4 Days in Historic Charleston, SC

Charleston, SC dazzles – how to wrap it into four days? The choices are overwhelming! To design the perfect girlfriends reunion weekend – and get the choices we wanted – we applied a tried-and-true travel template from our years as seasoned Womentravelers:

  • We started planning and making key decisions, such as preferred dates, accommodations and airline tickets, 6 months ahead. In a popular destination like Charleston, particularly at peak or near-peak seasons, it’s necessary to start early to get what you want – and “travel on your own terms.”
  • Living in various regions of the U.S., we divided up the planning responsibilities and coordinated almost daily by email.
  • And, rather than getting buried in an overwhelming pile of magazine clippings, brochures, web links and social media tips, we focused on the most important decisions, prioritized them and, after some quick online or friendsโ€™ research, made our choices within a few days.
  • Then we left the rest to serendipity.

It was a fantastic trip! We felt fully immersed Charleston’s timeless charm, without micro-managing our itinerary and still leaving time for relaxation, shopping and a glass (or two) of wine.

Here’s our proven formula:

  • Budget: We agreed on a budget that worked for each of us and all of us (including air travel), because that frames everything.
  • Accommodations – Two girlfriends accepted the task of scoping out hotels, B&B or houses online in various neighborhoods of the city. With a little research on VRBO and AirBnB, in addition to travel resources like Explore Charleston (the cityโ€™s official visitors guide) and Travel & Leisureโ€™s Charleston Travel Guide,ย we quickly decided that we wanted a house and confirmed the best timing โ€“ in our case, September/October โ€œbridge seasonโ€ โ€“ that kept to our budget and typically offered pleasant weather.

From our initial list of about a dozen options and features, we narrowed the choices to #1 and #2 (through email “voting” and in part with tips from friends who’d been to Charleston). That meant diving deeper into details about โ€œLarge Home Downtown Charlestonโ€ and โ€œMadison Complex.โ€ By reviewing the options, we also found we could rent an affordable property, in-town, with separate bedroom-bath suites for each of us. And with refundable bookings.

Weโ€™re past the years of dorm-style accommodations and share bathrooms whenever possible.

We also found that agencies, such as Charleston Vacays, list their properties on VRBO. Ultimately, thanks to their quickly responsive email and telephone communications, we chose one of their listings (โ€œMadison Complexโ€) in the Cannonborough Elliotborough district, about a mile north of the central historic district and an easy walk that added even more features to our experience. (We found Charleston Vacays easy to work with, professional, timely and customer friendly.)

  • Dining – We secured our top choices ahead of time for dinners, and cancelled within the typical 24-hour window if we found something more intriguing.ย The early planning was a life-saver, because bookings can be tight in Charleston; we also swapped out a couple of choices after we arrived based on what we found onsite.
  • Getting around – With some of us driving and some flying, we decided to use our personal cars and Uber if needed.ย Mostly, we walked.
  • Everything else – Naturally each of us had different extras in mind – including excursions, carriage rides, art galleries or shopping. So we made a common list, and negotiated each day according to weather, mood and “what came up.”

Oh, yes, and our formula now has a Plan B step. We also learned rather suddenly that itโ€™s essential to have a game plan for the unexpected. (Who would have anticipated that a hurricane would decide to head straight to Charleston while we were there??) Sadly we had to abruptly leave town, scramble for flights and rental cars, abandon our wonderful vacation home and miss out on our last dinner (planned for Magnolia) in a matter of hours. And good we did โ€“ Hurricane Ian made landfall in downtown Charleston and produced significant flooding.

Meanwhile, here are our โ€œbest ofโ€ Charleston picks for Low Country cuisine or other culinary specialties โ€“ and weโ€™d return to these anytime:

SNOB (this was the fave of my friends, although I didnโ€™t arrive until later that evening) – Slightly North of Broad is an eclectic Low Country experience with white table cloths and impeccable service to match the delicious food, another offering from the well-known Hall family whose Halls Chophouse in Charleston, Columbia and other Southern cities are the go-to choices for every day fine dining and birthday celebrations. 192 East Bay Street, Charleston, SC. 29401, tel: 843-723-3424.

The Vendue Rooftop โ€“ 360-degree views of downtown historic Charleston and miles beyond, with light fare (tacos, quesadillas, sandwiches and poke bowls) and no reservations needed. This was a good choice after our carriage tour and visiting art galleries along East Bay Street. Location: 19 Vendue Range, Charleston, SC 29401, tel: 843-424-2337.

Estadio โ€“ weโ€™d had a full day of touring and lunch, so this Spanish tapas restaurant with shared small and large plates was perfect for the options we needed, right down the street in our Cannonborough Elliotborough neighborhood and very inventive in flavors and a deliciously fun evening! It w Location: 122 Spring Street, Charleston 29403, tel: 843-793-1029

High Cotton โ€“ another Hall family venture, High Cotton is one of the emblematic high-end restaurants for Low Country cuisine. We dressed up, dined in a comfy banquette surrounded by brick walls, beautiful art and pine floors and, in addition to the exceptional cuisine and wines, enjoyed first-class service.

Here’s what we found delivered Charleston highlights for daytime touring on our schedule. Explore Charleston and Get Your Guide are ample resources for planning your stay:

  • Charleston City Market was worth a stroll but very touristy; most of what we found was regional, such as the Southern Sweetgrass baskets and decor, but there was also some of the standard kitsch familiar in county fairs and urban street vendors, so shop with care if you’re looking for something local.
  • Virtually any of the Carriage Tours is worth a few hours; we used Palmetto Tours โ€“ in small groups or privately, these tours provide an entertaining way to see downtown Charleston. The tour guides are extremely knowledgeable and often characters with their own individualized scripts. In sum, it’s an easy way to embrace the city’s historical highlights and discover neighborhoods to return to on your own. Be sure to book these popular tours ahead, and check out the several variations (daytime, evening, haunted and more).
  • Self-guided walking tours โ€“ downloading this app on our iPhones, we spent a few hours walking through residential historic Charleston, with its enormous gracious homes, some dating to the 1700s, churches, gardens and cobblestone streets in the area South of Broad. There is a broad selection of walking tours from which to choose.
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