The Discerning Guide to Charleston

/The Discerning Guide to Charleston

The Discerning Guide to Charleston

One of the things we’ve noticed in all of our travels through the years is that something distinctive happens to a city when gentrification creeps in. It loses its coolness. It becomes polished and quaffed and glossy and the restaurants seem to take on a certain formula that involves subway tile and Moscow Mules. Georgia noticed this after she moved to Austin. What was once funky and textured has begun to feel manufactured. This is what happens when a city becomes extremely popular and developers can move in and make a killing without being reigned in.

Charleston feels a bit this way. For all of its historic charm and enchantment, and deep fascinating history, it feels like it could use some more character, that things could be a little less gentrified and a little more three dimensional. Don’t get us wrong, Charleston is a wonderful city to visit, but we wanted to write The Discerning Guide to Charleston to help you wade through the glossy stuff and get to the good stuff. There are many places that make “Top Lists” that we found very disappointing and comically expensive.

So here is our Eat, Drink, Stay, See, Acquire suggestions to help you uncover the enchanting and dimensional bits in Charleston. Let us know what yours are in the comments!


|The Discerning Guide to Charleston|

Best time of Year

Fall and Spring have the ideal temperatures and lots of historic tours and other happenings. Winter is a great time for all of the festivity and holiday spirit. This is a perfect town for a family to spend Thanksgiving or Christmas together.

Recommended Number of Days

4 days is plenty of time to walk or bike downtown at a leisurely pace while also fitting in shopping and sight seeing. You will also have time to rent a car for some day trips in the vicinity.

Recommended Number of People

1 to 4 people is a good group because it is an easy city for people to peel off and reconvene. Georgia visited as a solo getaway to refresh for a few days and it was perfect for that too. 

Apps to Download

Historic Walking Tour gives you an audio guide to stroll around the city. It is worthwhile in order to get a feel for the deep history of the place. 

Eat, Drink, Stay, See, Acquire


  • 167 Raw was our overall favorite meal in Charleston. It is a small seafood bar around the corner from Zero George that serves up pristine fresh seafood. Ask for a few oysters of their choosing and get the lobster roll. Both were among the best we’ve ever had.
  • FIG is our top spot for dinner. You need a reservation but it’s worth it. Have the fish stew, it’s sublime.
  • Xiao Bao Biscuit is one of the few Asian restaurants in town. It has a small vibrant menu, good value and great vibe. Try the bean paste fried chicken.
  • Callie’s Hot Little Biscuit is known for its array of incredible biscuit flavors (if you stay at Zero George, they will serve them at breakfast)
  • Hominy Grill is a heavy duty breakfast or brunch spot if you want a serious Southern meal.
  • Leon’s Oyster Shop for fried chicken, oysters and champagne, quite a combo!
  • Rodney Scott’s BBQ is a legendary staple if you’re in the barbecue mood.
  • Chez Nous is a very small intimate spot, with a changing menu daily, good for breakfast or lunch.
  • McCrady’s Tavern is a Charleston staple and has a very cool menu. On a visit there many years ago was the first time Georgia had venison served in a restaurant, before it became more available on restaurant menus.
  • Butcher and Bee is a Mediterranean-style, vegetable forward menu with an open kitchen. They have an interesting drink menu including red chai with almond milk, lavender latte and green juice. We tried the rice bowl with eggs vegetables and almond butter. It was a very interesting combination of flavors, but not exciting enough on its own to make you leave feeling you experienced the menu. This is the kind of place to go with others so you can share bites of things.
  • Sugar Bake Shop is a great spot for a sweet treat on Cannon Road.


  • Five Loaves Cafe green juice bar is a great afternoon pick-me-up instead of coffee. Ask for their green drink minus the apple juice for a super green afternoon boost.
  • Black Tap Coffee  (try the Iced Lavender Latte)
  • Electric Cafe and Vinyl
  • Vintage Coffee and Cafe
  • Gin Joint, ask for the bartender’s choice


King Street is known to be the main retail drag but it is now a lot of chain retailers and feels very touristy. There are some diamonds in the ruff though:

  • Blue Bicycle Books for an early edition Hemingway or other classic. Perusing the signed edition copies is really delightful
  • Juxtaposition on King Street is a small boutique with unique items you’ll want to take home
  • J. Stark for hand made bags and totes
  • Corneau Goldsmithing is a beautiful jewelry company on a side street off of King Street. The owner Michael Corneau can often be found inside working away on his amazing pieces
  • Workshop Building Art Co. is a place for architectural salvage slightly north on King Street in a more industrial area. It is small but like a little treasure chest


  • Take a bike from your hotel or rent from one of the Holy Spokes city bike racks around town and cruise around South of Broad to see Rainbow Row and all of the amazing houses. You can use a bike to make other stops to historic home tours too if you have a bike from a hotel with a bike lock
  • The historic Dock Street Theatre in Charleston’s French Quarter is particularly enchanting to stroll around.
  • Tour a Historic House or Plantation. There is a combined ticket for the Aiken Rhett House and Nathaniel Russell House which we would recommend. The Aiken Rhett House is particularly beautiful and storied
  • Rent a car for 24 hours from the Enterprise right downtown and visit Magnolia Plantation, Middleton Place or Boone Hall
  • Visit the Beach at Sullivan’s Island while you’ve rented your car as well and have lunch at Obstinate Daughter (they have a tasty shrimp roll)
  • And be sure to visit the Angel Oak Tree on Johns Island


  • Zero George is currently our top choice.  It feels like visiting your great-aunt who has impeccable taste and knows how to make really good biscuits in the morning. It comes with so many perks, including free bikes to cruise around town (you definitely won’t need to rent a car for most of your time if you use this), as well as a complimentary evening wine and cheese happy hour, and the most incredible breakfast each morning. It’s a hotel experience that is unlike any we have had before because of the historic charm mixed with attention to personalized detail.
  • 86 Cannon is a beautiful house on Cannon Road a bit removed from the main drag which is fine by us. A couple renovated an historic home and turned it into beautiful rooms comparable to what you would get at Zero George.
  • The Dewberry looks a bit like a 50s prison on the outside but on the inside feels very Mad Men. It was recently updated and if you want a more grand feeling hotel it has a great vibe.
  • Belmond Charleston gives you a super luxurious room in a very grand feeling hotel. It’s a very different feeling than our first two recommendations which are more intimate.
  • The Restoration combines historic charm with modern amenities in a very good location.

Did we not mention your favorite place in Charleston? Leave it in the comment section!

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  1. Chucktowner February 26, 2018 at 2:54 am - Reply

    Thank you for sharing this great information! Great tips!

    • adventuregetaways March 18, 2018 at 1:01 am - Reply

      My pleasure! I’m glad you’ll get use out of it.

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