First Time Visiting Charleston, South Carolina

Visiting a new place for the first time always feels exciting. Charleston, South Carolina had been on my list for years, but the timing never worked out. Other destinations always took priority, and the long flight time made it less appealing. Since there’s no direct flight from my city, the trip required a connection and ended up being almost seven hours in total.

Waterfront Splash Fountain

Why Charleston Became the Destination

The original plan was to attend the Macy’s Thanksgiving Day Parade in New York during Thanksgiving week. Those plans fell through when my mom’s November travel schedule changed. She was going to be in town for Thanksgiving, and her birthday happened to fall right on the holiday.

After last year’s lesson, I knew I needed a mental break. With New York off the table, I looked for an alternative. Charleston quickly became the front runner.

Timing the Trip

I tried to line up the trip with Charleston’s Food and Wine Culinary Event in the second week of November. Unfortunately, my travel buddy couldn’t adjust his PTO as his vacation days had already been allocated at work. Luckily, his first-week-of-November plans also fell through, so we decided to make the most of that window. Thankfully, I was able to take those days off too.

Concerns About Traveling South

I’ll admit I was hesitant about traveling to the South in today’s political climate. Many cities have racially charged environments, and I wasn’t sure what to expect. Still, I chose to stay positive and hoped for the best.

Adjusting the Itinerary

The original plan was four nights, but Charleston hotels are expensive. Flights, on the other hand, were fairly affordable. To save money, we booked a red-eye flight. That gave us a full day in Charleston while cutting one night off the hotel stay.

Travel Complications

Just a week after we booked, the senseless happened: the government shutdown. Normally, shutdowns come with the reassurance that workers will eventually get retroactive pay. This time, there was no such guarantee. Air traffic controllers were stretched to the breaking point, some stopped showing up, and the administration even cut back flights.

For someone already anxious about flying, this felt like a nightmare scenario. Headlines warned of exhausted controllers making critical decisions on little sleep, and stories circulated of flights being delayed or canceled without warning. I couldn’t shake the thought of being stranded mid-journey, stuck in an airport with no way home.

The worst part? Our tickets were nonrefundable unless the airline itself canceled. That meant we had no choice but to press forward, knowing we were stepping into a travel situation that felt unstable, unpredictable, and almost unbelievable.

Planning the Trip

I didn’t do much research on attractions. I had hoped to join a free walking tour, but those aren’t common in the U.S. Instead, I found a blog with maps, directions, and photos of walking routes through Charleston’s districts. It looked manageable, so I decided to rely on that.

Where I did put effort was food research. I love Southern cuisine, and was eager to discover Charleston’s flavors. I came across a few restaurants that caught my attention and also uncovered local favorites in Charleston.

A Different Kind of Travel

For once, I didn’t over-plan this trip. I usually prepare backup itineraries, but this time I kept it flexible. Darwin, my travel buddy, isn’t a planner and didn’t even ask about an itinerary. On most trips that would spell trouble, but he actually kept us on track and made solid choices when needed.

Something about this trip felt different. Even without a detailed plan, the day went smoothly.

First Impressions of Charleston

Our first day ended with no stress and no real concerns. Charleston is a visitor-friendly city, and going with the flow worked perfectly. What started as a trip full of uncertainties turned into a great beginning to our adventure.