additional holiday markets in December. You will find local produce, prepared food, flowers, art, and plenty of Charleston-made gifts. If the market is not running during your visit, simply begin the morning with shopping and sightseeing.

Spend the rest of the morning visiting some of Charleston’s most recognizable landmarks. Walk through the narrow streets south of Broad, admire Rainbow Row, and visit Waterfront Park to see the Pineapple Fountain. Continue toward The Battery and White Point Garden for beautiful harbor views and rows of historic homes.

If your group wants to get out on the water without committing to a full boat tour, hop aboard the Charleston Water Taxi. It is an easy and affordable way to see the city from Charleston Harbor.

When everyone is ready to sit down, stop for lunch at Frannie & The Fox. Located inside Hotel Emeline, its charming courtyard is the cutest place to relax and catch your breath after a busy morning.

Next, have an afternoon cocktail at Little Palm. With colorful drinks and a playful poolside atmosphere, Little Palm brings a little bit of South Beach energy to Charleston.

Before dinner, share something sweet at Carmella’s Café and Dessert Bar. Dinner may be late tonight, so this is the perfect opportunity to have dessert first.

If your group has its heart set on Chubby Fish, send one person to get in line before it opens. Chubby Fish does not accept reservations and opens at 5:00 p.m. Tuesday through Saturday. The line can form well before opening, so arriving early is important.

Once your name is on the list, have a pre-dinner drink and a few Spanish small plates at Estadio. This intimate restaurant is known for gin and tonics, tapas, pintxos, vermouth, sherry, and natural wine.

You can also head directly next door to Seahorse, the cocktail bar and supper club created by the team behind Chubby Fish. Seahorse serves seasonal cocktails, excellent wine, and a small, frequently changing menu that highlights local seafood. It does not accept reservations, but you could not ask for a more convenient place to have a drink while waiting for your table.

End the night with dinner at Chubby Fish. The menu changes daily depending on what local fishermen and farmers bring in, and the incredibly fresh Lowcountry seafood is worth the extra effort required to get a table.

Sunday: Visit the Old Village and Sullivan’s Island

On Sunday, cross the Ravenel Bridge and spend the day exploring Mount Pleasant’s Old Village and Sullivan’s Island. This part of the weekend has a slower pace, beautiful scenery, and some of my favorite restaurants in the Charleston area. You will still be based downtown, so the drive from The Charleston Suites is an easy trip over the bridge.

Begin with brunch at Post House. This beautifully designed neighborhood inn and restaurant has become one of the Old Village’s most recognizable spots. Make a reservation in advance because its brunch tables fill quickly.

After brunch, walk through the Old Village and continue to Pitt Street Bridge. Along the way, you can admire the quintessential Southern homes and tree-lined streets. The bridge has beautiful views of Charleston Harbor and is one of my favorite places for group photos.

Stop at The Co-Op for a glass of frosé before heading to the beach.

Spend part of the afternoon on Sullivan’s Island. Sullivan’s Island is my favorite beach in the Charleston area because it feels relaxed and less touristy than many beach destinations. Bring sunscreen, hats, water, and anything else your group will need because there are no vendors directly on the beach.

If your group wants a little movement, book a private beach yoga class with Serenity Tree Yoga. They can create a personalized, all-levels class for your group on Sullivan’s Island, complete with the sound of the waves in the background. No one needs to be an experienced yogi, and they can help arrange towel or mat rentals if you do not want to pack your own. It is such a fun and peaceful girls’ weekend activity before brunch and a day at the beach.

When everyone is ready for lunch, head to The Obstinate Daughter. Its menu focuses on wood-fired pizza, pasta, small plates, and seafood, and the atmosphere is perfect for a girls’ afternoon. Reservations are strongly recommended.

After lunch and a little more beach time, return downtown and get ready for your final night out.

Begin with rooftop drinks at Citrus Club. Located on the eighth floor of The Dewberry, Citrus Club has beautiful views of Charleston’s steeples and skyline. Make a reservation, especially if you are traveling with a larger group.

Finish the evening with dinner at The Ordinary. This upscale seafood restaurant is housed inside a former bank on King Street. Order several dishes to share, or fully commit to one of its impressive seafood towers. You will want to make this reservation well in advance.

If no one is ready for the night to end, stop at La Cave for a nightcap. This intimate French lounge on Upper King Street feels like a glamorous little escape to the South of France. It has dramatic arches, chandeliers, cozy banquettes, French wines, craft cocktails, rare whiskies, and French-inspired small plates. It is the perfect place to squeeze in one last fancy drink together.

Monday: Take One Last Charleston Lap

If you have time before your flight or drive home, use Monday morning for one final walk, a meaningful souvenir, and a great Charleston lunch. From The Isla Suite, you can do this final lap on foot.

Walk to Bad Bunnies Coffee for your first coffee of the morning. This specialty coffee shop is owned by local husband-and-wife artists Rick and Carol, who are every bit as adorable as the shop itself.

Rick used to draw two little bunny characters on the love notes he left for Carol, and those notes eventually inspired the name Bad Bunnies. Look around while you are there because some of the original bunny love notes have been incorporated into the shop’s decor.

Next, stop at Huriyali for smoothies, açai bowls, and a healthy breakfast. Its colorful courtyard is a refreshing place to recover after a weekend filled with cocktails and incredible meals.

Visit HART Jewelry and make matching charm necklaces to remember your girls’ weekend. Everyone can choose a chain and the charms that feel most meaningful, and the jewelry is assembled for you in the store.

If you are traveling with a larger group, contact HART in advance to ask about reserving its private event room. There is typically no additional fee for the room, but confirm the current details when arranging your group experience.

Have one final Charleston lunch at Leon’s Oyster Shop. Leon’s is casual, lively, and housed inside a converted auto body shop. It is known for fried chicken, oysters, excellent salads, frozen gin and tonics, rosé on tap, and soft serve. The laid-back atmosphere makes it the perfect place for one last celebratory meal before everyone heads home.

Then it is time to collect your luggage, say goodbye to Charleston, put on your new matching necklaces, and start planning your next girls’ trip.

Book Your Girls’ Weekend in Charleston

The Isla Suite is the suite we recommend most often for a girls’ weekend. It has four bedrooms, two bathrooms, a first-floor location, and access to the backyard. Best of all, you can walk to coffee, cocktails, and dinner.

If your group needs more room, add The Poppy Suite upstairs in the same house. Together, the two suites allow everyone to stay in one place without feeling crowded.

You can see all seven of our downtown Charleston vacation rentals and book directly with us.