The Mid Life Dating Files 2025

Name an attraction or town close to home that you still haven’t got around to visiting.

Savannah, GA: The Place I’ve Somehow Avoided Like It’s an Optional Field Trip

I have been a lot of places. Like, a lot.

Yet somehow—some way—I have never been to Savannah, Georgia.

Make it make sense.

Savannah is close enough for a solid road trip, dripping in history, filled with old mansion homes, haunted vibes, Spanish moss, charming squares, and located on the East Coast near approximately a million other places I’d also like to visit. And yet… here we are. Still Savannah-less.

My First Savannah Memory (AKA: Why This City Lives Rent-Free in My Head)

My very first recollection of Savannah doesn’t involve me at all—it involves my parents.

I was in high school when they went with a group of friends. They came back with stories. Not casual vacation stories—legendary stories.

Specifically, the story where they met Lady Chablis from Midnight in the Garden of Good and Evil.

Yes. That Lady Chablis.

The iconic, show-stopping drag queen who performed for decades at Club One.

According to my parents (and their friends, who will never let my dad forget it), Lady Chablis was all over my dad—sitting in his lap, flirting, entertaining, and generally living her best Savannah life—while my mom and their friends were absolutely dying laughing.

Then… someone took pictures.

Bad move.

Lady Chablis did NOT want photos taken.

She reportedly went from fabulous to furious in about 0.3 seconds and proceeded to chase one of their friends around the establishment trying to grab the camera and force her to delete the pictures. Full-on pursuit. No mercy.

My dad? Mortified.

My mom? Cry-laughing.

Their friends? Still telling this story decades later.

And honestly… if that isn’t the Savannah vibe, I don’t know what is.

Naturally, this story made me want to:

Go to Savannah Watch the movie See everything that city has to offer

And yet… I still haven’t gone.

The Savannah I’ve Built Up in My Head

When I picture Savannah, I picture myself wandering through the Savannah Historic District, making my way past Reynolds Square, soaking in the history, and eventually landing at the iconic Forsyth Park fountain—probably pretending I’m in a movie montage.

I want to:

Ride through old historic cemeteries on a toured golf cart (because walking is fine, but riding feels more Savannah). Visit Johnson Square, the city’s oldest public plaza, and admire all the gorgeous architecture. Stroll through Wright Square, stopping to appreciate the memorial to William Washington Gordon. Stand outside the Hamilton-Turner Inn, mainly because Turner is my last name and I feel like it’s destiny.

Then I’ll wander:

Down Jones Street, because everyone says it’s one of the prettiest streets in America. Over to Monterey Square, where I’ll find a quiet little oasis and mentally plan my early retirement. Past elegant mansion homes like the Mercer Williams House and the Armstrong House, pretending I’m casually house shopping.

You know. Normal things.

Boats, Dolphins, and “Yes, I’ll Take the Tour”

Because Savannah doesn’t stop at land, I’d also like to:

Take a dolphin boat tour (because dolphins = joy). Hop on a riverboat cruise, preferably with a drink in my hand and zero responsibilities.

And Then… Tybee Island Happens

Because why stop when you can keep going?

Just a short drive away is Tybee Island, which I’d also love to stay at—extending the vacation because I make excellent life decisions.

Tybee Island was featured in that Miley Cyrus movie (The Last Song), and the beaches and scenery looked absolutely beautiful. Sun, sand, ocean views, slower pace… yes please.

And while we’re already in that area, let’s just casually mention that Hilton Head is nearby too—and I’ve always wanted to go there as well.

At this point, it’s not a trip.

It’s a multi-stop adventure.

The Ideal Plan (AKA: My Travel Personality in a Nutshell)

Here’s how I see it going:

Start in Savannah for history, charm, and walking tours. Eat at hole-in-the-wall restaurants. Visit dive bars and mom-and-pop places. Drink good wine. Find a few breweries. Be spontaneous—but with a list. Immerse myself in history. Then move on to beach views, relaxing vibes, and good food and drinks.

Basically:

Culture ➜ Coast ➜ Cocktails

So Why Haven’t I Been Yet?

That’s the real mystery.

Savannah has everything I love:

History Beautiful architecture Stories that turn into legends Nearby beaches Amazing food and drinks

And yet… I’ve still never made it there.

But honestly? That just makes the eventual trip even better.

Savannah, I’m coming for you.

Eventually.

Probably with walking shoes, an appetite, a loose itinerary, and a very strong appreciation for a city that once traumatized my dad—in the best possible way.🍷🐬🍝🍻🚗⛴️🗺️📍