Escape from New York

Enchanting Charleston

Editor’s Note: This article is part of our series “Escape from New York.”  Series Overview: Flight times are within 2 hours and 30 minutes of New York City.  Spend 48 hours immersing yourself in the culture and feel of the destination city.  Flights can depart at 6am on Saturday and arrive back in New York on Monday morning so you can attend your first meeting of the day.  Previous articles include: trip to the Niagara Fall region in western New York and 48 Hours in Chicago.

I decided to head down south to the city of Charleston, South Carolina.  Flight times come in just under 2 hours (2 hours out and 1.5 hours back!) Having never been to Charleston, I chose to stay downtown in the historic district to be close to landmark locations on my list of places to see.

I learned a few things on my trip to the Palmetto City.  First and foremost, Charleston is a city that forces you to make a lot of decisions.  Shall I get another order of Shrimp and Grits?  I already tried She Crab Soup, but should I get another bowl.  Do I spend a day on a boat in the harbor or walking around taking pictures and visiting historical landmarks around town?  An afternoon on the beach or marshland?  Fishing or Kayaking?

In Charleston, the decision points you have to make are all positive.  And 99.9% of the time, the answer is yes (and you can actually fit in a lot over the course of 2-3 days.)

Day 1:

Is ‘raining buckets’ still a phrase people use? Well that happened, but a little (or tons) of rain wasn’t going to stop me from walking around the city.  Plus it’s a fun experience to have neighborhoods to yourself when exploring.

Rain is also a perfect opportunity to try out some of the local coffee shops and read for a bit or just relax and enjoy the downtime.

I also learned the city carriage companies operate rain or shine.  I took a nice hour long ride with the Old South Carriage Company which provided great background information on one of 3 historic districts downtown. (I was also informed the horses are constantly rotated out to their large pasture right outside of the city which is good to hear.)

I finished the day with dinner at the restaurant Husk.  I had seen the owner and chef Sean Brock on Mind of a Chef and his passion about southern food culture and preserving food traditions really stood out and it carried right through to the dinner.  Great meal, service and atmosphere (the restaurant is a Victorian era home and they have a separate house next door which serves as a bar.)  The separation between bar and restaurant is a cool setup and I would recommend an early arrival to grab a drink before dinner.)

Charleston properties:

Day 2:

I walked 10.5 miles my second day in the city.  Because why not.  Bottom line, Charleston is a very walkable town and you can criss cross streets, stop along the way to visit historic landmarks from the Revolutionary and Civil Wars, visit churches and graveyards.  A short list included the Aiken-Rhett House, Aquarium and the Old Slave Mart Museum.

I ended the day on the harbor with a 2 hours sunset cruise on Schooner’s Pride.  Alcohol  was available for purchase and it felt right to try a locally produced beer and glide across the water.

Harbor Sailing:

Day 3:

I extended my trip for half a day due to flight times and my desire to not get up early to head back to NYC. Having walked over 10 miles the previous day, I reserved a Zip Car for 3 hours and headed over to Folly Island (Folly, not pronounced like Matt Foley…who lives in a van…down by the river.)  The $30 for the car was well worth it to get out and explore the outer city limits.


Here’s the triple bottom line: it’s all good so go for it, it can be a bit heavy, pace yourself.  I purposefully toed the line of gluttony (and will attribute it to writing this article.)  If you are on vacation, why not explore the best a city has to offer.  And not everything has to be expensive but if a city is known for a dish, give it a try.  The short list included: She Crab Soup, Shrimp and Grits, Shrimp Po’boy, Oysters.  Basically a lot of pork and seafood which is right up my alley.

Husk Dinner on the top and Poogan’s Porch Dinner on the bottom.  


A great mixture of hoof (carriage ride,) a lot of walking, boat, more than a few Ubers but with an average cost at $5.50/trip.  I could have easily rented a bike and thrown that in as well but felt pretty well covered.

*I reached out to the Charleston Area Convention and Visitors Bureau and they supplied entry into some of the museums, rides and sailing I did on this trip.  They have a helpful website and it is worth checking out in advance of your trip down south.

Leave a Reply

This site uses Akismet to reduce spam. Learn how your comment data is processed.