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Charleston, SC: 5 Day Itinerary

We visited Charleston, South Carolina this past fall. The slower pace of this beautiful and historic city in South Carolina is perfect for a family vacation, a romantic getaway, or a weekend with friends. We recently spent five days in Charleston and loved every minute of it.

Below is the five-day travel itinerary from our trip. We filled our days with the perfect balance of history, sightseeing, and relaxation. Follow our itinerary, complete with links, to enjoy your own Charleston getaway.


Lunch and Shopping at the City Market

Self-Guided Walking Tour

Dinner & Drinks


Lunch and Shopping along King St.


Magnolia Plantation Tour and Swamp Trail

Angel Oak

Lunch and beach at Folly's Beach


Old Exchange and Provost Dungeon

Shem Creek Boardwalk - dolphins and lunch

Isle of Palm

Dinner & Drinks


Fort Moultrie

Charleston Lighthouse on Sullivan Island


Travel Home

Know Before You Go:

  • Dinner reservations during high tourist times are a must.

  • There are so many fun places to stop for live music, cocktails, dessert surrounding the City Market. We were able to walk into the rooftop bar and find seating and a waitress!

  • Wear comfortable shoes! Historic Charleston is all about walking and the streets are uneven.

  • Take full advantage of my love of travel and planning skills, connect with me here to book your travel and/or free quote for my planning services.

When to Go:

In our opinion the best time to visit Charleston is March to May or September to November. The temperatures are lovely - typically 60-80 degrees – without the humidity and heat of the summer months.

Is Charleston Safe?

Yes! Charleston is considered safe for visitors. However, Charleston is a city, so we recommend taking the typical city precautions – don’t walk alone at night, park your vehicle in well-lit locations, ensure valuables are stored out of sight, be aware of your surroundings.

Getting Around:

We recommend using a rental car. For our adventures in Charleston, we loved having a jeep wrangler. It was a treat! Parking isn’t a problem if you know where to look. A full list of parking options can be found at Parking Information. This link includes parking locations, costs, as well as amenities like security or restrooms. We found both the Waze app and Google maps to be easy to use to navigate from one destination to another.

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