Ten Days in Charleston, Savannah and St Augustine January 3–13, 2026
We’ve always looked at winter in the upper Midwest as a season to hibernate, a time to do the things pushed aside the rest of the year. Build several puzzles in a week. Binge-watch Band of Brothers over the Christmas holiday (yes, every year). Spend hours in the train room. Work on art journals.
But we’ve learned that one of the best times to travel is right after the holiday season.
Most people have finished the family rounds or fought airport crowds to reach warm beaches or snowy mountains. Life returns to its regular rhythm. Hotels and VRBOs are easier to book, restaurants are eager to fill tables, and points of interest feel calm again. Tours are simpler to schedule. Everything breathes a little.
Having visited both Charleston and Savannah on separate occasions, we decided this time to experience them in the same trip and add St. Augustine for comparison. Early January had served us well during our pre-retirement years, and once again, it didn’t disappoint.
Charleston
Our flight from Madison to Atlanta was easy, with the added bonus of visiting a couple of our Sweet Littles. From there we picked up a rental car and headed to Charleston, arriving Saturday, January 3, 2026. We settled into our charming VRBO, grabbed dinner, and called it an early night.
Sunday found us in Old Town Charleston in search of brunch. Success came in the form of Rudy Royale and a fabulous Bloody Mary. Brunch was followed by a leisurely afternoon wandering art galleries, strolling the Battery, and walking the genteel streets of a city we really enjoy. That evening, we dined at Wild Common, one of Charleston’s Michelin star restaurants. We were seated at the bar which allowed us to watch the chefs at work and visit with the bartender. The bartender shared stories with us about the restaurant, and yes, the food absolutely earned the star. Content, we returned to our VRBO.
A Lovely Day of Tours and Exhibits
Monday began with coffee and another venture into Old Town for tours, including an excellent carriage ride with Palmetto Carriage Tours, lunch at Henry’s, and the Rembrandt exhibit at the Gibbes Museum of Art. A rooftop cocktail rounded out the day before heading back to the VRBO once again.
Savannah
Tuesday was transfer day to Savannah. I woke up sick, so Michael drove while I slept. We checked into the JW Marriott Savannah Plant Riverside District, a stunning property that’s worth visiting even if you don’t stay there. The building itself houses an impressive collection of artifacts and curiosities, including a replica of the largest dinosaur discovered to date.
Unfortunately, I was completely down and out and spent the next two days in bed. We upgraded to a room overlooking the Savannah River, which at least offered a front row view of massive ships moving through the third largest port in the United States.
Wednesday, I dragged myself out of bed (poor me) to join Michael on a walking food tour I’d booked with Savannah Taste Experience, and it turned out to be one of the best experiences of the entire trip. Our host and guide, Shannon, was delightful and knowledgeable.
Wednesday, I dragged myself out of bed (poor me) to join Michael on a walking food tour I’d booked with Savannah Taste Experience, and it turned out to be one of the best experiences of the entire trip. Our host and guide, Shannon, was delightful and knowledgeable.
St. Augustine
Friday brought another travel day, heading toward St. Augustine via Tybee Island and the National Museum of the Mighty Eighth Air Force. Our next VRBO sat directly on the ocean. Still not fully recovered, I felt an almost immediate sense of healing from the salt air and rhythmic waves.
Our friends Jim and Rachelle joined us on Saturday for the weekend, and it was truly a blessing catching up.
They served as generous tour guides. Sunday included another food tour with First Coast Cart Tours, this one beautifully layered with history and culturally appropriate dishes. A relaxed afternoon and another wonderful evening with friends followed.
Atlanta and Home
Monday was the drive back to Atlanta, a flight home, and arrival that afternoon.
The goal of this trip wasn’t simply sightseeing. It was practice. We wanted to learn how to pack for longer trips, manage expectations, and enjoy each day as it came. What happens when you forget something you truly need? How do you handle three unexpected days confined to bed despite prepaid plans? What about cold, rainy weather you didn’t anticipate or pack for? And the big one, how do you keep from overpacking?
We aren’t new to travel, but given the pace we’ve set for ourselves in the next few years, efficiency and intention matter more than ever.