A Weekend in Charleston, South Carolina !!

The Carry On Twins Guide to the Perfect Long Weekend

Charleston is one of those cities that somehow has it all—historic streets, beautiful beaches, incredible food, boutique shopping, and some of the best nightlife in the South. Whether you’re planning a girls’ trip, a romantic getaway, or a long weekend with friends, Charleston is the kind of place you’ll want to come back to again and again.

After spending a weekend here, we’ve put together exactly how we’d recommend experiencing Charleston for the first time.

Our biggest tip? Stay downtown.

While we loved spending time on Folly Beach, we’d recommend booking a hotel in Historic Downtown Charleston. You’ll be within walking distance of King Street, restaurants, coffee shops, rooftop bars, and all the city’s charm—and the beaches are only about a 20–30 minute drive away.

Where We’d Stay

📍 Historic Downtown Charleston

Staying downtown lets you walk almost everywhere, then take easy day trips to the beaches when you want a slower pace.

Friday | Beach Day at Folly Beach 🌊

Morning

Start your morning with coffee before heading to the beach.

Our Favorites

☕ Dead Low Coffee📍 113 E Ashley Ave

☕ Center Street Coffee📍 103 E Cooper Ave

Both are perfect for grabbing coffee and breakfast before a beach day.

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Beach Time

Spend the afternoon relaxing on Folly Beach. Instead of packing chairs and umbrellas, rent them from one of the local beach rental companies. They’ll have everything waiting for you when you arrive, making your beach day completely stress-free.

Bring:

• Beach towel

• Sunscreen

• Book

• Water

• Camera

Lunch

• Chico Feo

One of our favorite laid-back lunch spots with tacos, outdoor seating, and the ultimate Folly Beach atmosphere.

or

• Taco Boy

Tacos, margaritas, and beach vibes—what more could you ask for?

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Girls’ Dinner Spotlight

Pinky’s on the Beach

If we could only recommend one dinner on Folly Beach…

It’s Pinky’s.

Think:

🌸 Pink umbrellas

🍹 Frozen cocktails

🌊 Ocean views

✨ The cutest girls’ dinner you’ll have all weekend.

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Optional Sunset Stop

Before heading back downtown, stop by:

📍 Bowen’s Island Restaurant

Fresh seafood, oysters, marsh views, and one of the prettiest sunsets near Charleston.

Saturday | Explore Historic Charleston

Start your morning downtown before wandering the historic streets.

Spend time exploring:

• Rainbow Row

• Waterfront Park

• Pineapple Fountain

• The Battery

One of our favorite things about Charleston is that there isn’t a rush. Wander down side streets, admire the colorful homes, and pop into local boutiques—you’ll stumble upon some of the city’s best hidden gems.

Shop King Street

You could honestly spend an entire afternoon shopping here.

Our favorite stores:

• 🎀 Stoney Clover Lane

• 🌸 LoveShackFancy

• Roller Rabbit

• 🤍 Brandy Melville

• 🎨 Rebecca Illustrated

• 🌊 Quiet Storm Surf Shop

• SKIMS

• 📚 Sweeter Than Fiction

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Lunch

Some of our downtown favorites include:

• 🥗 The Daily

• 🥪 Basic Kitchen

• 🦪 167 Raw

• 🍕 Melfi’s

All are fantastic spots to recharge before more exploring. 

Dinner

✨ Ritual Rooftop

We absolutely loved the atmosphere here. It’s one of Charleston’s most popular rooftop restaurants with incredible city views, seafood, cocktails, and a fun energy that transitions into nightlife later in the evening.

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Charleston Nightlife

If you’re not ready to call it a night…

Here are our favorite spots:

• ✨ Madison Maison

• 💃 Trio

• 🌴 Ritual Rooftop Restaurant & Lounge

• 🥂 The Belmont

• 🎷 Prohibition

Whether you’re looking for rooftop cocktails, dancing, or live music, Upper King Street comes alive after dark and has something for every kind of night out. 

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Sunday | Sullivan’s Island Day Trip

If you have one more day, we’d recommend exploring Sullivan’s Island.

It’s quieter than Folly, has gorgeous beaches, and feels a little more local.

Spend your morning:

☕ Grab coffee

🚲 Walk the beach

🌊 Swim

📖 Read a book

🍹 Enjoy a slow afternoon

Lunch

Some of our Sullivan’s Island favorites:

• 🍔 Poe’s Tavern

• 🐟 Obstinate Daughter

• 🥪 The Co-Op (don’t leave without trying the famous frosé!)

Charleston Weekend Itinerary

Friday

• Coffee on Folly Beach

• Beach day

• Chico Feo

• Pinky’s

• Sunset at Bowen’s Island

Saturday

• Historic Charleston

• King Street shopping

• Lunch downtown

• Ritual or Maison

• King Street nightlife

Sunday

• Sullivan’s Island

• The Co-Op

• Beach

• Head home

Carry On Twins Tips ✈️

🤍 Stay downtown and drive to the beaches—you’ll experience more of Charleston while still getting plenty of beach time.

🤍 Rent beach chairs and umbrellas instead of bringing your own. It’s one of those little upgrades that makes the whole day feel like vacation.

🤍 Leave room in your itinerary to wander. Charleston’s charm is found in its hidden courtyards, colorful homes, and local boutiques just as much as its famous landmarks.

🤍 If you’re only shopping one place, make it King Street. It’s packed with everything from iconic brands to local boutiques you’ll only find in Charleston.