A Perfect Weekend in the Holy City

A Perfect Weekend in the Holy City

If you are like most of my clients you are traveling to Charleston fairly soon. Here are my travel recommendations for an amazing stay in the Holy City.
 
Tours
 
Taking a tour via the horse-drawn carriages is great - especially good as it beats the heat. The tour guides are very entertaining and have to be licensed (i.e. know their history) and generally have really good stories. Charleston is a city of good stories. You will not be able to pick the route of your tour - that is done randomly to keep the carriages from over-crowding specific areas. Palmetto Tours is our normal choice. Palmetto Carriage Works | Carriage Rides & Tours in .... There are walking tours hosted by The Preservation Society that I love. Link here. The Fall Tours - Preservation Society of Charlestonhttps://www.preservationsociety.org › events › fall-tours.
 
If you wish a private walking tour there is no one better than Walk and Talk Charleston. The "Lid Lady” Tyler not only goes through the history but also gives groups a real sense of what it’s like to live in Charleston. https://www.walkandtalkchs.com/
 
I’ve never taken a ghost tour where my kids didn't start heckling the tour guides. I don't think I’ve found the right tour yet (or maybe the right kids). Shoot for the graveyard tours if you are so inclined.
 
Things to Do
 
Ft. Sumter is a time commitment because the ferry time to get out there is 30+minutes - but being on the water is great in itself. Most people enjoy the ride more than what’s at the Fort because it’s minimal - but if you have Civil War enthusiasts with you they will be enthralled by the location and the distance the cannons were fired. One of the departure points for the Ft. Sumter ferry is from Patriots Point (bc that’s where Confederate Cannons were located!) and most of the people I take through the USS Yorktown love it as you can basically crawl all over it. They even let kids sleep overnight in the ship during the summer!
 
Pineapple Fountain and Waterfront Park. Behind Vendue Hotel on East Bay Street. Great for pictures and beautiful view across the harbor and out to Fort Sumter and Fort Moultrie.
 
Rainbow Row - quintessential Charleston. Series of thirteen colorful historic houses. The houses are located north of Tradd St. and south of Elliott St. on East Bay Street, that is, 79 to 107 East Bay Street.
 
City Market is a must see. Lots of cute stalls with Etsy-ish type shops.
 
In the market there is a Confederate Museum operated by the Daughters of the Confederacy. This in itself is the reason I find it interesting because you definitely know you are in the South. It's like walking through someone’s attic - but filled with Confederate memorabilia. A must for folks interested in Civil War - or people who like the weird vibe (me).
 
The Charleston Museum is a solid history primer of the city. The Gibbes art museum has great art collections and furniture from the city’s history (a good stop in if the weather is hot). A great stop on a rainy day or overly hot one. 
 
Best Plantation is Magnolia Plantation because the gardens are amazing. Take the tour around the property. Boone Hall is also good - and site where they filmed the Notebook - but gardens at Magnolia Plantation are the best. Boone Hall has a Wine Festival “Under the Oaks” in early December but you guys probably gone by then. Consider Drayton Hall Candlelight Tour - touring an old Mansion by Candlelight from 11/26 onwards.
 
Oyster Roast season is best in the cold months - but honesty it goes year round. Apparently the oyster farmers around here say the whole “season ending in “R” thing" is just made up (September thru April). Nothing is more low country that an Oyster Roast so its always great to find a group throwing one. As a standby you can always hit Bowen’s Island Restaurant - a Charleston staple since 1946. https://bowensisland.com/ More on restaurants below.
 
The beaches are great year-round - although the weather permits swimming from April through October. My favorite beach is Sullivan’s as it is a family beach (no development, no renting), you can park on the street and walk. Elementary School overlooking the beach! Best restaurant on Sullivan’s is the Obstinate Daughter - but Poes has best bar food. Folly Beach is a more traditional beach town vibe with funky beach bars and a boardwalk of sorts - but we usually go there only when the kids want to boogie board as the waves are good for surfing. Isle of Palms (a.k.a. IOP) fits somewhere in the middle.
 
Best EcoTours: Coastal Expeditions on Shem Creek hero-home.mp4 
 
There are Tiki Boats made to look like Tiki Bars. Obviously these tours are rented our by alot of the ubiquitous bachelorette parties - but I have freriends who have done it and they had a blast. More serious sunset boat cruises are always be great. Most of my friends have boats so I haven’t rented lately but I hear good things about a couple of sunset cruises. For under 6 passengers try this - Sea Glass Charters. For over 6 passengers I’ve always wanted to try these guys bc of all the things to do on the boat! (Skeet Shooting, Dance Bar!!) Osprey Boat Charters | Boat Charters Charleston, SCospreyboatcharters.com. The Schooner Pride is always a safe bet as well!
 
Check out the Candlelight String Concerts at the Unitarian Church (preferred) or the Cedar Room. Concerts are sometime classic rock tunes with string quartet all in candle lit room. The Unitarian Church is beautiful. 5b3db6ea-feba-11ec-80c6-1eb67b5178d0.jpg
 
Where to Eat
 
Food - Most important. Tons of great places - but here are the ones that come to mind.
 
Classic Charleston Upscale Southern (the Mainstays):
 
Husk - the original high end Southern Restaurant to catapult Charleston onto the restaurant scene. Always great - but restaurant snobs say the original chefs have left. Still a mainstay. Menu changes every day. Love Brunch there on the veranda. Great outside bar with Bloody Marys
 
SNOB (Slightly North of Broad) - always good. Newly redesigned interior. My wife’s favorite.
 
High Cotton - great room and jazz at night. Top end service and good for large parties. Like Magnolias it is on East Bay and in the middle of everything at night. Hit THE GIN JOINT cocktail bar across the street before.
 
Magnolias - Best Brunch EVER. You will need a nap after. Good Southern dinner.
 
The Ordinary beautiful room in an old bank - can be noisy - but amazing seafood. You go for the seafood.
 
Interesting/Off the beaten track
 
Chubby Fish - best seafood ever. I am not sure they have anything but seafood on the menu (not kidding). Small restaurant out of the way but this is where other chefs eat after work.
 
Harold’s Cabin - Bill Murray owns this quirky place. Sandwiches.
 
Edmunds Oast - brew pub - outside picnic tables are the best. Not near main tourist area though.
 
Poogan’s Porch - rent the porch if you can. Southern food served in a smallish Charleston single restaurant. Poogan was the dog that used to live on the porch.
 
82 Queen - great courtyard. The She Crab soup must be ordered.
 
FIG - menu can be limited in choices but fit for foodies. Chef uses local and obscure ingredients (Triggerfish). Not my favorite for large parties.
 
OTHER (awesome places that are not pretentious)
 
Leon’s Oyster Bar - you must go here. Oysters and Friend Chicken. Yeah, that kind of place.
 
Millers All Day - just like it says - breakfast all day and great diner food as well.
 
Rodney Scott’s BBQ - best BBQ ever. Carry Out. Must get the collard greens. Order ahead and pick up if you are sick of dining out.
 
Charleston Crab House - this is near the market and probably where my family and I have eaten the most in downtown Charleston. Large menu, reliable southern food, on a nice day can sit on the rooftop.
 
Callie’s Hot Little Biscuit - I cannot stress this enough - you must carryout for Breakfast. It will change your life.
 
Church and Union - brunch near market
 
Kilwin's Candy Shop (59 Market street). Awesome fudges and candies here. Great for a sweet tooth break.
 
Where to Stay
 
There are options to fit everyone's tastes and needs.
 
The Hip Ones:
 
The Loutrel - One of Charleston’s favorite new hotels. New Lowcountry style in great location. 50 Room Boutique Hotel. Rooftop terrace overlooking historic French Quarter. https://www.google.com/url?sa=i&rct=j&q=&esrc=s&source=web&cd=&cad=rja&uact=8&ved=0CDcQw7AJahcKEwjAy4yE2qf-AhUAAAAAHQAAAAAQAw&url=https%3A%2F%2Fwww.theloutrel.com%2F&psig=AOvVaw3Auf4QOo6dqs4vQF2RrRcs&ust=1681504354872445
 
The Dewberry. 60’s design cool factor. Elegant, elevated but fun. Rooftop for sunset cocktails and weekend brunch. https://www.google.com/url?sa=i&rct=j&q=&esrc=s&source=web&cd=&cad=rja&uact=8&ved=0CDgQw7AJahcKEwjQusOY2qf-AhUAAAAAHQAAAAAQBA&url=https%3A%2F%2Fwww.thedewberrycharleston.com%2F&psig=AOvVaw3Mc4FppXpWnlDCXzYmCUJO&ust=1681504404739617
 
The Pinch - News Cool Kid on King Street. Luxury. Boutique. https://www.google.com/url?sa=i&rct=j&q=&esrc=s&source=web&cd=&cad=rja&uact=8&ved=0CDcQw7AJahcKEwiIzuzVuKf-AhUAAAAAHQAAAAAQCQ&url=https%3A%2F%2Fwww.thepinch.com%2F&psig=AOvVaw2kUXN0RuCTouGJRq7qe9P2&ust=1681495407386275
 
The Restoration. Urban aesthetic, spacious rooms, great rooftop restaurant. Perfect attention to detail. https://www.google.com/url?sa=t&rct=j&q=&esrc=s&source=web&cd=&cad=rja&uact=8&ved=2ahUKEwjFwfbD2qf-AhVDlWoFHXsaARMQFnoECBQQAQ&url=https%3A%2F%2Ftherestorationhotel.com%2F&usg=AOvVaw0MrSetqzp26PmjD41JzY_b
 
Zero George. Romantic authentic Charleston fantasy. Restaurant tasting menu. Luxury boutique. https://www.google.com/url?sa=i&rct=j&q=&esrc=s&source=web&cd=&cad=rja&uact=8&ved=0CDcQw7AJahcKEwjIgey22qf-AhUAAAAAHQAAAAAQAw&url=https%3A%2F%2Fzerogeorge.com%2F&psig=AOvVaw3LjVsJq66gp8lbRqajgy6l&ust=1681504467453736
 
The Classics:
 
Hotel Bennett. Best view in city from rooftop bar and pool. Smart and sophisticated. https://www.google.com/url?sa=i&rct=j&q=&esrc=s&source=web&cd=&cad=rja&uact=8&ved=0CDcQw7AJahcKEwiQ7ozr3Kf-AhUAAAAAHQAAAAAQAw&url=https%3A%2F%2Fwww.hotelbennett.com%2F&psig=AOvVaw1_Ug1wwjzyp1U9oTLSBWY5&ust=1681505115149444
 
Charleston Place. A grand hotel that makes grand statements during the holidays. A community icon. https://www.google.com/url?sa=i&rct=j&q=&esrc=s&source=web&cd=&cad=rja&uact=8&ved=0CDcQw7AJahcKEwjA6tL83Kf-AhUAAAAAHQAAAAAQAw&url=https%3A%2F%2Fcharlestonplace.com%2F&psig=AOvVaw2KBRrU5xV85mzqWxgC3nK-&ust=1681505151276141
 
Off-Peninsula:
 
The Cottages at Charleston Harbor. Best kept secret. Across harbor from downtown. Amazing views, water taxi. https://www.google.com/url?sa=i&rct=j&q=&esrc=s&source=web&cd=&cad=rja&uact=8&ved=0CDcQw7AJahcKEwiwldLe3af-AhUAAAAAHQAAAAAQAw&url=https%3A%2F%2Fwww.thecottagesoncharlestonharbor.com%2F&psig=AOvVaw1fc0TYo4mYhVIJ4QVkRmFL&ust=1681505358070536
 
Post Inn (Mount Pleasant). Peaceful seaside village retreat. Like a step back in time. https://www.google.com/url?sa=i&rct=j&q=&esrc=s&source=web&cd=&cad=rja&uact=8&ved=0CDcQw7AJahcKEwiI5Or93af-AhUAAAAAHQAAAAAQBA&url=https%3A%2F%2Fwww.theposthouseinn.com%2F&psig=AOvVaw25gIwUBkCPhXK3IBOE_5zu&ust=1681505423132977
 
For Families:
 
Homewood Suites. https://www.google.com/url?sa=i&rct=j&q=&esrc=s&source=web&cd=&cad=rja&uact=8&ved=0CDgQw7AJahcKEwjAzIyGqKj-AhUAAAAAHQAAAAAQAw&url=https%3A%2F%2Fwww.hilton.com%2Fen%2Fhotels%2Fchsmshw-homewood-suites-charleston-historic-district%2F&psig=AOvVaw1MyOgvyBUBKRrwTi5BrDZQ&ust=1681525304532042
 
Hyatt Place. https://www.google.com/url?sa=i&rct=j&q=&esrc=s&source=web&cd=&cad=rja&uact=8&ved=0CDgQw7AJahcKEwj4_NOxqKj-AhUAAAAAHQAAAAAQBA&url=https%3A%2F%2Fwww.hyatt.com%2Fen-US%2Fhotel%2Fsouth-carolina%2Fhyatt-house-charleston-historic-district%2Fchsxh&psig=AOvVaw0zef3Xh0cPqg-sX5_utjsu&ust=1681525395352263
 
Other Articles
 
Articles that I trust on where to stay and eat in Charleston:
 
https://www.theinfatuation.com/charleston/guides/charleston-restaurants
 
https://www.google.com/url?sa=i&rct=j&q=&esrc=s&source=web&cd=&cad=rja&uact=8&ved=0CDgQw7AJahcKEwig4o3Dtaf-AhUAAAAAHQAAAAAQBQ&url=https%3A%2F%2Fwww.travelandleisure.com%2Fworlds-best%2Fbest-charleston-hotels-2022&psig=AOvVaw1-mI4n5vXoewp5JJT7qAC0&ust=1681494377550079
 
So those are my recommendations. Of course, nothing beats having your questions answered by a local, so please reach out and let me know if you have any questions, or if I can help you plan your trip! I am also available to show you the city and available homes if you wish to meet up with me while you are here.
 
Best regards,
 
-Kenton
Work With Kenton

Work With Kenton

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