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

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Getting Around

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Things To Do

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Dont Miss

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Good to Know, Good to Go

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Special Things

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Where To Stay

Cottages on Charleston Harbor, Mt. Pleasant

OVERVIEW 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. Perfect accommodations for couples or families traveling together. THE ROOMS...…

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French Quarter Inn

OVERVIEW 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 are offered a glass of champagne and lady fingers....…

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Harbourview Inn

OVERVIEW 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 replicas of old Charleston features....…

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Where To Eat

Anson

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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Advance Search

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May 2020: Little Nell

This months featured property is… charming and sweet. THE ROOMS In 2017, Champalimaud Design refreshed all 86 rooms and suites and all guest floor corridors. The approach was to reinvigorate the spaces to be fresh, light and welcoming, utilizing palettes of blue, tan and grey to complement the relaxed nature of Aspen. Key features include… read more.

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