Traveling to Charleston, SC - Jim Flynn's BestWeekends

Charleston, SC

Charleston, SC Overview

Charleston is that rare southern city that has retained the charm of its past while reinventing itself for the new millennium. This is a wonderful weekend getaway chocked full of great places to stay and eat and plenty to do. It is also one of those great walking around cities because you can discover something interesting down every alley and around every corner. Every time I go here, I stumble upon a new restaurant or boutique or gallery I never saw before. The anticipation of new discoveries makes this a delightful place to visit. The city is steeped in history, the Civil War started here at Fort Sumter, and a stroll through town, down cobblestone streets, among stately mansions evokes thoughts of days gone by.

Despite its charm and southern sophistication, Charleston has a bit of a quirky personality as well. How else do you explain that it’s against the law to cook a hamburger any way other than medium well? Or that the liquor in all the restaurants and bars used to be the little ones served on the airlines? The best reason we heard, true or not, for that was that Seagram’s makes all the little bottles and they were a major contributor to Strom Thurmond’s Senate campaigns…you can guess the rest. When he passed on, so did the little bottles!

My favorite Charleston quirk though, is the system for regulating where the horse drawn carriages go. Once the carriage is full, the driver pulls up to a gatehouse. The gatekeeper puts a little ping pong ball in an air bin (like the lottery) and the number that comes up is the area of the city the carriage can go to. They even put a special license plate on the carriage indicating where the carriage can go. I asked the gatekeeper how I would be able to get to a certain part of the city and he said, “gotta wait for that number to come up.” I said, “what if it doesn’t”, he said, “you gotta wait longer”, I said, “you mean I could come and pay 10 times and still not go where I want?” and he said, “yup” and I said, “doesn’t that seem a little strange to you,” and he said, “nope.” Ah, the South, you gotta love it.

What is wonderful about Charleston is that one visit isn’t enough. Even two or three wouldn’t allow you to enjoy all the area has to offer. Our hotels and restaurant recommendations are so pleasurable that you’ll want to enjoy them more than once.

When To Go

Summer can be very uncomfortable as the weather is hot and humid. The “seasons” for a weekend getaway are considered to be April/May and early June and September/October

Getting There

Charleston is a 3 1/2 hour drive from Charlotte, North Carolina, 5 1/2 hours from Atlanta, Georgia, 4 1/2 from Jacksonville, Florida and 2 1/2 hours from Savannah, Georgia. It is also accessible by air into Charleston airport from nearly any major in the country.

Getting Around

Charleston is an easy city to get around without a car. Most activities are within walking distance, Pedicabs (bicycle cabs) are also plentiful as are bike rentals. Uber is also an option. However, if you plan to play golf, go to the beach or visit one of the plantations outside the city, you will need a car. Bring your own or rent one for a day or so.

Things To Do

For a town with a population of only 100,000, the list of activities available is quite remarkable.


There are many excellent golf course in the Charleston area and two of the country’s greatest golf courses; Kiawah Island Golf Resort, The Ocean Course and Wild Dunes Resort on Isle of Palms. The Pete Dye designed Kiawah was the site of the 1991 Ryder Cup, was named “America’s Toughest Resort Course” by Golf Digest and earned 5 stars in its latest “Places to Play” survey. Two miles of oceanfront dunes rating a 29 out of 30 in the Zagat Top Golf Courses. Wild Dunes, a Tom Fazio course, is consistently rated one of “America’s Top 100” by Golf Digest and Golf Magazine. Considered to have two of the most beautiful finishing holes in golf. Relatively new to the area, Rivertowne, in Mt. Pleasant was designed by Arnold Palmer and is getting raves all around.


Family Circle Tennis Center, World class facility. Hard and clay courts. Opens 8am, 9 on Sunday. $10-$15 per hour.


Walking is great anywhere around town as your explore the little alleyways and streets. The Battery is a particularly nice place to walk and admire the houses and gardens. Waterfront Park is the perfect place for walking, running or biking. The Bicycle Shoppe, is the place for rentals.

Boat Rides/Rental

Pegasus Boat Charters & Tours. Charleston marine Harbor. Boats of all sizes and area tours.


Nature Adventures Outfitters, The only place to go if you like kayaking or canoeing. Has won all kinds of awards and accolades. Tours and self-directed.


Island Hopper Boat Charters. Fish in-shore, go shelling on Morris Island, crab for Blue Claws. This family owned business, led by Captain Randy Smith can do it all. 1/2 day fishing $250, 3 hour eco tour/shelling or crabbing $150. Sunset cruises 2 hours $125 for 4 people.


See our comments on the carriage tours in the Charleston introduction. They are still worthwhile even though you don’t know where you’ll go. Fort Sumter Tours, see where the Civil War began. Drayton Hall, the oldest preserved plantation house open to the public. Boone Hall Plantation and Gardens. America’s most photographed plantation. Edmondston-Alston House, Built in 1825 it is a wonderful example of the elegance of 19th homes in Charleston. Tommy Dew’s On the Market Walking Tours are fun and informative.  Very popular. See Middleton Place under “Special Things”


There are over 28 art galleries in the Charleston area, here are some that I have enjoyed; The Wells Gallery and Anglin Smith Fine Arts. Neema Gallery features original art and jewelry by southern African-American artists. Cannon Street Arts Center is a cultural facility focused on community-engaged work and houses a 110-seat theatre, a 1,500-square-foot flexible exhibition and gathering space, and a meeting room. Meyer Vogl Art Gallery is a contemporary fine art gallery, permanently featuring oil paintings by distinguished artists Laurie Meyer and Marissa Vogl, also exhibit works by a number of local and internationally recognized artists.

Charleston, particularly on King Street, is rich with amazing antique shops. Geo. C. Birlant & Co. is nationally known, Queen Charlotte Antiques has some of Charleston’s finest finds and the King Street Antique Mall has some 40 dealers over nearly 10,000 square feet of space.


The Farmer’s Market, Marion Square is a fun place Saturday mornings from April-December. Food, crafts, all kinds of great things. These are some of my other favorites, although there are a lot more. Duma’s Men’s Store. This is what men’s stores used to be like. Not much you won’t find here and much of it is unique. If Carrie Bradshaw (Sex and the City) lived here she would shop at Copper Penney Shooz. Stop in at the Mad Hatter, for, you guessed it…hats! Check out the exclusive candle lines at Candle Lover’s Delight.


Charleston RiverDogs, minor league team in the South Atlantic League.


The Charleston Museum, was the first museum in the country and charts the history of the low country. Gibbes Museum, houses a 7,000 piece collection of paintings, sculpture and drawings.The Provost Dungeon, is the story of Charleston and pirates and the like.

Right over the bridge in Mt. Pleasant is Patriot’s Point Naval & Maritime Museum. Tour a WWII aircraft carrier, a submarine, and a Coast Guard Cutter. Also the Congressional Medal of Honor Museum, the Cold War Submarine Memorial and a Vietnam Base camp.


Footlight Players, South Carolina’s oldest theater company performing in an old cotton warehouse.


Annual Festival of Houses and Gardens, March and April. 150 private historic homes in 11 colonial and antebellum neighborhoods. $45 per person.  Spoleto Festival USA, late May to early June.17 days and nights of 120 performances of opera, dance, music and theater in venues throughout Charleston.

Dont Miss

  • Fort Sumter
  • A carriage ride
  • The Battery and homes South of Broad
  • A walk down Legare Street
  • Middleton Place
  • Poe’s Tavern after the beach
  • Golf on Kiawah Island
  • Dinner at the Peninsula Grill

The Best Of...

News and Resources

Charleston Magazine. Everything Charleston.
Charleston City Paper. Home of the Annual “Best of Charleston.”
Charleston Visitor’s Board. Tourism site

Food & Drink


All of our Featured Properties offer breakfast, but for a change of pace try these: The Early Bird Diner is a local favorite with items like Pecan Fried Chicken and Cinnamon Waffles and Corn Cake Benedict. Sweetwater Café 137 Market Street. Great food and atmosphere. Open at 7am. Croissants, delicious coffee, perhaps a petit dejeuner, try the charming Gaulart & Maliclet, 98 Broad Street for a touch of Paris. Don’t miss Callie’s Hot Little Biscuits…so good.


Brunch: High Cotton brunch 11:30 on Saturday, 10am on Sundays. Have one of their famous Bloody Bulls with low country rub on the rim. Lunch: For dining outside I like the Pavilion Bar at the Market Pavillion Inn on the corner of East Bay and Market. Excellent sandwiches and salads and tremendous views overlooking the City.  Blossom on East Bay has a beautiful garden patio and excellent food. When the weather doesn’t cooperate I head to Cru Cafe, 18 Pinkney Street. Open kitchen, excellent wines and one of the best sandwiches I had in a long time…black forest ham, brie, caremelized onions on a baguette. Prohibition is a very cool place with amazing food and drinks. (corned beef hash is fantastic)  Other favorites are Virginia’s on King, both for the decor and the food and Butcher & Bee, amazing breads and pastries as well as locally sourced food items.


The Husk Burger tops most lists locally and nationally. Two Benton’s bacon-infused ground beef patties sit upon a house-made buttermilk & benne seed bun, topped with American cheese, diced white onions, bread & butter pickles, and a special sauce. Yum. Also, the roquefort burger with sea salt fries at 39 Rue de Jean, on John Street is amazing.


BBQ is a staple down here and their are lots of good places, but during our last trip I had the best brisket sandwich I ever had at Lewis Barbeque.

Oyster Bar

You could actually do an “oyster crawl” in Charleston. There’s Pearlz, Rappahannock, Hank’s and more but we like 167 Raw who has another outpost in Nantucket where we spend a lot of time. No reservations and the place is small, so get there early. The Champagne Bar at the Peninsula Grill is another favorite for oysters and a bit of bubbly. Also, The Ordinary, which also has an amazing selection of rum and rum drinks.

Wine Bar

Uncork features a high-tech Enomatic (self-serve) system that allows guests to choose from 40 different wines from across the globe in one, three or six ounce pour options. Cheese, charcuterie, sweets and small plates. Opens at 1pm on weekends. Charleston Grill and Peninsula Grill have Best of Award of Excellence lists as recognized by Wine Spectator.


Everyone has a martini bar, so where to go boils down to the setting. Here are my favorites; Inside and sexy: Thoroughbred Club at Charleston Place. Allen Lancaster at The Bar in the Spectator Hotel may be the best bartender in town and the bar is as sexy as it gets. Outside with Views; Pavilion Bar, Market Pavilion Hotel. Fantastic setting around a pool with magnificent views of the City. Schooner Pride, an authentic 84 foot Tall Ship, bring some cheese and crackers, they serve beer and wine on a wonderful 2 hour sunset sail. $20 per person. Sails all year except winter. Fleet Landing, 186 Concord Street, off East Bay. Right on the Harbor. Rooftop Bar at the Vendue Inn. Perfect setting for sunset. Killer dirty martinis. How could a bar called Prohibition not have great cocktails?  I don’t know whether I like Cane Rhum Bar more before or after dinner, but their selection of rhums is unparalleled. Relatively new to the scene,  The Belmont is a dark, sexy and romantic cocktail lounge with creative drinks and fun bartenders.

Coffee and Dessert

Kaminsky’s 78 N. Market. Here’s the perfect after dinner spot. Walk your dinner off and then enjoy a wonderful selection of coffees, pies, cheesecakes, cakes and specialty desserts. They even serve after dinner liquors, dessert drinks and dessert martinis. What a find!


Afternoon Delight

After a day of “tourist” stuff, I like a little snack…perhaps a glass of wine, at the end of the day. Here’s some great places to relax, have some cheese and crackers or appetizers and your favorite libation; The bar or garden at 82 Queen, 82 Queen Street or the bar or patio at Rue de Jean, 39 John Street. Great French bistro. Pearlz on East Bay. Opens at 4pm. Wonderfully fresh oysters. Have the oyster shooter…Absolut Peppar, oyster, spicy cocktail sauce…that’ll get you going. Gaulart & Maliclet, 98 Broad Street. French pates, cheeses, wine….cool setting.

While Away a Rainy Day

Poe’s Tavern, Sullivan Island. Casual, laid-back. Outside tables and bar. (with an overhang) Good appts and lunch. Tons of cold beers. Excellent Bloody. In town go to Tommy Condon’s Irish Pub.

After Dinner Fun

High Cotton, East Bay, has live jazz every night until 10pm, in a beautiful bar. Thoroughbred Club has piano music. Pavilion Bar, is where the beautiful people drink on nice evenings. Footlight Players perform top Broadway shows and Theater 99 is a comedy improv group. When all else fails head to the best dive bar in town, The Griffon. The Charleston Pour House has a full slate of live music.

Get Pampered

The go-to place for the ladies is Stella Nova in downtown Charleston. There are three locations for a spa, salon and store.

Wine Shop

We like Monarch Wine Merchants.  Unusual bottles and rare cuvée, Old World classics and a broad range of imports, Back Vintage bottles, Small batch wines from quality-conscious producers, Selections from cult producers

Picnic Fixins

Goat Sheep Cow has cheese, charcuterie, salads, sandwiches,,,,and wine!

Sweet Tooth

Main Street Sweets. An amazing selection of southern treats. Mail order catalog as well. Kilwins, for decadent chocolates and ice cream..

Special Things

Middleton Place

The spectacular Middleton Place with the most incredible gardens you may ever see, overlooking the Butterfly Lakes and the Ashley River is not to be missed when you are in the Charleston area. This old plantation is a National Historic Landmark and was first granted in 1675. You can take a tour (on foot, carriage or horseback) and learn about plantation life and the gardens. You can also kayak on the Ashley, take a guided nature hike, explore the Black Water Swamp or go horseback riding or biking. Have lunch in the restaurant on the grounds overlooking one of the ponds with Spanish Moss dripping from the trees and alligators peaking from the creek. This is not to be missed. Get there at opening (9am) and walk around. The scenery is just breathtaking. Plan at least a half day here.

Picnic Under an Old Oak Tree

And I do mean old! Said to be the oldest living thing east of the Mississippi, Angel Oak on Bohicket Road on St. John’s Island is a live oak tree estimated at over 1500 years old. It is about 65 feet high, has a diameter of 160 feet and is now owned by the City of Charleston. It has survived wars, floods, hurricanes and earthquakes. Today the park is a perfect place for a picnic. Stop at Saffron for picnic fixins and O’Hara & Flynn for wine and enjoy an afternoon “.under the old oak tree.”

Where To Stay

Cottages on Charleston Harbor, Mt. Pleasant

OVERVIEW of the Cottages on Charleston Harbor

One of the fun things about what we do is finding those undiscovered places that didn't show up in any of our research. Such is the case of the marvelous Cottages on Charleston Harbor in Mt. Pleasant, SC just over the bridge from Charleston.…

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French Quarter Inn

OVERVIEW of the French Quarter Inn

The 50 room French Quarter Inn is a sister property of the Harbourview Inn and overlooks the Market Square in the heart of the historic district.  Up the maghogany railed stairway from the street level, you enter a large richly appointed lobby and upon check-in…

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Harbourview Inn

OVERVIEW of the Harbourview Inn

The 52 warmly decorated rooms at the Harbourview Inn, in shades of brown, are spacious with 14' ceilings, triple sheeted 4 poster beds with luxury linens and coverlets, custom made armoires and original art. Many have overstuffed club chairs with ottomans. The large, European tiled baths are outfitted with…

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Planter’s Inn

OVERVIEW of The Planter's Inn

The Planter's Inn, with 56 rooms and 6 suites, is a delightful haven and ideally located in the center of the historic district. This Relais & Chateau property boasts exquisite rooms and a world class restaurant.


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Where To Eat


Located just off the market, Anson's is a sexy and romantic restaurant with hardwood floors, dark walls, chandeliers, crisp white table linens and sparkling taand pimento cheese.ware. beloved by locals and tourists alike, it is a must stop for your trip to Charleston Start with a drink at the handsome oak bar and sample one…

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Fulton Five

Ask the locals where their favorite place to eat is and more often than not, the answer will be Fulton Five. Hidden away on a small street off of King, this charming ivy covered trattoria has a big reputation for food, but remains casual and welcoming. There are only about 15 tables and a small…

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High Cotton

High Cotton gets my vote as the best overall restaurant in Charleston. They serve a delicious lunch/brunch on the weekends, have a excellent wine list (Wine Spectator Award of Excellence), a beautiful mahogany bar (where they serve a killer Bloody Mary and Bloody Bull with Low Country Spice Rub on the glass rim) and outstanding…

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Oak Steakhouse

When a steakhouse is done right it's dark and sexy, with a touch of elegance, has intimate seating and great food and wine. It's as perfect to close a business deal as it is for a romantic interlude. Not too many get it right these days....but the Oak Steakhouse in Charleston does. I've been lamenting…

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Peninsula Grill

From the minute you walk through the curved iron gate of the Peninsula Grill opening onto the side garden patio, you sense you are in for something special. Entering through a side door, you pass the beautiful dark bar, and reach a subtly lit, elegant dining room that reminds you of a very exclusive club.…

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Slightly North of Broad

I read an article recently where a New York restaurateur was complaining that restaurants that had been around for a long time get little attention from the press and critics. Everyone, he said, wants to talk about the "new, hot" place and they don't give any credit to longevity. Such is not the case in…

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