The Perfect 5 Day Charleston Itinerary for First-Time Visitors

Few cities are as easy to fall in love with as Charleston, South Carolina.

I moved back and forth from the area over 4 years and have visited countless times of since. After all the places I’ve traveled, Charleston still leaves me wanting more.

I’ve laid out this 5 day Charleston Itinerary highlighting all my favorite places and things to do. When you’re through with your trip, I hope you love Charleston as much as I do!

Day one:

For your first day on your 5 day Charleston itinerary, you’ll stay near Mount Pleasant in the morning and head downtown in the evening.

Morning – 0800 – 1100

Grab an iconic southern breakfast at Pages Okra Grill
Walk the Shem Creek boardwalk & look for dolphins

👉 Consider taking this Shem Creek Walking Tour, starting at 1000

Afternoon – 1200 – 1500

Explore the scenes of Outer Banks on this e-bike tour – then grab lunch and drinks in Mount Pleasant at Salt Water Cowboys (best waterfront atmosphere). Alternatively, head over to Isle of Palms for some beach time if the weather is nice!

Late Afternoon – 1500 – 1700

Head to Boone Hall (closes at 1700) to learn more about Gullah culture, black history and insight on slavery in the United States.

Evening – 1700 – sleep

For sunset – head to Pitt Street Bridge and view the Charleston skyline. Then choose between staying local and heading downtown to Upper King Street.

👉 Mount Pleasant: The Post House for dinner and then walk to the Gala Cafe and Bakery for dessert and drinks.

👉 Downtown: It’s hard to go wrong on Upper King, but explore delicious restaurants like Malagon, Vern’s, Sorghum and Salt, or the Darling Oyster Bar. If you feel like staying out for drinks and dancing some options are: The Republic, Prohibition, Uptown Social (generally younger crowd) or Charleston Beer Works. The Cocktail Club was a favorite of mine too!

Day two:

You’ll make a quick stop downtown today, then cross the bridge to West Ashley and come back again downtown.

Morning – 0800 – 0900

Wake up and grab coffee and baked goods at Welton’s Tiny Bakeshop

Early Afternoon – 1000 – 1400

Head to Magnolia Plantation gardens or Middleton Plantation to enjoy nature and historic buildings

Late Afternoon – 1500 – 1800

Consider waiting in line for the iconic Chubby Fish – or dropping someone from your party off and exploring Upper King further

Evening – 1900-2100

Shop, drink and dance along Upper King or head back to Mount Pleasant and hang out at Red’s on Shem Creek (check the live music schedule)

Late evening – 2100

If you’re over food and drinks, join this Nighttime USS Yorktown Tour in Mount Pleasant

Day three:

Charleston is a walking destination – You’ll have plenty of walking to do today, so where your walking shoes!

Morning – 0800 – 1000

Take a morning stroll along Sullivan’s Island – bonus, bring your dog!
Grab a coffee or frosé from the iconic Co-op, or grab weekend brunch at the Obstinate Daughter

👉 Learn more about the best beaches in Charleston, SC

Early Afternoon – 1100 – 1330

Drive to the Charleston Market and shop around (best on weekends but always good)

Late Afternoon – 1330 – 1700

Check out this downtown walking tour – highly recommend! After, shop away on Upper and Lower King street – the streets open up to pedestrians on Second Sunday (until 1700) if you happen to be in town

Evening – 1800 – sleep

Try Hank’s Seafood or Poogan’s Porch for dinner – there’s many good spots near this area
Don’t miss out on Kaminsky’s Dessert Bar after dinner

👉 Check out my Where To Eat in Charleston guide

Day Four:

Now that you’re four days in on your five days Charleston – take your time this morning, grab some delicious food for lunch, then consider getting on the water. End your evening with show or carriage ride.

Morning – 0800 – 1100

Now that you’ve done the formal walking tour, take your time and walk from the Pineapple Fountain to The Battery, through Rainbow Row and up church street. Admire the architecture and classic flower baskets.

Early Afternoon – 1100 – 1300

Grab lunch at 167 Raw – best to put your name in as close to 1100 as possible, as it develops a wait list quickly. If you have non-seafood lovers in your group, check out their sister spots Bar 167, which has both seafood and non-seafood dishes.

Late Afternoon – 1400 – 1700

Take the boat tour to Fort Sumpter, or if you want less of a history experience, choose the Charleston Harbor Bar Pedal Boat Cruise

Early evening – 1800

Grab a family-style dinner at Lewis BBQ – get the brisket!

Evening 2000 – sleep

Check out the local event schedules – Theatre 99 has improv shows every Wed-Saturday at 8pm. Alternatively, consider this night time haunted carriage ride

Day Five:

You’ll drive around a bit more today. Start this morning in Mount Pleasant again, but then cross through downtown to John’s Island. Before you return back to the hotel, you’ll head to Isle of Palms.

Morning – 0700-0900

Grab breakfast at Vicious Biscuit
Walk the Ravenal Bridge (about 5 miles total or 2.5 to the top and back)

Early Afternoon – 1000 – 1500

Venture to Charleston Tea Plantation, Deep Water Vineyards and the Angel Oak Tree on John’s Island

Late Afternoon – 1600

Early dinner at Acme Lowcountry Kitchen in Isle of Palms and then watch sunset at the beach

FAQ –

Where to stay when visiting Charleston?

I recommend staying in Mount Pleasant as there is plenty to do here and cheaper than staying downtown. You’re also more likely to avoid flooded roads if it’s raining (downtown floods easily). But it keeps you close to the action of downtown as well.

Where to fly into?

You should fly into Charleston International Airport (CHS). It’s about a 20-40 minute drive toward Charleston depending on traffic and the location you’re staying in.

Do you need a car?

Yes, you will likely need to rent a car for this itinerary.

What is the best time of year to visit Charleston?

Charleston is a year-round destination.

Spring (March – May) and fall (September – November) offer the best weather and fewer crowds.

Overall, summer is hot and humid, while winter is quieter and cooler. If you’re looking for a December getaway, check out more about Charleston in December

Well… Why should you use this 5 day charleston itinerary?

Charleston feels like a second home to me. While it’s a popular destination, it’s also a place locals genuinely love living in. The goal of this itinerary is to help you experience Charleston through a local perspective, while also highlighting experiences that make the city so well known.

This itinerary highlights the places and experiences I grew to love during my time there – and now I’m sharing them with you! This itinerary balances the must-see historic sights with great food and enough flexibility to slow down and explore further.

Hi, I’m Amber —

A Michigan native now living in Washington with a deep love for travel and the outdoors. What started with church mission trips and traveling across the U.S. as a nurse has grown into a passion for exploring the world through hiking, food, culture, and the beauty of God’s creation. Sometimes I’m joined by my goldendoodle, Millie, but I’m always traveling with my camera. My goal is to help you feel inspired and confident that travel is possible — no matter where you’re starting from.