The Ultimate 4-Day Charleston Girls Trip Itinerary

While my usual travel content revolves around family road trips with my three kids, every mom knows that a recharge trip with your best girlfriends is absolute magic for the soul.

When my girlfriends and I started planning our annual getaway trip, Charleston, South Carolina immediately rose to the top of our list. It has the perfect mix of everything: rich Southern history, cobblestone streets, incredible food, rooftop cocktails, and easy access to lots of outdoor adventures.

We packed four days full of historic sights, beach time, ghost tours, and top-tier shopping and dining. If you’re looking for some inspiration for your next girls trip, here is our 4-day Charleston girls trip itinerary that you should absolutely steal.

Trip at a Glance & Quick Travel Logistics

• Transportation: Flew in and picked up a rental car right at Charleston International Airport (CHS). While downtown Charleston is walkable, having a car gave us the flexibility to drive out to Cypress Gardens, take a plantation tour, and spend some time exploring cute beach towns like Isle of Palms.
• When to visit: We visited Charleston during mid-September, which is still peak summer weather. Our days were very humid and hot, which are great for beach time. If you are looking for cooler temps with less humidity, I would recommend late fall or early spring.
• How long do I need: We found 4 days to be the perfect amount of time to explore Charleston and the surrounding areas.

Day 1: Swamps, History, & a Sunset Champagne Sail

Morning: Cypress Gardens & Boat Paddle

We kicked off the first day of our Charleston girls trip early by heading to the Cypress Gardens. This charming garden is located about 30 minutes from downtown Charleston, and has been made famous because it’s one of the iconic filming location for The Notebook.

The entrance fee is $10, and that includes a self guided rowboat paddle through the cypress swamp. I highly recommend this activity – it was so much fun and perfect for a Charleston girls trip!

• Pro Tip: Arrive right at 9:00 AM when they open to beat the mid-day heat, avoid crowds, and catch the best light through the trees.

Afternoon: Middleton Place Lunch & Tour

Next, head to Middleton Place for lunch and a historic plantation tour. The property features America’s oldest landscaped gardens, stunning oak avenues overlooking the Ashley River, and deep historical exhibits.

The onsite restaurant offers beautiful views of the garden and a great variety of food and drinks.

Evening: Private Sunset Sail & Board on the Water

For the ultimate Charleston girls trip kick-off, I highly recommend taking a sunset boat tour through the Charleston harbor. We booked this tour on a private sailboat, and had such an amazing time touring Charleston by sea.

Before heading to the marina, we picked up a custom charcuterie board and some champagne from Caviar & Bananas, which made for the perfect dinner on our sailboat.

Sailing across the harbor with a glass of champagne, watching the sun dip below the Charleston skyline, and seeing the dolphins splashing around our sailboat was an absolute highlight of the trip.

Afterward, we made the 40-minute drive over to Isle of Palms (IOP) to settle in near the beach for the night.

Where to stay:

I highly recommend a cozy beach house on the Isle of Palms for the next 2 nights!

We stayed in this lovely 2 bedroom beach house that offered a full kitchen, 2 bathrooms and was a quick walk to the beach.

Day 2: Beach day at Isle of Palms

Morning: Classic Island Brunch

We slowed down our pace and spent Friday enjoying the coastal side of Charleston. We started with breakfast at Sea Biscuit Cafe on Isle of Palms—a cozy, long-standing local favorite known for incredible biscuits, crab cake benedicts, and Southern hospitality.

Then we headed to the beach, where we rented beach chairs and spent the morning relaxing and soaking up the sunshine.

Afternoon: Beach Relaxation & Frosé Flights

After a relaxing morning on the sand exploring the IOP beach, we stopped for a casual lunch at The Outpost before making the ultimate Charleston beach stop: The Co-op.

You cannot visit Isle of Palms without getting a frosé flight at The Co-op! They are famous for their rotating gourmet frozen rosé flavors and hilarious, tongue-in-cheek atmosphere. It is the quintessential Charleston girls’ trip stop!

Evening: Oceanside Dinner

We wrapped up our beach day with a laid-back dinner at Coconut Joe’s Beach Grill, enjoying rooftop ocean views, tropical drinks, and delicious seafood.

Read more about our day on Isle of Palms here

Day 3: Historic Highlights, Rooftops, & Haunted Pubs

Morning: Charleston Farmers Market

We headed back into downtown Charleston to kick off Saturday at the Marion Square Farmers Market, grabbing fresh local coffee and breakfast sandwiches while browsing local artisan stalls.

Midday: Citrus Club Rooftop Drinks

After spending our morning at the Farmer’s Market, we headed to the Citrus Club, a stunning rooftop bar located atop The Dewberry hotel. It offers the highest rooftop views in the city and the cutest and most colorful citrus cocktails. It’s the perfect spot for a drink and bite before heading off to explore more of Charleston.

From there, we took a self-guided walking tour through some of Charleston’s most historic landmarks:

• Pineapple Fountain at Waterfront Park
• Washington Square
• Rainbow Row (the famous pastel-colored historic homes)
• The Battery & White Point Garden for sweeping harbor views under giant live oaks
• Historic City Market for local souvenirs

You could also take a historic carriage tour through downtown Charleston.

Evening: Church & Union, Desserts, & a Haunted Pub Crawl

For dinner, we had reservations at Church & Union, a striking restaurant housed inside a converted 100-year-old church with handwritten text from The Art of War painted across the entire ceiling. The food and energy here were amazing!

After dinner, we strolled over to Carmella’s Cafe & Dessert Bar for gourmet cake slices and coffee before meeting up for a Haunted Pub Crawl.

Charleston is known as one of America’s most haunted cities, and pairing local ghost folklore with a couple pub stops was such a fun nighttime activity for a Charleston girls trip. You could easily replace this with a family friendly ghost tour if visiting Charleston with kids instead.

We ended the night grabbing a final drink at Camellias, the iconic pink champagne bar inside Hotel Bennett.

Where to stay:

I recommend staying in downtown Charleston for your final night. It puts you close to activities for both today and tomorrow. We stayed at the Lowline Hotel – which had a really fun and moody vibe, plus onsite coffee and dining.

Here are some other suggestions:

• Hampton Inn Charleston – family rooms + free breakfast
• Francis Marion Hotel – boutique hotel with restaurant & spa; budget friendly
• The Nickel Hotel – great location, balconies, + free bikes for guests use

Day 4: Sunday Brunch & King Street

Morning: Poogan’s Porch Brunch

No Charleston trip is complete without a traditional Southern Sunday brunch. We dined at Poogan’s Porch, a legendary spot set inside a gorgeous Victorian home. I highly recommend their chicken & waffles – so good!

Afternoon: Second Sunday on King Street Shopping

We lucked out because our final day aligned with Second Sunday on King Street. From noon to 5:00 on the second Sunday of every month, King Street is closed off to vehicle traffic. The street transforms into a giant pedestrian avenue filled with outdoor dining, live music, street performers, and shopping.

It was the absolute best way to spend our final hours in Charleston before heading to the airport. Even if your trip doesn’t coincide with Second Sunday, I highly recommend spending your final afternoon walking up and down King Street to explore all the shops.

Final Thoughts: Should you Plan a Charleston Girls Trip?

100% yes. Charleston offers the perfect balance between relaxing coastal vibes and rich, walkable city energy. Whether you want to dress up for rooftop cocktails, dig into Southern history, or just laugh over frosé by the beach, this city delivers on every front and is the ultimate girls trip destination.

Read Next:

• Ultimate Guide to Spending a day on Isle of Palms
• [What to do in Charleston with Kids]