Suzy Leonard
For FLORIDA TODAY
Aug. 22, 2026, 5:02 a.m. ET
- A group of friends successfully planned a trip that originated in their group chat.
- The friends traveled to St. Augustine, Florida, for a weekend getaway.
- Their trip included dining, a trolley tour, and visiting a speakeasy.
- The group stayed in rented houses in the Davis Shores neighborhood.
“We made it out of the group chat!”
My friend Tori said this recently, and at first, I was nervous.
I’m no stranger to group chats. I’m in several with friend groups and former work colleagues. Tori and I are in one with our menfolk and two other couples, as well as another with just us girls so we can discuss feminine things like yoga classes, weekend plans and our menfolk.
But in my experience, leaving the group chat isn’t a positive. It’s more a sign of frustration, stalking out of a room because the conversation got annoying.
“The trip,” she said, noticing my confusion. “The trip made it out of the group chat!”
It’s good to have 30something friends who can translate modern vernacular.
It’s also good to have friends who are willing to do the work to make a text conversation a reality.
Our destination was St. Augustine, and we arrived ready for adventure, with about 40 hours to soak up all the Florida history, touristy kitsch and delicious food we could.
You can squeeze a lot into less than 2 days
We gobbled up great meals at Blackfly The Restaurant and the St. Augustine Fish Camp.
We embraced the tourist life with a manic trolley ride and even managed to learn a few things. When the average temperature isn’t set on broil, I want to revisit Lincolnville, a charming community founded in 1866 by former enslaved people that became a pivotal part of the Civil Rights Movement.
We survived an overly emotive tour guide at the Old Jail, and though I got locked in the bird cage, I managed to escape in time for a short nap before dinner.
I’m glad I got a little rest, because dinner at Odd Birds Cocktail Lounge and Kitchen was more an experience than a meal. We arrived just in time for our 8 p.m. reservation and were led behind a bookcase into the dim, tropical oasis that is Charlotte 33 Speakeasy. Low, moody music played in the background, and bartenders crafted personalized cocktails for each of us. For a couple of hours, we escaped reality, taking time to concentrate on the ambiance, flavors and friendship.
After dinner, we weren’t ready for the night — or the weekend — to end. We took our time walking back to the house, then gathered around the dining table for a few rounds of Herd Mentality, a silly and hilarious board game.
But, alas, reality has a way of recapturing its escapees.
As we drove home, the chat group lit up again with shared photos and declarations of mutual admiration.
I’m so grateful the trip made it out of the chat. Is it too early to start chatting about the next one?
Suzy Fleming Leonard is a retired journalist who spent 25 years as a writer, editor and columnist at FLORIDA TODAY. Reach her at suzy@321creates.com.
