Being in the business of real estate and luxury vacation rentals, when our guests are headed to the Holy City, whether for business or for pleasure, our team is frequently asked, “What should be on our ‘must do” list while we’re in Charleston?” And, while everyone’s idea of the perfect vacation in Charleston SC is different, whether it’s for the history, the food, the architecture or just soaking up some sun on the beach, there are indeed some distinctly Charleston things to see, do and experience. That’s why we’re kicking off the New Year by sharing a “Top 20 Bucket List” of the things you’ll definitely want to do while you’re here – from grandiose adventures to simpler, thought-provoking experiences and even just an iconic place or two to snap a selfie. So, if you’re visiting for only a weekend, a week, or are a longtime local with family & friends in town experiencing Charleston’s charms for the very first time, keep this list handy and challenge yourself to check-off as many as you can!

The Top 20 Charleston Bucket List

1) Sit in Washington Square on a Sunday morning

Tucked alongside the “Four Corners of Law,” where Meeting Street intersects with Broad Street, this breathtaking park pays tribute to George Washington and includes a miniature version of the Washington Monument (the original is in Washington, D.C.). On Sunday mornings, you are in earshot of church bells from at least five parishes that date back centuries in Charleston.

2) Visit Charleston’s Halsey Institute of Contemporary Art

With an international artist-in-residence program and exceptional caliber of exhibits curated by the museum staff the Halsey is a “must see.” Admission to the gallery is free.

3) Go paddle boarding or kayaking on Shem Creek

Shem Creek is a scenic waterway offering panoramic views of the marsh and Charleston Harbor and has been considered home to Charleston’s once flourishing shrimping fleet for nearly a century. It is the epicenter of Mount Pleasant’s trendy waterfront dining district, and includes a park and 2,200 foot long boardwalk. This is a popular spot for boaters, paddle boarders and kayakers alike and most days, you’re certain to share the creek with a dolphin or two!

4) Train your Dog to jump off a Dock

How else will Fido be ready to compete in the wildly popular “Dock Dogs” event during the Southeastern Wildlife Expo (SEWE) that happens every February in Charleston?

5) Take a ride in a PediCab bike taxi

No need to call an Uber if it’s just the two of you! Hail a pedicab and relax while you experience the sights and sounds of the Holy City and your friendly pedicab driver does all the peddling!

6) Attend a Barn Jam at Eddie White’s Awendaw Green

The Awendaw Green Barn Jams are an outdoor, year-round Wednesday night original music showcase that connects folks who appreciate local, original music with others and supports the artists that make it. It runs from 6-10pm every Wed night of the year and features a diverse assembly of music from around the globe. Try a wood fired pizza, the grill, or fresh local oysters in season and drink your own BYOB libations.

7) Explore Bull’s Island

This “best kept secret” is something that even many local Charlestonians haven’t crossed off their own bucket lists.  Located just 30 minutes north of the city, Bull’s Island is one of the crown jewels of Cape Romain National Wildlife Refuge. Don’t forget hiking boots or walking shoes (not flip-flops), a hat & sunscreen, then take the Bulls Island Ferry and explore some of the 16 miles of trails and roads including 7 miles of undeveloped shoreline to connect with nature and yourself.

8) Walk the Ravenel Bridge

Lace up your shoes, grab a friend and head to The Arthur J Ravenel bridge which spans the Cooper River between downtown Charleston and Mount Pleasant. The bridge offers stunning views of Charleston Harbor and is 2.5 miles long with a dedicated walking/running/biking path protected from traffic with a concrete barrier.

9) Take a Brewery Pub Tour

With Charleston’s ever growing list of craft brew houses, you just might need more than one day if you plan to taste your way through them all!  You’ll find brew pubs located all around the Charleston area, from the downtown peninsula, to Mt. Pleasant, Daniel Island, and even West Ashley!

10) Cheer on the Charleston Riverdogs

There’s a reason why they call baseball “America’s favorite pastime,” and from Memorial Day to Labor Day there is simply nothing like spending a summer evening at a Charleston Riverdogs game. Head to Joe Riley Stadium, located in downtown Charleston along the banks of the Ashley River.  You can grab a hotdog, a cold brew and who knows – you might even catch a glimpse of co-owner Bill Murray sitting behind home plate!

11) Explore the Maritime Forest on Sullivans Island

Sullivans Island made a bold decision long ago, that the best way to protect their beloved shoreline was to allow the natural vegetation to grow wild in hopes of shielding the dunes from the high winds and storm surge of coastal storms.  The resulting Maritime Forest is hauntingly beautiful and provides a home for island flora and fauna.

12) Rent A Bike from Holy Spokes for the day and peddle through all of the distinctive neighborhoods on the Charleston Peninsula

Start in the enchanting South of Broad neighborhood, then peddle through The French Quarter, Harleston Village, Ansonborough, Radcliffeborough, Cannonborough-Elliottborough, Upper King, East Side, West Side, and North Central. The neighborhoods that make up Charleston’s downtown historic district each offer a unique vibe all its very own.  Holy Spokes

13) Take a Ghost Tour

Founded and settled by English colonists in 1670, Charleston has a rich and colorful history.  And in a city as old as Charleston, you’re sure to discover there’s more than one, haunting ghost story around. From graveyards to the Old Jail and a neighborhood filled with haunted mansions, you can choose from a variety of nightly tours that will take you to many of Charleston’s most infamous and haunted sites and undoubtedly send a chill up your spine.

14) Spend a Morning in Mount Pleasant’s Old Village
Take a stroll along the Pitt Street Bridge, soak in the Charleston skyline and harbor views from the grounds of Alhambra Hall, and have a milkshake at the soda fountain of Pitt Street Pharmacy.

15) Take a trip to “Boneyard Beach” at Botany Bay on Edisto Island, and walk through the “boneyard’ of dead trees

Erosion on Botany Bay Beach has left a “boneyard” of dead trees along the sand, creating a starkly beautiful coastline like you’ve never experienced before.  The best time to visit the beach is at low tide when a wider section of the shoreline is exposed.

16) Take a boat tour of Charleston Harbor

The Holy City is beautiful from nearly every angle, but if you haven’t experienced the skyline from a boat in the Harbor, you’re missing one of the best views.  Whether you book a dinner cruise on the Spirit of the Carolina,  have cocktails aboard a sailing yacht at dusk, or power you way through in a sleek speed boat, this is an experience you don’t want to miss.

17) Attend an Oyster Roast

Although there is an oft-recited piece of advice about oysters: Only eat oysters in months that contain the letter “R” in the name. You know, September, October, November, December, January – not June, July, August – we can tell you that anytime is a good time for a lowcountry oyster roast.  And while it’s true they are more popular in the winter months, around Charleston you can find a good oyster roast pretty much anytime of the year.

18) Take a picture by the Pineapple Fountain in Waterfront Park

Charleston’s Waterfront Park is one of the best locations in Charleston to experience the charm and hospitality of this coastal city, and that includes a fountain in the shape of a pineapple.  No visit to Charleston is complete without a picture next to this iconic landmark.

19) Sip a Cocktail on a Rooftop bar at Sunset

When city views include the Atlantic ocean, a busy harbor, historic centuries-old church steeples and the architecturally stunning Ravenel Bridge, you definitely want to experience them all from a posh rooftop bar.  Charleston has many to choose from including The Rooftop at the Vendue, Pavilion Bar at the Market Pavilion Hotel, the Rooftop Bar at Henry’s, The Watch Rooftop Kitchen & Spirits at the Restoration Hotel and Élevé Rooftop Restaurant & Lounge at the Grand Bohemian Hotel.

20) Take a day trip to Charleston Tea Plantation 

There are many tea plantations around the world, located in far away destinations like Asia, Africa and South America, making Charleston Tea Plantation the only one you can experience without needing a passport! Located on Wadmalaw Island, one of Charleston’s scenic sea islands, here you can see hundreds of thousands of tea bushes stretching out acre after acre for almost as far as the eye can see.


And remember, If you don’t make it through checking everything off the Top 20 Charleston Bucket List all in one visit, it will give you the perfect reason to plan a return trip to Charleston … not that you need one.  Our Retreats Concierge team is here to help you plan the perfect itinerary for you to experience the best of Charleston for yourself!