Downtown Charleston is a constant and fabulous bustle of immense history, shopping, culture, great architecture, art, world class dining and nightlife. For that reason, we could not possibly justly serve all of the possibilities and ideas for downtown fun. We will however offer up a minimal few of our personal favorite guest or “staycation” days.
Mt. Pleasant to Downtown, A Family Day (Tour #1)
A day is best started with breakfast at Mt. P’s Page’s Okra Grill, southern food at its best. If you’re looking for something more casual or light, try Collective Coffee in Mount Pleasant, known to coffee enthusiasts with casual but super yummy breakfast fare.
While at the Aquarium, be sure to buy a ticket for the Sea Turtle Rescue Hospital.
After the Aquarium, smaller kiddos will be ready to head back, but for the crowd with more energy, take a rickshaw or pedicab ride to Fleet Landing for lunch. Alternative nearby “market walking distance” casual family eating restaurants include Bubba Gump’s and Toast.
Side note, typically the easiest way to find a rickshaw or pedicab is to simply glance down the street, they are everywhere. In the event you’re not seeing one, here are links to two of the leading companies in Charleston, Charleston Rickshaw and Pedicab Charleston.
After lunch, walk through the Charleston City Market and the side street shops to find a plethora of local goods, talented artists, candy and ice cream shops.
An East Bay walk or pedicab | rickshaw ride back to the water taxi complete this day of water related fun.
Downtown, A Family Day (Tour #2)
A casual lunch at Poogan’s Porch on Queen Street is a sure way to keep even the pickiest stomachs happy. Slightly modified (without the slaw, because kids like it plain) but the Poogan chicken sandwich and macaroni and cheese are always kid friendly favorites.
Walk to the Kapla block Store on N Market Street. Kids and adults alike will enjoy building block structures for a short while until your pre-reserved time has come for Escape in 60. We love a good family fun riddle and escape game. Make reservations in advance. Walking distance from Kapla to Escape in 60 is just over 5 minutes.
Walk the open air City Market and visit the shops ending at candy store corner for some sweet treats before ending this easy relaxed day.
Downtown, A City Tour (East Bay, French Quarter)
We can’t say enough about our tour companies of historic Charleston. Whether horse drawn, walking or bus tour, our Charleston tours are a fantastic way to learn about the city.
Here are just a few Charleston tour companies to start your day.
After your tour, head to Cru Café for lunch. “Refined takes on American comfort food served in a charming, old yellow house with a patio.”
Walk off lunch heading down East Bay street to South Broad street and the French quarter area. Take the time to stop at Art Galleries and the beautiful park nooks. Locals and gallery lovers, don’t forget about “First Friday’s on The Row.”
As you are walking back towards the Charleston Market, enjoy rooftop drinks and views at The Vendue or Market Pavilion Hotel.
Downtown, A City Tour (French Quarter and The Battery)
Simplicity is the key to this afternoon. The Charleston Waterfront Park and The Battery are among two of the most beautiful areas and popular downtown walking tours.
If you’ve decided on an afternoon walk, might we suggest lunch first at the casual, oh so French, Gaulart-Maliclet or the popular Brown Dog Deli.
After lunch, enjoy a breezy and beautiful harbor walk at the Charleston Waterfront Park and The Battery.
After your walk, enjoy a delightful recourse sitting at a café table outside of the East Bay Meeting House for a drink, and watching the passers-by.
You can modify this tour if you prefer a sunset walk first, followed by dinner. There is no shortage of restaurant options in this East Bay | South Broad location. Peek at window menus to curb any craving perfectly, but some of the popular suggestions include Oak Steakhouse, Vendue, Blossom, Magnolias, Cypress, Pearlz and Minero. A little farther down East Bay Street is Market Grill, Amen Street, High Cotton, and SNOB.
Downtown, A City Tour (Upper King and Marion Square)
If you happen to be downtown on Saturday am to early afternoon, be sure to swing by the Farmers Market at Marion Square. Food, fresh air, yummy local fare, and the vibe of downtown bustle make it a great start to the weekend.
Upper King is home to incredible restaurants such as Halls Chophouse (their Sunday Gospel Brunch is unsurpassed), Stars, and the Darling Oyster Bar. Equally delicious, but more casual fare can be found at Prohibition, Rare Bit and Little Jacks.
With kids? Visit Jeni’s Splendid Ice Creams and Magnifilous Toy Emporium.
Downtown, A Night on the Town (Entertainment, Food & Drink)
We find it fun to have a food and drink walking itinerary set around a show at one of our many theatres such as The Galliard, Theatre 99 Comedy, Pure Theatre, The Music Farm, and 34 West Theatre Company. Pick any venue and plan surrounding food and beverage accordingly. Below is just one of our itinerary examples.
Start your night with drinks and appetizers at Zero George (their Mixologists are sure to impress).
Take in a show at The Galliard Center.
Enjoy a late dinner at 167 Raw or pedicab | rickshaw to Halls Chophouse
Downtown, A Night on the Town (Bar & Restaurant Hop)
With a plethora of opportunities, even the most critical “foodie” could chose a general vicinity or a restaurant destination and plan some before and after “food sampling and drink fun.” You could plan many a night within the Queen|Meeting|King areas, the Upper King location, NoMo, and the French Quarter|East Bay sphere. Below is an example of one of our favorite “hops.”
Start at Cane Rhum Bar – Begin with starters at this fun and light Caribbean atmosphere that delivers fabulous food and “pain killers” that do the BVI’s proud.
Walk to the nearby Spectator Hotel, this chic and speakeasy influenced bar is one of our favorites for drinks.
Then pedicab or rickshaw to the Darling Oyster Bar on Upper King for a late night dinner (while known for so much scrumptiousness … might we say the french fries with new England clam chowder cannot be missed).
Breeze next door to The Belmont Cocktail Lounge for a final nightcap and a home-made pop tart for dessert.
Side bar … It aches us not to include so many other fabulous fun “hop” evenings and personally mention each and every one of our favorite gems … email us YOUR FAVORITE downtown nights and stomping grounds to Publisher@OccasionsGuide.com.
IOP (A Full Beach Day, The Easy Way)
Spending a day at the beach doesn’t have to be an exhausting proposition of planning and lugging gear. A day prior, arrange for chair and umbrella delivery and set up with IOP Beach Chair.
Before hitting the beach grab breakfast at the Sea Biscuit Café – one of our personal breakfast favorites.
Headed out later in the day? There are several casual lunch favorite restaurants such as Long Island Café and Banana Cabana but we would be remiss if we didn’t note the popular Acme Kitchen conveniently located near the IOP variety beach stores.
Regardless of where you “fill up,” the IOP beach is a place of happy vibes and relaxation. It’s easy to get rattled by the preparation, make it simple and enjoy.
IOP (A Night Out)
Enjoy a sunset beach stroll followed by a delicious Italian dinner at Coda dePesca.
After dinner, whether a continuation of date night or for fabulous group fun, don’t miss the ever popular, Windjammer, Charleston’s original beach club. It’s a great place to see live music!
IOP (Watersports Anyone?)
Not an itinerary, but instead, we wanted to provide you with just some of the water sports fun and rentals available to plan your perfect day. Whether your desire is being in the water, boat rentals, motor or sailboat charter, sunset or dolphin cruise, you can find them here below.
The IOP Marina isn’t just home to their fabulous convenience store and deli … you can rent a boat or plan a charter at the IOP Marina.
Looking for banana boating, wave runners, parasailing, tubing, boat rentals or charters, reach to Tidal Wave Sports.
Looking to rent SUP? Reach to the folks at Ocean Fitness for rentals or tours.
Sail Charleston! For a group or a romantic charter, climb aboard Serena, a 50’ sailing vessel from AquaSafaris and enjoy the beauty of the Charleston waterways. Captain John will show you the stunning barrier islands. You will witness all of the wildlife that the marsh and rivers have to offer. Bring a picnic and a bottle of wine. Captain John with fill the cooler with water, sodas and ice.
After your day is done, don’t forget to swing by Morgan Creek Grill for a beautiful view, afternoon beverage, or bite to eat.
For that full beach day, an atmosphere of complete relaxation, and small town zen, grab your towel and lotion and head to Sullivan’s Island. You can walk this beautiful expansive beach for miles. Often times, depending on the tides, there are many wading pools for the little ones to play in.
IOP Beach Gear also delivers chair and umbrella rentals to Sullivan’s Island. For chair, umbrella, baby or beach game gear, you can make all rental arrangements with Beach and Games to Go. IOP Beach Gear also deliver’s to Sullivan’s Island.
Perhaps it’s the ambiance of this quaint town or the salt air, but food on Sullivan’s Island is tough to beat. Named after Edgar Allen Poe, Poe’s Tavern is a must do. Other fan favorites are the Obstinate Daughter and Mex 1.
If you’re a history buff visit the Edgar Allan Poe Library, Fort Moultrie National Monument, or the Sullivan’s Island Light House.
Everything Folly Beach
A destination all on its own, we can’t say enough about Folly Beach. No formal itinerary is needed, but here are some key notes below.
Pre-plan your beach day, rent chairs and umbrellas at Folly Beach Chair Rentals.
If you enjoy surfing or just watching, head to “the washout” on the eastern part of Folly Beach, known to surfers for the best waves in Charleston. If you’re not a surfer but want to give it a shot, be adventurous and take a surfing class with Shaka Surf School.
Looking to Kayak or SUP? A few options are below.
Kayaking and SUP is made easy with Coastal Expeditions. They have rentals and multiple guided trips where you will be sure to see Dolphins and all of the amazing wildlife that the waterways have to offer.
Charleston Outdoor Adventures is located right by Bowens Island Restaurant … COA and Bowens make a perfect fun, food and drink combination.
For those looking to rent surf boards, SUP, or kayaks for a day, or extended periods, reach to Folly Beach Adventures.
When you get hungry and thirsty in Folly, food is of no shortage, but we can’t deny our breakfast favorite is The Lost Dog Café. Lunch or night time fare is always best with a margarita in hand, in which we recommend Taco Boy for Mexican food and a funky atmosphere.
If you’re in the “Folly mood” but not necessarily the beach, don’t forget that our Charleston Park system, rents fishing pole rentals on the Folly pier. Fish or walk the pier with an ice cream to see some beautiful views.
Bike Folly! Cool Breeze Bikes is the original Folly Beach bike outpost.
Walking Folly makes us nostalgic about this hip island town with its fabulous vibe and casual flare. Take time to walk around, visit the shops, and stroll the pier. When the hunger hits, perhaps partake at one of the outdoor eateries including Chico Feo or Rita’s Seaside.
See both restaurants schedules for evening music offerings.
Looking for something casual but more upscale, The Blu Restaurant at The Tides Folly Beach Hotel is an excellent spot for that afternoon beverage or evening dinner while watching the sun set over the ocean view.
Mount Pleasant | West Ashley | Awendaw
So many call these beautiful towns, home. They also have many easy and convenient opportunities for fun. Over and above that ever popular movie, bowling, or mini golf day, here are a few ideas.
We love kayaking or SUP on Shem Creek where dolphin sightings are the norm. Both Coastal Expeditions (located by Shem Creek Bar and Grill) or Nature Adventure Outfitters (by Waters Edge Restaurant) provide tours and rentals.
Shem Creek water sports wear you out? Enjoy a casual meal at Vickery’s, Reds, or any of the Shem Creek waterfront dining options. For more upscale fare the newest Shem Creek gem is Tavern and Table.
Fishing is easy at the Mt. Pleasant Pier. Go the River Watch Café where they have made-to-order sandwiches, ice cream and smoothies. They have tackle sales and rod rentals. Order lunch, rent your gear, and spend the afternoon on the pier enjoying the breeze and the views of Charleston Harbor.
Visit a Plantation! Each Charleston plantation is so uniquely different. Be sure to visit them all. Below is just a partial list of our plantations you will want to add to your to-do list.
Middleton Place (W. Ashley area)
Magnolia Plantation (W. Ashley area)
Boone Hall Plantation (Mt. Pleasant)
Part of our SC park system and located on the banks of the Ashley River, Charles Towne Landing is a fun day for all.
The Old Village is home to Pickett Park where you can take a walk on the historic Pitt Street Bridge. See views of Ft. Sumter, Sullivan’s Island Light House, the Ravenel Bridge and Charleston Harbor. It is beautiful at sunset. If it’s breakfast or lunch time sure the partake in yummies at the Old Village Bakery. Dinner time belongs to the ever consistent, charming and delicious, Old Village Post House.
Hike the Palmetto Trail if you are in the mood for outdoor recreation. Head to Awendaw and hike or bike the Palmetto trail. Start at the Buck Hall Recreation Area trailhead. The trail begins at the Intracoastal waterway and takes you through the maritime forest offering views of Lowcountry salt marsh along Awendaw Creek. On your way, stop at the Sewee Out post and grab a picnic lunch. After your day of recreation, stop at the Sewee café for dinner on your way back to Charleston.
If your feeling even more outdoorsy and adventurous plan a trip on the Bull Island Ferry!
James Island | Johns Island | Wadmalaw Island | Kiawah
Planning a fun day? Venture out to the James | Johns | Wadmalaw | Kiawah Island areas. Here are a few tidbits to remember.
We can’t say enough about the SC park systems, most especially James Island County Park. Complete with playground, rock climbing wall, Splash Zone Water Park, disc golf course, dog park and bicycle, pedal boat and kayak rentals.
Tastings at the Firefly Distillery – Yep! Home of Firefly Sweet Tea Vodka, Firefly Distillery has tastings for the adults, and swings and farm animals for the kids to enjoy.
Charleston Tea Planation – Tour the only tea plantation in North America!
Angel Oak Tree – Free to the public, this 500-year-old tree is believed to be one of the oldest living things in the country.
Hungry? There is no shortage of great restaurants in these areas including Wild Olive, Fat Hen, Mondos, Sermett’s, and Roadside Seafood just to name a few.
If your desire is a scenic weekend drive and fabulous shopping, Freshfields Village on Kiawah Island is your destination.
Summerville | North Charleston
If you’re not eating at one of the yummy Park Circle Eateries or walking the Summerville Antique stores or relaxing in Azalea Park, these two areas also provide great Golf Course options.
We hope you have found some weekend or guest inspired inspiration. Tell is if so! We would love to hear feedback or your favorite Charleston day trip or night time fun itinerary. Publisher@OccasionsGuide.com.
Charleston is home to so many fabulous festivals, restaurants, and a continuously changing calendar of events. Check out up to the minute happenings at our fabulous Charleston Visitor Bureau.
If you are looking for the insider scoop of additional must-stop restaurants in Charleston, SC look no further than Eater.com (we think they are pretty spot-on!).