When Travel + Leisure’s “World’s Best” awards came out in 2017, 2018 and then AGAIN in 2019, I wasn’t too shocked to see Charleston top the list three years in a row, stealing the 1st place spot  in the “Top Cities in the United States.” I’ve spent the last 10 years getting to know this little town (thanks to having family who reside there) and am glad that Travel + Leisure loved it as much as I do. Therefore, I’ve decided to gather up everything I know about the Holy City (as its known) and create a guide to help you see the best of South Carolina’s claim to fame in just a weekend.

Note: Most of these activities are COVID-19 friendly however not all of them may still be open/operating under normal business hours during this time so be sure to do your research 🙂 

Things to Do

Although beach time is a must in the summer, a lot of Charleston’s charm and adventure lies off the sandy shores. Get out and explore what the city has to offer:

Get Lost Downtown:

The absolute best way to explore Charleston is to literally get lost. Meander down the side streets of downtown and marvel at the amazing houses this city has to offer. All different colors, shapes and sizes, squished together with rows upon rows of perfect window boxes and peaks into private courtyards.

• King Street: As you get lost downtown you are sure to wander upon King Street – the heartbeat of the city. This street is literally packed with restaurants and all of the best shopping. Because of this, it’s also usually packed with tourists, especially in the summer months.
• Battery Park: If you’re picturing Charleston as Spanish moss dripping off the splayed branches of centuries-old oak trees, this park is the place for you. Complete with a rotunda in the middle, the perfect spot for taking pictures or a surprise engagement. Bonus – there is free parking here! If you have driven into town this might be your best bet for free street parking in the city.
• Rainbow Row: Probably what Charleston is known for most is this row of colorfully painted houses that sit on East Bay Street facing the Charleston Harbor. Painted in hues pastels due to the city’s Barbados influence, these houses have withstood for centuries and serve as a lovely backdrop for photo sessions.
• Market Street: Market Street is a must for first-time visitors (and those who can’t stop coming back 10 times later like me!) and an ideal place to pick up souvenirs. The markets sell everything from handmade jewelry and local artwork to woven Sweetgrass baskets.
• Waterfront Park: Looking for the wind on your face, salt in the air, and a pineapple shaped fountain? Head to the Waterfront Park! Swing on benches on the pier, run through fountains on a hot day, and look for dolphins in the Charleston Harbor.

Ghost Tour:

Charleston is a town full of history, charm and ghosts! It’s haunted past makes for a plethora of ghost tours that start at twilight every night of the week.

Sullivan’s Island:

My favorite little hideaway! Get ready to slow down and explore the island that inspired the setting for Edgar Allen Poe’s “The Gold Bug.” Sullivan’s is the perfect place to watch the sunset behind the city as it’s just across the harbor. Make sure to grab some food from the line of local restaurants on Middle Street. P.S. my favorites are Poe’s Tavern and Mex 1!

Charleston Harbor:

Looking for a water adventure? Get out in the Harbor! Rent a boat, do a dinner cruise, or take a tour of Fort Sumter.

Shem Creek:

What do beer, seafood, and water sports have in common? The obvious answer – Shem Creek! Rent a kayak or paddle board and explore the inner coastal (dolphins and manatees are known to explore this area too). Or grab a drink after dinner at Red’s Ice House or Saltwater Cowboys. Have your own boat? Pull up and tie off on the docks that line the restaurants’ waterfronts.

A list of the best food spots and watering holes in Charleston could go on and on. So I’ll just sum it up with a few of my favorites!

Poogan’s Porch:

At first glance, Poogan’s could be any other darling yellow house down one of Charleston’s side streets. This spot has gained immense attention since being named in Travel + Leisure’s Charleston article, but it’s been around serving low country food long before the city took first place in the magazine’s “World’s Best” and is my absolute favorite spot to grab brunch!

The Darling Oyster:

A trendy brunch spot with $4 mimosas and lobster claw Bloody Marys, do I need to say more?

5Church Charleston:

Ever dreamed of indulging in alcoholic beverages while at church (just me…?) Now you can! This church turned restaurant/bar has a wide variety of drinks and is right on Market Street.

The Vendue:

This hotel right on Charleston’s waterfront doubles as a rooftop bar. Head over for drinks at sunset and watch East Bay Street from above come to life with restaurant goers and bachelorette parties.

Upstairs at the Skinny Dip

This trendy bar and coffee shop will have all of your Instagram dreams coming true. The space includes an outdoor patio, cute murals, and even serves frose. It sits on top of a clothing boutique named the Skinny Dip which you must walk through to find the stairs that lead you up.

Charleston is bursting with things to do, places to see, and seafood to try… this is just a small glimpse! A weekend trip (read: no PTO needed) is the perfect amount of time to get a taste of South Carolina’s jewel.

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